Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

Four-Week Florida Travel Route

Day 1 · Wed, Mar 25
Miami, FL

Arrival in Miami

  1. Pérez Art Museum Miami — Downtown Miami; contemporary art and bay views, afternoon (~2 hours).
  2. Bayside Marketplace — Downtown; waterfront browsing and an easy first meal, late afternoon (~1 hour).
  3. Joe’s Stone Crab — South Beach; iconic Miami seafood dinner, evening (~1.5 hours; ~$50–90 per person).

Afternoon — Art by the Bay

After checking in, head to Pérez Art Museum Miami in Maurice A. Ferré Park. From most Miami hotels, a rideshare is simplest; allow roughly 15–30 minutes depending on traffic, and ask to be dropped at the museum’s entrance on Biscayne Boulevard. Give yourself about two hours for the contemporary collection, then spend a little time outside beneath the museum’s hanging gardens—the bay views are one of the best parts of the visit. The museum is generally open until early evening, but verify the current schedule and admission, usually around $16–18 for adults, before setting out.

Walk or take a short rideshare south to Bayside Marketplace, an easy first stop while you get your bearings. Browse the waterfront shops, listen to the live music, and choose something casual from the food hall or one of the outdoor counters; this is better for a relaxed snack or early meal than for a destination dining experience. The walk from Pérez Art Museum Miami takes around 15–20 minutes, though the route can feel hot in the afternoon, so rideshare is worthwhile if you have luggage or the sun is strong. Keep an eye on your belongings in the busy market area, particularly around the entrances and marina.

Evening — Classic South Beach Dinner

For dinner, take a rideshare from Bayside Marketplace to Joe’s Stone Crab in South Beach—normally 20–35 minutes, but allow longer during evening traffic. Joe’s Stone Crab is a Miami institution, and the atmosphere is lively rather than formal; arrive hungry for stone crab when in season, plus the fried chicken, hash browns, and key lime pie if you want the full classic order. Expect roughly $50–90 per person before drinks and tip. Reservations are strongly recommended, and stone crab availability varies by season, so check the menu ahead of time. After dinner, take a slow stroll around nearby South Beach before returning by rideshare; parking in this part of Miami is expensive and rarely worth the hassle on an arrival day.

Day 2 · Thu, Mar 26
Miami, FL

Miami neighborhoods

  1. Vizcaya Museum and Gardens — Coconut Grove; grand historic estate and formal gardens, morning (~2 hours).
  2. Coconut Grove — Coconut Grove; leafy streets, boutiques, and relaxed waterfront atmosphere, midday (~1.5 hours).
  3. Greenstreet Café — Coconut Grove; casual brunch or lunch, midday (~$15–30 per person).
  4. The Barnacle Historic State Park — Coconut Grove; glimpse of Miami’s pioneer-era waterfront homes, afternoon (~1 hour).

Morning — Vizcaya’s gardens

Start at Vizcaya Museum and Gardens when it opens, generally at 9:30 AM; check the official site before leaving because hours and timed-entry rules can change. From central Miami, a rideshare to 3251 South Miami Avenue usually takes 15–25 minutes. Allow about two hours for the Italianate villa, shaded terraces, and formal gardens overlooking Biscayne Bay. Admission is typically around $25 for adults, with reduced prices for children and seniors. The gardens are much more comfortable before the midday heat, so bring water, sunscreen, and shoes suitable for uneven paths.

Midday — Coconut Grove and lunch

Walk or take a short rideshare north into Coconut Grove, where the pace changes noticeably: leafy residential streets, independent boutiques, and outdoor cafés make this one of Miami’s best neighborhoods for an unhurried wander. Spend about 90 minutes around CocoWalk, Main Highway, and the quieter streets leading toward the water, but keep an eye on the weather—afternoon showers can arrive quickly. Have lunch at Greenstreet Café, a long-standing local favorite with a relaxed patio and generous brunch-style plates; budget roughly $15–30 per person, and expect a wait during the late-morning weekend rush. It is walkable from much of the Grove, though a rideshare is sensible if the heat is intense.

Afternoon — The Barnacle

Finish at The Barnacle Historic State Park, a short walk or five-minute rideshare from Greenstreet Café. The small waterfront property preserves one of Miami’s oldest surviving homes and offers a quieter, more intimate look at the city’s pioneer era than the grander morning estate. Plan on about an hour, including time beneath the mature trees and beside the bay. The park generally closes in the late afternoon, often around 5 PM, and admission is usually only a few dollars; confirm same-day hours before setting out. From there, return by rideshare to your hotel, or linger in Coconut Grove for a drink—the neighborhood is particularly pleasant around sunset.

Day 3 · Fri, Mar 27
Miami Beach, FL

Miami beaches

Getting there from Miami, FL
Rideshare (Uber/Lyft), 20–40 min, about $20–45. Depart after breakfast; traffic can be heavy. Book in the app.
  1. South Pointe Park — South Beach; scenic start beside the ocean and cruise channel, morning (~1 hour).
  2. Lummus Park — South Beach; classic beach time and Art Deco skyline views, late morning (~2 hours).
  3. The Betsy Hotel — Ocean Drive; elegant setting for a coffee break, afternoon (~1 hour; ~$10–20 per person).
  4. South Beach Room Escape — South Beach; indoor activity during the warmest part of the day, afternoon (~1.5 hours).
  5. Pubbelly Sushi — South Beach; creative dinner in a lively setting, evening (~$35–60 per person).

Morning — Oceanfront start

Begin at South Pointe Park around 8:30–9:00 AM, when the paths are cooler and quieter. Walk the promenade toward the tip of South Beach for views across the ocean, Fisher Island, and the cruise channel; the park and its outdoor areas are free, and an hour is plenty. From there, follow the beachfront north on foot—roughly 20–25 minutes—or take a quick rideshare if the heat is already building to Lummus Park. Settle in for a couple of hours between the palms and the sand, with the Ocean Drive Art Deco skyline just behind you. Beach access is free, but bring water, sunscreen, and a towel; chairs and umbrellas are available for hire along the shore, typically from around $20–40.

Afternoon — Ocean Drive and an indoor break

Walk west to The Betsy Hotel on Ocean Drive for a cooler pause and coffee in its polished lobby or veranda setting. Allow about an hour and expect roughly $10–20 per person; this is a good moment to escape the strongest midday sun rather than trying to fit in another beach stop. Afterward, continue into South Beach for South Beach Room Escape, allowing around 1½ hours. Reserve a session in advance, since afternoon slots can fill, and arrive 10–15 minutes early for check-in and briefing. The short walk between the hotel and the escape room should be manageable, though a rideshare is sensible if the weather is particularly hot.

Evening — Sushi in South Beach

Finish at Pubbelly Sushi, where inventive rolls and small plates make it easy to share dinner. It is a lively choice after the quieter morning, with a typical spend of about $35–60 per person before drinks and tip. Book ahead for an evening table, especially on a Friday, and plan on walking or using a short rideshare from the room-escape venue depending on the exact location. After dinner, take an unhurried stroll along Ocean Drive or the nearby residential streets before returning—South Beach is at its most atmospheric once the heat drops, but keep valuables tucked away in the busy nightlife areas.

Day 4 · Sat, Mar 28
Little Havana, Miami, FL

Miami cultural district

Getting there from Miami Beach, FL
Rideshare (Uber/Lyft), 20–35 min, about $15–30. Leave in the morning before peak traffic.
  1. Máximo Gómez Park — Little Havana; watch domino players and absorb neighborhood life, morning (~45 minutes).
  2. Calle Ocho Walk of Fame — Little Havana; explore Cuban-American landmarks and murals, morning (~1 hour).
  3. Ball & Chain — Little Havana; historic club for live music and lunch, midday (~1.5 hours; ~$25–50 per person).
  4. Cuban Memorial Boulevard — Little Havana; reflective visit to important exile-history monuments, afternoon (~1 hour).
  5. Cubaocho Museum & Performing Arts Center — Little Havana; Cuban art and music in a distinctive gallery-bar setting, evening (~1.5 hours).

Morning — Little Havana’s neighborhood rhythm

Start at Máximo Gómez Park, known locally as Domino Park, around 9:00 AM. It is free and usually liveliest later in the morning, when regulars gather around the domino tables; watch quietly from the edge and take in the lively Spanish-language chatter. From there, stroll west along Calle Ocho, pausing for the painted storefronts, Cuban-American memorials, and the Calle Ocho Walk of Fame. Allow about an hour, with time for a cafecito or pastelito from a small ventanita along the way; most cafés open early, but exact hours vary.

Midday — Music and lunch on Calle Ocho

Continue on foot to Ball & Chain, the famous club at the corner of Southwest Eighth Street and Southwest 15th Avenue. It is worth checking the day’s music schedule before setting out, as live performances often begin around lunchtime and the room can fill quickly. Settle in for about 90 minutes over Cuban-inspired food and drinks—budget roughly $25–50 per person before an enthusiastic tip. This is a good place to slow down rather than rush through lunch; the interior and small stage carry much of the neighborhood’s old nightlife character.

Afternoon and evening — Memory, art, and music

After lunch, walk or take a short rideshare—around five minutes—to Cuban Memorial Boulevard, where the monuments and memorials offer a quieter, more reflective look at the history of Cuban exile. Give yourself about an hour, especially if you want to read the inscriptions and walk between the memorial sites. In the early evening, continue to Cubaocho Museum & Performing Arts Center, generally opening in the afternoon and running into the night; verify current hours and any performance charge before visiting. Allow 90 minutes to browse the Cuban art collection and stay for music in its distinctive gallery-bar setting. Rideshares are easiest here, particularly after dark; expect roughly $15–30 back to Miami Beach, depending on traffic and surge pricing.

Day 5 · Sun, Mar 29
Key Largo, FL

Florida Keys gateway

Getting there from Little Havana, Miami, FL
Rental car via US-1/Overseas Highway, 1.5–2 hr, approximately $45–90/day plus fuel. Depart around 9:00 AM; reserve through Rentalcars.com, Discover Cars, or directly with the provider.
  1. Drive from Miami to Key Largo via US-1 — Miami–Key Largo; allow ~1.5–2 hours, depart around 9:00 AM; use reserved lodging parking after arrival.
  2. John Pennekamp Coral Reef State Park — Key Largo; glass-bottom viewing, beaches, and mangrove scenery, late morning (~2.5 hours).
  3. Mrs. Mac’s Kitchen — Key Largo; classic Keys lunch, midday (~$15–30 per person).
  4. Florida Keys Wild Bird Center — Tavernier; see rescued birds and walk the short shoreline trail, afternoon (~1 hour).
  5. Key Largo Hammock Botanical State Park — Key Largo; quiet tropical forest walk, late afternoon (~1.5 hours).

Morning — Down the Overseas Highway

Pick up your rental car in Miami and leave Little Havana around 9:00 AM for Key Largo via US-1, allowing about 1½–2 hours. Traffic can be slow through southern Miami and Homestead, so have coffee and water in the car and keep some flexibility for roadside stops. Once you arrive, leave the car at your lodging if possible; parking is much easier there than trying to carry luggage between attractions.

Head first to John Pennekamp Coral Reef State Park, where the late-morning glass-bottom boat outing is the best fit for a first introduction to the Keys. Boat trips generally last around 2–2½ hours, and reservations are strongly advised, particularly during spring travel season; check-in is usually required well before departure. If boat availability is limited, use the park’s beach and short nature trails instead. Park admission is charged per vehicle, while boat trips cost extra—bring sunscreen, a hat, and a light layer because the boat can be breezy.

Lunch — A proper Keys classic

Drive a few minutes to Mrs. Mac’s Kitchen for lunch, allowing roughly $15–30 per person. This is a casual, popular spot rather than a polished waterfront restaurant, with generous seafood, sandwiches, and the sort of old-school Keys atmosphere that suits the day. Expect a possible wait at peak lunchtime; if you are on a boat schedule, arrive closer to 12:30 PM than noon. Afterward, continue north on US-1 for about 10–15 minutes to Florida Keys Wild Bird Center in Tavernier. The rescued-bird enclosures and short shoreline trail take about an hour, and the visit is especially pleasant in the afternoon when you can slow down and look across the mangroves.

Late Afternoon — Hammock forest

Return south toward Key Largo for Key Largo Hammock Botanical State Park, leaving at least 1½ hours for its quiet tropical-forest trails. This is a low-key contrast to the water activities: expect shade, tangled vegetation, and the chance to spot small birds and lizards rather than a dramatic landmark. Wear closed shoes and repellent, and check the park’s current access and trail conditions before setting out, as facilities can be limited. Finish back at your lodging around sunset, then keep the evening easy—this is a good night for a nearby seafood dinner and an early start tomorrow rather than another long drive.

Day 6 · Mon, Mar 30
Key Largo, FL

Key Largo

  1. Rainbow Reef Dive Center — Key Largo; snorkeling or diving on nearby reefs, morning (~3 hours; advance booking essential).
  2. Harriette’s Restaurant — Key Largo; popular breakfast or lunch stop, midday (~$10–25 per person).
  3. Dagny Johnson Key Largo Hammock Botanical State Park — Key Largo; explore hardwood hammock trails, afternoon (~1.5 hours).
  4. The African Queen — Key Largo; see the historic film boat and waterfront, late afternoon (~45 minutes).
  5. Snook’s Bayside Restaurant & Grand Tiki — Key Largo; sunset dinner over Florida Bay, evening (~$30–60 per person).

Morning — Reef time

Book a morning trip with Rainbow Reef Dive Center in advance; snorkeling and dive departures fill quickly, especially in late March. Arrive 30–45 minutes before the boat leaves for check-in, waivers, equipment fitting, and parking. The reef outing generally takes about three hours, including the ride offshore, and conditions are usually best earlier in the day. Bring reef-safe sunscreen, a towel, water, and a light layer for the boat ride; seas can feel surprisingly cool even in Florida sunshine. Expect roughly $75–150 for snorkeling or considerably more for a two-tank dive, depending on equipment and certification requirements.

Midday — A relaxed Keys lunch

After returning, have lunch at Harriette’s Restaurant, a cheerful, unfussy stop on Overseas Highway. It is well suited to a post-boat appetite, with breakfast plates, sandwiches, and salads generally running $10–25 per person. Allow a little extra time if there is a queue, and keep the rest of the afternoon loose rather than trying to fit in another water activity. From the dive center, the restaurant is only a short drive along US-1; parking is straightforward but can become busy around the late-morning breakfast rush.

Afternoon — Hammock trails and a piece of film history

Drive north through Key Largo to Dagny Johnson Key Largo Hammock Botanical State Park, about 15–20 minutes depending on your starting point. Pay the modest day-use fee at the entrance and spend around 1½ hours on the shaded hardwood-hammock trails. This is a good counterpoint to the open water: look for tropical plants, small lizards, and birds in the dense greenery, and bring insect repellent and water. Continue south afterward to The African Queen, where the historic vessel from the classic film is moored beside the waterfront. A visit takes about 45 minutes; check the current viewing or tour schedule before going, since access can vary and the boat is best appreciated with a little daylight.

Evening — Sunset over Florida Bay

Finish at Snook’s Bayside Restaurant & Grand Tiki, arriving 30–45 minutes before sunset if you want a waterside table. The setting faces Florida Bay, and the outdoor seating is the reason to come: settle in for seafood, salads, and tropical drinks while the light fades across the water. Dinner is typically about $30–60 per person before drinks and tip. It is a short drive from The African Queen, but use a rideshare if you plan to drink; Key Largo is spread along US-1, and evening service can be limited, so arrange the return ride before the sun goes down.

Day 7 · Tue, Mar 31
Islamorada, FL

Islamorada

Getting there from Key Largo, FL
Rental car via US-1, 30–40 min, about $5–10 in fuel. Leave early enough for the morning Windley Key stop.
  1. Windley Key Fossil Reef Geological State Park — Islamorada; walk former quarry trails through ancient coral, morning (~1.5 hours).
  2. Islamorada Fish Company — Islamorada; casual seafood lunch beside the water (~$20–40 per person).
  3. Theater of the Sea — Islamorada; marine-life presentations and lagoon habitats, afternoon (~2.5 hours).
  4. Robbie’s of Islamorada — Islamorada; feed tarpon and browse the waterfront market, late afternoon (~1.5 hours).
  5. Morada Bay Beach Café — Islamorada; relaxed sunset meal on the bay, evening (~$30–60 per person).

Morning — Ancient coral at Windley Key Fossil Reef Geological State Park

Leave Key Largo early enough to reach Windley Key Fossil Reef Geological State Park around opening time, when the former quarry trails are cooler and quieter. Allow about 30–40 minutes along US-1, then follow the signs to the park entrance; parking is limited but usually manageable in the morning. The short trails wind through exposed fossilized coral, with interpretive signs explaining how the Keys were formed. Plan on roughly 1½ hours, wearing proper shoes and bringing water—there is little shade. Check the Florida State Parks website for current hours and admission, generally a modest day-use fee.

Lunch — Waterfront seafood

Drive a few minutes back along US-1 to Islamorada Fish Company, a relaxed place for a seafood lunch beside the water. Expect about $20–40 per person; fish sandwiches, fried seafood, and grilled options are easy choices after the quarry walk. Sit outside if the breeze is comfortable, but keep an eye on the time: lunch can become leisurely here. From the restaurant, it is only a short drive to Theater of the Sea, so there is no need to move the car far or rush through the meal.

Afternoon — Marine life and the harbor

Spend around 2½ hours at Theater of the Sea, whose lagoon habitats and scheduled presentations make it one of the more approachable wildlife stops in the Upper Keys. Look up the day’s showtimes before arriving and work backward from the presentations you most want to see; the dolphin and sea-lion programs are popular. Admission is typically in the $40–60 range for adults, with discounts sometimes available online. Afterward, continue south on US-1 for about 10 minutes to Robbie’s of Islamorada. The tarpon-feeding platform, small waterfront market, and harbor views are best enjoyed without over-planning; the feeding area has a small separate fee, and the dock can be hot and slippery.

Evening — Sunset at Morada Bay Beach Café

Finish at Morada Bay Beach Café, a short drive farther south, for a relaxed dinner facing Florida Bay. Arrive before sunset if you want a table close to the sand—this is one of the best places in Islamorada to let the evening unfold rather than squeeze in another attraction. Budget roughly $30–60 per person, more if you add cocktails or several seafood dishes. The restaurant’s hours and seating arrangements can vary, so check ahead and make a reservation if available; after dark, US-1 is easy to drive but poorly suited to casual roadside stopping, so arrange your return to the hotel before dinner.

Day 8 · Wed, Apr 1
Marathon, FL

Marathon

Getting there from Islamorada, FL
Rental car via US-1, 1–1.25 hr, about $8–15 in fuel. Depart around 9:00 AM; stop at the History of Diving Museum first if desired.
  1. Drive from Islamorada to Marathon via US-1 — Upper Keys–Marathon; allow ~1 hour, depart around 9:00 AM.
  2. History of Diving Museum — Islamorada; optional final Upper Keys stop before continuing south, morning (~1 hour).
  3. The Turtle Hospital — Marathon; learn about sea-turtle rescue and rehabilitation, early afternoon (~1.5 hours; reserve ahead).
  4. Keys Fisheries — Marathon; waterfront seafood lunch, midday (~$20–40 per person).
  5. Sombrero Beach — Marathon; swim or relax on one of the area’s best public beaches, afternoon (~2 hours).
  6. Old Seven Mile Bridge — Marathon; sunset walk with expansive Gulf views, evening (~1 hour).

Morning — Final Upper Keys stop and the drive south

If you would like one last stop before leaving Islamorada, visit the History of Diving Museum for about an hour. It usually opens at 10:00 AM; check the official schedule before setting out, as hours can vary seasonally. The collection is wonderfully eccentric, with antique diving helmets, underwater cameras, and stories from the early days of exploration. Afterward, continue south on US-1 toward Marathon—the drive is roughly an hour, with the highway narrowing into a scenic chain of bridges and small islands. Keep the car fueled and allow extra time for photo pull-offs, but avoid stopping on the bridge shoulders.

Midday and Afternoon — Turtle rescue and a waterfront lunch

Aim for an early-afternoon visit to The Turtle Hospital in Marathon, reserving ahead because guided tours commonly sell out. The visit takes around 90 minutes and explains the rescue, treatment, and release of injured sea turtles; arrive a little early for check-in and parking. From there, drive a few minutes to Keys Fisheries, a casual waterfront spot where you can order fresh seafood and eat with views over the working harbor. Plan on roughly $20–40 per person, and expect a relaxed, counter-service atmosphere rather than a quick roadside stop.

After lunch, drive about 10 minutes to Sombrero Beach, one of Marathon’s best public beaches. Spend the afternoon swimming, walking the shoreline, or simply settling under the palms; parking is free but can fill on warm weekends, so arriving earlier helps. Bring water, sunscreen, and something to sit on—shade is limited, and the Keys sun is deceptively strong even when a breeze is blowing.

Evening — Sunset on the old bridge

Finish at Old Seven Mile Bridge, reached by driving west along US-1 and following signs for the historic bridge access. The preserved bridge is closed to vehicle traffic, making it ideal for a slow sunset walk with broad Gulf views. Allow about an hour, and bring a light layer because the bridge can feel breezy after sunset. The access area has limited facilities and parking, so arrive before the sky changes color; this is a particularly good place to watch the lower sun turn the water copper without the busier feel of a formal attraction.

Day 9 · Thu, Apr 2
Key West, FL

Key West arrival

Getting there from Marathon, FL
Rental car via US-1, 1.5–2 hr, about $10–20 in fuel. Depart around 9:00 AM and reserve lodging or downtown parking in advance.
  1. Drive from Marathon to Key West via US-1 — Lower Keys–Key West; allow ~1.5–2 hours, depart around 9:00 AM; park at your lodging or a downtown garage.
  2. Fort Zachary Taylor Historic State Park — Key West; combine Civil War history with a beautiful beach, late morning (~2 hours).
  3. Blue Heaven — Bahama Village; atmospheric lunch in a landmark courtyard, midday (~$25–50 per person).
  4. Key West Butterfly and Nature Conservatory — Old Town; colorful indoor garden with free-flying butterflies, afternoon (~1 hour).
  5. Mallory Square — Waterfront; join the famous sunset celebration, evening (~1.5 hours).
  6. Garbo’s Grill — Truman Waterfront area; casual seafood or taco dinner (~$15–30 per person).

Morning — Arrive in Key West and settle in

Leave Marathon around 9:00 AM for Key West via US-1; the drive is usually 1½–2 hours, with the Lower Keys bridges and narrow stretches making it slower than the distance suggests. Have your lodging address ready and confirm parking before arrival—many Old Town properties have limited spaces, while the Old Town Parking Garage on Grinnell Street is a practical fallback. Once you have dropped your bags, drive or take a short rideshare to Fort Zachary Taylor Historic State Park. The park generally opens at 8:00 AM and charges an entrance fee of roughly $6 per vehicle, with additional fees possible for larger groups. Allow about two hours to walk around the Civil War fort, browse the shaded paths, and swim or relax on the beach; bring water shoes, as parts of the shoreline are rocky.

Lunch and Afternoon — Bahama Village to Old Town

From Fort Zachary Taylor, it is about a 10-minute drive or a 20-minute walk into Bahama Village for lunch at Blue Heaven. The courtyard is one of Key West’s most atmospheric dining spots, with tropical foliage, live music, and the resident chickens wandering through the tables. Brunch and lunch can be busy, so expect a wait and keep the order relaxed; budget approximately $25–50 per person before drinks and tip. After lunch, walk north through Bahama Village and along nearby Old Town streets to the Key West Butterfly and Nature Conservatory on Duval Street. Plan about an hour inside the warm, lush conservatory, where butterflies and small birds move freely; admission is generally around $18–25 for adults, and the last entry is usually well before closing, so check the day’s hours before setting out.

Evening — Sunset at the waterfront and dinner

Head toward Mallory Square by around 5:00 PM, allowing time to browse the waterfront and find a viewing spot before the sunset crowds gather. The celebration is free, though the square becomes especially busy in the final hour; street performers, musicians, and artists usually begin building the atmosphere well before sunset. Afterward, walk or take a short rideshare toward the Truman Waterfront area for dinner at Garbo’s Grill, a casual food truck known for seafood, tacos, and generous portions. Expect roughly $15–30 per person, with limited outdoor seating and a queue at peak dinner time. It is a good first evening in Key West to keep unhurried—sunset and dinner are close enough together that you can simply wander between them rather than trying to fit in another major sight.

Day 10 · Fri, Apr 3
Key West, FL

Key West historic district

  1. Ernest Hemingway Home and Museum — Old Town; tour the author’s home and meet its famous cats, morning (~1.5 hours).
  2. Key West Lighthouse — Old Town; climb for panoramic views, late morning (~1 hour).
  3. Kermit’s Key West Key Lime Shoppe — Old Town; key-lime pie break, midday (~30 minutes; ~$8–15 per person).
  4. Harry S. Truman Little White House — Old Town; explore presidential history in an authentic residence, afternoon (~1.5 hours).
  5. The Stoned Crab — Stock Island; sustainable seafood dinner away from crowded Old Town, evening (~$35–70 per person).

Morning — Ernest Hemingway Home and Museum

Start around 9:00 AM at the Ernest Hemingway Home and Museum on Whitehead Street, before Old Town’s lanes become busy and hot. The guided visit usually takes about 1½ hours and covers the author’s rooms, garden, and writing life; the resident six-toed cats are part of the experience. Admission is generally around $18–20 per adult, and the property typically opens at 9:00 AM, though confirm the current schedule before going. Walk here if you are staying in Old Town; otherwise, use a rideshare, since parking nearby is limited and often expensive.

Late Morning and Lunch — Key West Lighthouse and Kermit’s Key West Key Lime Shoppe

Cross Whitehead Street to the Key West Lighthouse, where the 88-step climb rewards you with a broad view over the rooftops, harbor, and surrounding island. Allow about an hour, including the small keeper’s-quarters museum; admission is usually roughly $17–20. Afterward, stroll toward Kermit’s Key West Key Lime Shoppe for a cool slice of key-lime pie or a chocolate-dipped frozen bar. Budget about $8–15 per person. This is a snack rather than a full lunch, so add a simple sandwich or salad nearby if needed, but keep the pace relaxed—Old Town is best enjoyed by wandering shaded side streets rather than rushing between sights.

Afternoon — Harry S. Truman Little White House

Spend the afternoon at the Harry S. Truman Little White House, a short walk away on Front Street. The guided tour takes about 1½ hours and gives useful context on Truman’s time in Key West, with the preserved house and furnishings making it feel more intimate than a conventional museum. Admission is generally around $25–30, and tours run throughout the day; check availability online, particularly during busy spring weeks. Leave some time afterward to browse the quieter streets around Simonton Street and the waterfront before heading out of the historic core.

Evening — The Stoned Crab

For dinner, take a rideshare to The Stoned Crab on Stock Island, roughly 10–15 minutes from Old Town depending on traffic. It is a good change of scene: less touristy than Duval Street, with a casual marina setting and a menu focused on Florida seafood and sustainable local catches. Expect approximately $35–70 per person before drinks and tip, and reserve ahead if you want a table at a popular dinner hour. A rideshare is preferable to driving, as parking is easier than in Old Town but still limited during the evening.

Day 11 · Sat, Apr 4
Key West, FL

Key West neighborhoods

  1. Key West Garden Club at West Martello — Whitehead Street; free gardens inside a historic fort, morning (~1 hour).
  2. Key West Cemetery — Old Town; discover distinctive local history and above-ground graves, late morning (~1 hour).
  3. Santiago’s Bodega — Old Town; tapas-style lunch, midday (~$25–45 per person).
  4. Custom House Museum — Old Town; compact museum covering Key West’s maritime and civic history, afternoon (~1.5 hours).
  5. Sunset sail from Key West Bight — Historic Seaport; enjoy the island from the water, late afternoon/evening (~2 hours).

Morning — Key West Garden Club at West Martello

Start around 9:00 AM at the Key West Garden Club at West Martello, on Whitehead Street beside the Atlantic. The gardens are free, though donations are appreciated, and an hour is enough to wander through the former Civil War fort’s courtyards, arches, orchids, palms, and shaded paths. It is a particularly good first stop before the day becomes hotter. From most Old Town hotels, walk if you are nearby; otherwise, a short bicycle ride or rideshare is easier than trying to find parking around the fort.

Continue north into Old Town to Key West Cemetery, allowing about 15–20 minutes on foot or a few minutes by bike. Spend roughly an hour looking at the above-ground tombs and distinctive local memorials, including the island’s famously irreverent epitaphs. Keep voices low and remain on the paths—the cemetery is still an active, locally used burial ground. There is no admission charge, but a small donation helps with maintenance.

Lunch and Afternoon — Old Town history

Have lunch at Santiago’s Bodega, a relaxed tapas restaurant on Simonton Street. Plan on $25–45 per person depending on how many plates and drinks you share; ordering several dishes for the table works well. A midday meal here gives you time to sit down properly rather than grazing in the heat, but check the current opening time and reserve if possible, as the small dining room can fill quickly.

After lunch, walk toward the waterfront for the Custom House Museum in the Key West Historic Seaport. Allow about 1½ hours for its maritime, shipwreck, immigration, and civic-history displays. The museum is compact and air-conditioned, making it a useful break during the hottest part of the afternoon; admission is typically in the mid-teens, with discounts sometimes available. You will be close to Key West Bight, so avoid moving the car—Old Town is much easier on foot, and downtown parking is limited and expensive.

Evening — Sunset from the water

Finish with your reserved sunset sail from Key West Bight, generally departing in the late afternoon and lasting about two hours. Arrive 30–45 minutes early at the operator’s check-in point in the Historic Seaport, since dock locations vary and boarding can be brisk. Bring a light layer, sunscreen, and cash for gratuity; the breeze feels noticeably cooler offshore. The sunset is the main event, but the slow view back toward Old Town, the lighthouse area, and the Lower Keys is often the best part. After returning, stay around the Bight for dinner or walk back through Old Town—no further sightseeing is necessary tonight.

Day 12 · Sun, Apr 5
Fort Myers, FL

Return to mainland Florida

Getting there from Key West, FL
Rental car via US-1, then US-41/Tamiami Trail, 5.5–6.5 hr, about $35–60 in fuel. Depart around 7:30 AM; allow for breaks and possible traffic. Book via Rentalcars.com, Discover Cars, or the rental company.
  1. Drive from Key West to Fort Myers via US-1 and US-41 — Keys–Southwest Florida; allow ~5.5–6.5 hours, depart around 7:30 AM; plan fuel and rest stops, then use hotel parking.
  2. Robert Is Here Fruit Stand — Homestead; quick tropical-fruit stop near the mainland route, morning (~30 minutes).
  3. Miccosukee Restaurant — Tamiami Trail; convenient Everglades-area lunch stop (~$15–30 per person).
  4. Six Mile Cypress Slough Preserve — Fort Myers; stretch your legs on an elevated wetland boardwalk, late afternoon (~1.5 hours).
  5. Ford’s Garage — Fort Myers River District; relaxed burger-and-beer dinner (~$20–35 per person).

Morning — Across the Keys and a tropical stop

Leave Key West around 7:30 AM for the long drive north on US-1, allowing 5½–6½ hours overall to Fort Myers. This is a scenic but tiring travel day, so fill the tank before leaving and keep water and snacks in the car; services become more spread out once you are beyond the populated Keys. Near Homestead, stop at Robert Is Here Fruit Stand for about 30 minutes. It is an easy break near the mainland route, with fresh tropical fruit, smoothies, and local specialties—try something seasonal such as mango, guava, or mamey. Check opening hours before departure, as they can change outside peak season.

Lunch — Tamiami Trail

Continue west along US-41, the Tamiami Trail, and stop at Miccosukee Restaurant around lunchtime. Expect roughly $15–30 per person for a casual meal, with regional and Native-inspired dishes that make a more interesting break than standard highway food. Give yourself a little flexibility here: traffic, construction, and slow-moving vehicles on the two-lane stretches can easily add time. After lunch, continue toward Fort Myers, arriving in the mid- to late afternoon; check into your hotel and use its parking rather than trying to move the car immediately.

Late Afternoon — Cypress and sunset air

Once settled, drive to Six Mile Cypress Slough Preserve for an easy first look at the Southwest Florida landscape. The elevated boardwalk takes about 1½ hours and passes through cypress wetland, with opportunities to spot turtles, wading birds, and perhaps an alligator in the shaded water. The preserve generally closes before dark, so verify the day’s closing time and arrive with enough daylight; comfortable shoes, insect repellent, and water are worthwhile. Afterward, return to the Fort Myers River District for dinner at Ford’s Garage, a relaxed spot for burgers, sandwiches, and beer at about $20–35 per person. It is a good low-effort finish after the drive, and you can walk around the nearby historic streets afterward if you still have energy.

Day 13 · Mon, Apr 6
Fort Myers, FL

Fort Myers

  1. Edison and Ford Winter Estates — Downtown Fort Myers; tour historic homes, gardens, and laboratories, morning (~3 hours).
  2. The Standard Restaurant — Downtown; polished lunch in a historic district setting (~$25–50 per person).
  3. Burroughs Home & Gardens — Downtown riverfront; visit a preserved early-Fort Myers mansion, afternoon (~1 hour).
  4. Fort Myers River District — Downtown; browse galleries, shops, and public art, late afternoon (~1.5 hours).
  5. Luminary Hotel rooftop — Downtown; sunset drinks and skyline views, evening (~$15–30 per person).

Morning — Edison and Ford Winter Estates

Start around 9:00 AM at Edison and Ford Winter Estates on McGregor Boulevard, one of Fort Myers’s essential visits and an easy way to understand the city’s early-20th-century character. Allow roughly three hours for the historic homes, laboratories, museum exhibits, and botanical gardens; the riverside grounds are particularly pleasant before the afternoon heat builds. Admission is typically around $25–35 for adults, with occasional changes by season, so check the official website before going. Wear comfortable shoes and bring water—the gardens are more spread out than they first appear.

Lunch and Afternoon — Downtown’s historic riverfront

Walk or take a short rideshare into the Fort Myers River District for lunch at The Standard Restaurant, a polished but relaxed choice in a handsome historic setting. Expect about $25–50 per person before drinks; reservations are sensible if you want a table at peak lunchtime. Afterward, visit Burroughs Home & Gardens, a preserved 1901 mansion on the riverfront. Guided tours generally take about an hour and operate on a limited schedule, so confirm the day’s tour times in advance; arrive a few minutes early rather than assuming you can join at any point.

Spend the late afternoon wandering the Fort Myers River District, where First Street, Hendry Street, and the surrounding side streets are lined with small galleries, boutiques, cafés, and public art. This is best treated as unstructured time rather than a checklist: browse the historic storefronts, pause in a shaded pocket park, and look for the district’s murals and sculptures. Most shops keep daytime hours and begin closing around 5:00 or 6:00 PM, while parking garages and metered spaces make it easier to leave the car parked for the whole afternoon.

Evening — Rooftop sunset at Luminary Hotel

Finish at the rooftop of Luminary Hotel & Co., where you can settle in for sunset drinks and broad views over the Caloosahatchee River and downtown rooftops. Drinks usually run about $15–30 per person, and arriving 30–45 minutes before sunset gives you the best chance of a comfortable table without rushing. Dress neatly but casually, and check the rooftop’s current hours or reservation policy before heading over, since weather and private events can affect access. From the River District, it is an easy walk; otherwise, use a short rideshare if the heat has taken its toll.

Day 14 · Tue, Apr 7
Sanibel, FL

Sanibel Island

Getting there from Fort Myers, FL
Rental car via McGregor Boulevard and the Sanibel Causeway, 45–60 min, about $5–10 in fuel plus any applicable causeway fees. Depart around 8:00 AM for refuge parking.
  1. Drive from Fort Myers to Sanibel Island — Fort Myers–Sanibel; allow ~45–60 minutes, depart around 8:00 AM; arrive early for parking.
  2. J.N. “Ding” Darling National Wildlife Refuge — Sanibel; look for birds and wildlife along the refuge drive, morning (~2 hours).
  3. The Island Cow — Sanibel; casual island lunch, midday (~$20–35 per person).
  4. Sanibel Historical Museum and Village — Sanibel; learn about early island life, afternoon (~1 hour).
  5. Bowman’s Beach — Sanibel; shelling and a peaceful Gulf sunset, late afternoon (~2 hours).

Morning — J.N. “Ding” Darling National Wildlife Refuge

Leave Fort Myers around 8:00 AM and allow roughly 45–60 minutes to reach Sanibel Island via McGregor Boulevard and the Sanibel Causeway. The refuge is best tackled early, before the heat builds and parking fills. At J.N. “Ding” Darling National Wildlife Refuge, take the Wildlife Drive if open—usually a slow, one-way route of about four miles—and allow around two hours for frequent stops. Bring binoculars, water, sunscreen, and insect repellent; roseate spoonbills, herons, egrets, ospreys, and alligators are possible sightings. Check the official refuge schedule before leaving, as the drive typically closes one day each week and entrance fees or vehicle passes may apply.

Lunch — The Island Cow

Drive about 15 minutes east across Sanibel to The Island Cow, a relaxed, colorful choice for lunch on Periwinkle Way. Expect generous seafood, sandwiches, salads, and island-style comfort food at roughly $20–35 per person. It is popular, so arriving slightly before noon helps avoid a wait; otherwise, settle in for the unhurried pace Sanibel does well.

Afternoon — Sanibel Historical Museum and Village

After lunch, walk or drive a few minutes to the Sanibel Historical Museum and Village, where a collection of preserved island buildings explains Sanibel’s farming, fishing, and early settlement history. Allow about an hour and check the current opening days and hours before visiting, since this small volunteer-supported museum often operates on a limited seasonal schedule. From here, continue west on Periwinkle Way and Sanibel-Captiva Road toward Bowman’s Beach, roughly 15–20 minutes by car.

Late afternoon — Bowman’s Beach

Spend the rest of the day at Bowman’s Beach, one of Sanibel’s quieter Gulf beaches and a good place for shelling. The walk from the parking area to the sand is longer than at many beach access points, so carry water and keep valuables out of the car. Parking is paid and can fill by late afternoon; arrive with some flexibility, especially during spring travel season. Wander the shoreline, look for intact shells without taking live ones, and stay for the sunset over the Gulf. Sanibel’s beaches are protected nesting and wildlife habitat, so follow posted access rules and leave the shore as you found it.

Day 15 · Wed, Apr 8
Naples, FL

Naples

Getting there from Sanibel, FL
Rental car via FL-867 and I-75, 1.25–1.5 hr, about $10–18 in fuel. Depart around 8:30 AM.
  1. Drive from Sanibel to Naples — Sanibel–Naples; allow ~1.25–1.5 hours, depart around 8:30 AM.
  2. Naples Botanical Garden — East Naples; lush tropical landscapes and water gardens, late morning (~2.5 hours).
  3. The French Brasserie Rustique — Bayshore Arts District; refined French lunch (~$30–60 per person).
  4. Tin City Waterfront Shops — Downtown Naples; browse waterfront stores and galleries, afternoon (~1.5 hours).
  5. Naples Pier — Old Naples; classic Gulf views and sunset atmosphere, evening (~1 hour).

Morning — From Sanibel to Naples Botanical Garden

Leave Sanibel Island around 8:30 AM for Naples, allowing roughly 1¼–1½ hours via FL-867 and I-75. After crossing back over the causeway, follow the signs toward East Naples; the garden has on-site parking, but arriving before late morning makes the visit more comfortable. Spend about 2½ hours at Naples Botanical Garden, wandering through its tropical landscapes, water gardens, and quiet paths. Check the official schedule before leaving—hours and admission can change seasonally, with general admission typically around $25–30 for adults.

Lunch — The French Brasserie Rustique

Drive about 10–15 minutes to the Bayshore Arts District for lunch at The French Brasserie Rustique. This is a good place to slow the pace after the garden: expect classic French dishes, polished service, and roughly $30–60 per person before drinks and gratuity. A reservation is sensible, particularly around the weekend, and allow about 1¼ hours rather than trying to rush through the meal.

Afternoon — Tin City Waterfront Shops

From the restaurant, it is roughly a 10-minute drive to Tin City Waterfront Shops in downtown Naples. Browse the small waterfront stores, galleries, and local gift shops at an easy pace for about 1½ hours; there are cafés and places to pause along the water if the afternoon is warm. Parking is available nearby, though spaces can fill, so use the lot rather than circling downtown streets. Keep the rest of the afternoon flexible—Naples is pleasant to explore slowly, especially around the nearby historic center.

Evening — Naples Pier

Finish at Naples Pier in Old Naples, about a 10-minute drive from Tin City. Go around an hour before sunset for the classic Gulf view, a walk over the water, and the chance to see local anglers at work; the pier itself is free, although parking near the beach may be metered or limited. Sunset times in April are around 7:50 PM, but check the forecast and arrive early for a space. Afterward, walk a little along the residential streets of Old Naples or return to your accommodation for dinner rather than adding another major stop.

Day 16 · Thu, Apr 9
Naples, FL

Naples coast

  1. Delnor-Wiggins Pass State Park — North Naples; excellent beach time and clear Gulf water, morning (~2.5 hours).
  2. The Village Shops on Venetian Bay — Park Shore; waterside shopping and a break, midday (~1 hour).
  3. USS Nemo Restaurant — Park Shore; polished seafood lunch or early dinner (~$40–75 per person).
  4. Corkscrew Swamp Sanctuary — East Naples; walk the famous cypress-boardwalk ecosystem, afternoon (~2 hours).
  5. Celebration Park — North Naples; food-truck-style waterfront dinner setting, evening (~$20–40 per person).

Morning — Delnor-Wiggins Pass State Park

Start early at Delnor-Wiggins Pass State Park, ideally arriving around 8:00 AM before the Gulf beach parking fills. The entrance is off 111th Avenue North in North Naples, roughly 20–30 minutes from central Naples; the park charges a vehicle admission fee, commonly around $6–8, though availability and rates can change. Spend about 2½ hours on the sand and in the usually clear, shallow Gulf water, and bring reef-safe sunscreen, drinking water, and something for shade. This is one of the area’s best beach stops, but it has limited facilities and can close to incoming cars once full, so an early start matters.

Midday — The Village Shops on Venetian Bay and lunch

Drive south along Gulf Shore Drive toward The Village Shops on Venetian Bay, allowing about 15–20 minutes. It is a pleasant place for a slower midday wander: browse the small boutiques, sit beside the water, and take a break from the sun for about an hour. For lunch, settle at USS Nemo Restaurant, a polished local seafood favorite in Park Shore, rather than rushing straight into the afternoon. Expect roughly $40–75 per person before drinks and tip; reservations are sensible, particularly during the busy winter season. Dress resort-casual, and allow extra time if you choose a seafood special or a full sit-down meal.

Afternoon — Corkscrew Swamp Sanctuary

After lunch, drive east to Corkscrew Swamp Sanctuary, usually 35–45 minutes depending on traffic. The entrance and visitor center are on Immokalee Road, well outside the beach district, and admission is generally in the $15–20 range for adults. Follow the roughly 2¼-mile elevated boardwalk through pine flatwoods, wet prairie, and old-growth bald-cypress forest; two hours gives you time to stop for wading birds, alligators, and the changing vegetation without hurrying. Check the sanctuary’s same-day closing time before leaving, since it can vary seasonally, and bring insect repellent, water, and a hat—the boardwalk is shaded in sections but exposed in others.

Evening — Celebration Park

Finish at Celebration Park in North Naples, returning west for a relaxed waterfront dinner among food-truck-style vendors. It is a casual contrast to USS Nemo Restaurant, with outdoor seating, drinks, and rotating menus; budget about $20–40 per person. Go around 6:00 PM for the most comfortable light and a chance to eat without a long wait, then linger by the water rather than trying to add another formal attraction. Parking can be busy at dinner, so arrive with a little patience and expect the evening to feel more social and informal than the rest of the day.

Day 17 · Fri, Apr 10
Sarasota, FL

Sarasota arrival

Getting there from Naples, FL
Rental car via I-75, 1.5–2 hr, about $12–22 in fuel. Depart around 9:00 AM.
  1. Drive from Naples to Sarasota via I-75 — Southwest Gulf Coast; allow ~1.5–2 hours, depart around 9:00 AM.
  2. Mote SEA Aquarium — Sarasota; explore marine science exhibits on the downtown waterfront, late morning (~2 hours).
  3. Columbia Restaurant — St. Armands Circle; historic Spanish-Cuban lunch (~25–50 per person).
  4. St. Armands Circle — Lido Key; browse shops and public art, afternoon (~1.5 hours).
  5. Lido Beach — Lido Key; unwind by the Gulf before dinner, late afternoon (~1.5 hours).

Morning — Arrive in Sarasota and visit Mote SEA Aquarium

Leave Naples around 9:00 AM for Sarasota via I-75, allowing roughly 1½–2 hours, plus time for traffic around the exits. Go straight to Mote SEA Aquarium on Ken Thompson Parkway; parking is available on-site, though the lot can fill during school holidays. Allow about two hours for the aquariums and marine-science exhibits, and check the official opening time and ticket availability before leaving—timed entry or advance booking may apply. The aquarium is a good first stop after the drive, with enough indoor space to escape the midday heat.

Lunch and Afternoon — St. Armands Circle and Lido Beach

From the aquarium, drive about 15–20 minutes across the bridge to St. Armands Circle, where parking is generally available in the central municipal lots and along the surrounding streets; read signs carefully for time limits. Have lunch at Columbia Restaurant, the long-established Spanish-Cuban favorite on the circle. Expect about $25–50 per person, and try the 1905 Salad or a Cuban sandwich if you want something lighter. Afterward, spend around 1½ hours browsing the independent shops, galleries, landscaped walkways, and public art around St. Armands Circle—it is compact and easy to explore on foot.

A short walk or five-minute drive brings you to Lido Beach, where the public beach access has restrooms, showers, and parking, although spaces become harder to find later in the afternoon. Set aside about 1½ hours to swim, walk the shoreline, or simply sit beneath the palms before dinner. Keep valuables out of the car, bring water, and check the Gulf conditions before entering; rip currents can occasionally develop even when the water looks calm.

Day 18 · Sat, Apr 11
Sarasota, FL

Sarasota

  1. The Ringling — North Sarasota; tour the art museum, circus museum, and grounds, morning (~3 hours).
  2. Yoder’s Restaurant — Pinecraft; classic Amish-Mennonite comfort food and pie, midday (~15–30 per person).
  3. Marie Selby Botanical Gardens — Downtown Sarasota; enjoy waterfront tropical gardens, afternoon (~2 hours).
  4. Sarasota Farmers Market — Downtown; browse local produce and prepared foods, late afternoon (~1 hour).
  5. Owen’s Fish Camp — Burns Court; atmospheric seafood dinner under banyan trees (~30–60 per person).

Morning — The Ringling

Make The Ringling your first stop, arriving close to its usual 10:00 AM opening so you have cooler weather and fewer school groups around the galleries. Set aside roughly three hours for the Museum of Art, Circus Museum, and the landscaped grounds; the Ca’ d’Zan mansion is worth adding if you have the energy, though it may require a separate timed admission. The complex is at 5401 Bay Shore Road, north of downtown, with free on-site parking; general admission is commonly around $25–35, with discounts and mansion access varying by ticket. Wear comfortable shoes—the grounds are more extensive than they look.

Lunch — Yoder’s Restaurant

Drive about 20 minutes south to Pinecraft, a quiet neighborhood with Amish and Mennonite roots, for lunch at Yoder’s Restaurant. Expect generous portions of fried chicken, meatloaf, sandwiches, and homestyle sides, with the famous pies saved for dessert; budget roughly $15–30 per person. It is a popular stop, so a short wait around lunchtime is normal. Afterward, take a relaxed drive toward downtown via U.S. 41, rather than trying to rush straight to the next stop.

Afternoon and late afternoon — Marie Selby Botanical Gardens and the Sarasota Farmers Market

Spend about two hours at Marie Selby Botanical Gardens, where the waterfront setting and tropical plant collections make a pleasant contrast to the morning’s formal museum. Allow around 20 minutes to drive from Yoder’s Restaurant; parking can be limited, so use the nearby public garages or street spaces if the garden lot is full. Admission is generally around $20–30, and hours often run from mid-morning into late afternoon, but check the official schedule for seasonal closing times. Later, walk or drive to the Sarasota Farmers Market around Main Street and Lemon Avenue. It is usually busiest on Saturday mornings, but if your date or schedule places you there later, browse the local produce, baked goods, and prepared-food stalls for about an hour; stall hours vary, so treat this as a flexible wander rather than a fixed appointment.

Evening — Owen’s Fish Camp

Finish in Burns Court at Owen’s Fish Camp, a relaxed seafood spot set beneath old banyan trees and strung with lights. It is roughly 10 minutes from the market by car, or an easy walk if you are already near downtown and don’t mind the heat. The menu changes with the catch, but expect Gulf seafood, oysters, fish sandwiches, and shareable sides; plan on $30–60 per person before drinks. Arrive early, around 5:00–5:30 PM, or be prepared to wait—reservations are limited and the atmosphere is deliberately casual.

Day 19 · Sun, Apr 12
St. Petersburg, FL

St. Petersburg

Getting there from Sarasota, FL
Rental car via I-75 and I-275, 1.25–1.5 hr, about $10–20 in fuel. Depart around 8:30 AM to reach St. Pete Beach before midday.
  1. Drive from Sarasota to St. Petersburg via I-75 and I-275 — Gulf Coast; allow ~1.25–1.5 hours, depart around 8:30 AM.
  2. St. Pete Beach — Barrier island; relaxed beach time after arrival, late morning (~2 hours).
  3. The Frog Pond — St. Pete Beach; popular brunch or lunch stop (~15–30 per person).
  4. Salvador Dalí Museum — Downtown St. Petersburg; see the major surrealist collection, afternoon (~2 hours).
  5. Central Avenue — Downtown; explore murals, independent shops, and galleries, late afternoon (~1.5 hours).
  6. Birchwood Canopy — Downtown; rooftop dinner and drinks (~35–70 per person).

Morning — St. Pete Beach

Leave Sarasota around 8:30 AM and drive via I-75 and I-275 to St. Pete Beach, allowing roughly 1¼–1½ hours. Aim to arrive before midday, when the barrier-island lots become harder to find and the Gulf heat intensifies. Settle in for about two hours on the sand near Pass-a-Grille Beach or the central public beach areas; bring water, sunscreen, and a little cash for parking, which commonly runs around $3–5 per hour or is metered depending on the lot. The water is usually pleasant in March, though afternoon breezes can pick up.

Lunch — The Frog Pond

For brunch or lunch, drive a few minutes inland to The Frog Pond, a long-running local favorite on Gulf Boulevard. Expect generous diner-style breakfasts, omelets, sandwiches, and seafood plates at roughly $15–30 per person. It can be busy late morning, so put your name down and use the wait to browse nearby shops rather than rushing. Afterward, drive across the causeway to downtown St. Petersburg—allow 20–30 minutes, with traffic—and use a paid garage or street parking near The Dalí Museum.

Afternoon and Evening — The Dalí Museum, Central Avenue, and Birchwood Canopy

Spend about two hours at The Dalí Museum, whose striking geodesic glass entrance is hard to miss on Dali Boulevard. Admission is generally around $30–35 for adults; reserve timed tickets online, particularly during spring-break periods, and check the museum’s current hours before setting out. From there, walk or drive north toward Central Avenue, spending the late afternoon moving between murals, independent stores, and small galleries. The most enjoyable stretch is around the downtown core and the Edge District, where you can wander without trying to see every block. Finish at Birchwood Canopy on Beach Drive Northeast for rooftop dinner and drinks, budgeting about $35–70 per person; reserve ahead for a sunset table, and expect the rooftop to be breezy even on a warm evening.

Day 20 · Mon, Apr 13
Clearwater, FL

Clearwater

Getting there from St. Petersburg, FL
Rental car via I-275 and the Sunshine Skyway area, 35–55 min, about $8–15 in fuel. A car is easiest for Clearwater Marine Aquarium and beach parking; book through the rental provider.
  1. Clearwater Marine Aquarium — Clearwater; visit a working marine-rescue center, morning (~2 hours).
  2. Frenchy’s Rockaway Grill — Clearwater Beach; casual Gulf-front seafood lunch (~20–40 per person).
  3. Clearwater Beach — Beach Walk; swim and relax on the broad sandy shore, afternoon (~2.5 hours).
  4. Pier 60 — Clearwater Beach; stroll the pier and browse sunset vendors, evening (~1 hour).
  5. Caretta on the Gulf — Clearwater Beach; refined sunset dinner (~50–90 per person).

Morning — Marine rescue on the waterfront

Start at Clearwater Marine Aquarium when it opens, ideally around 9:00 AM, before the larger family crowds arrive. Set aside about two hours for the rescue hospital, rehabilitation pools, and current animal residents; this is a working facility rather than a conventional aquarium, so exhibits and viewing areas can change with the animals’ needs. Admission is usually in the $35–45 range for adults, and advance tickets are sensible in April. Parking is available nearby, though it can fill quickly; from there, drive about 15–20 minutes over to Clearwater Beach.

Lunch — Gulf seafood at Frenchy’s Rockaway Grill

Have lunch at Frenchy’s Rockaway Grill, right on Clearwater Beach, and ask for an outdoor or beachfront table if the wait is reasonable. Expect roughly $20–40 per person before drinks and tip; grouper sandwiches, peel-and-eat shrimp, and the daily seafood specials are the reliable choices. After lunch, walk a few minutes to Beach Walk and spend the afternoon on Clearwater Beach. The broad sand is excellent for swimming and an unhurried beach break, but bring or rent an umbrella—midday sun is strong even in spring. Public parking and garages around the beach are convenient but often charge approximately $3–5 per hour, with rates varying by lot.

Evening — Sunset at the pier, then dinner

Around 5:30 PM, stroll down to Pier 60, where the end of the pier gives you a wide view west over the Gulf. The nightly sunset gathering typically begins about two hours before sunset, with local craft stalls, street performers, and casual browsing; the pier itself generally charges a small admission fee, often around $5. Stay through sunset, then walk or take a short rideshare along Clearwater Beach to Caretta on the Gulf at Sandpearl Resort. Reserve ahead for an ocean-facing table and allow $50–90 per person before drinks and gratuity. It is a polished finish to the day, with Gulf views and a more refined menu than lunch—aim for a reservation around 7:30 PM, adjusting it to that evening’s sunset time.

Day 21 · Tue, Apr 14
Tampa, FL

Tampa

Getting there from Clearwater, FL
Rental car via Courtney Campbell Causeway/FL-60, 45–60 min, about $7–15 in fuel. Depart around 8:30 AM; allow extra time for rush-hour traffic.
  1. Drive from Clearwater to Tampa via Courtney Campbell Causeway — Clearwater–Tampa; allow ~45–60 minutes, depart around 8:30 AM.
  2. Tampa Riverwalk — Downtown; follow the riverfront past parks and museums, morning (~1.5 hours).
  3. Tampa Museum of Art — Downtown; see modern and classical works, late morning (~1.5 hours).
  4. Ulele — Tampa Heights; inventive Florida-inspired lunch on the river (~30–60 per person).
  5. Armature Works — Tampa Heights; browse the food hall and waterfront promenade, afternoon (~1.5 hours).
  6. Sparkman Wharf — Channel District; casual dinner and outdoor games, evening (~25–45 per person).

Morning — Riverfront Tampa

Leave Clearwater around 8:30 AM for Tampa via FL-60 and the Courtney Campbell Causeway, allowing 45–60 minutes and extra time for weekday traffic. In Tampa, park in a downtown garage near Curtis Hixon Waterfront Park; street parking is limited, and the city’s garages are generally the least stressful option. Start with a 1½-hour walk along the Tampa Riverwalk, heading south beside the Hillsborough River and passing Water Works Park, Kiley Gardens, and the waterfront museums. It is cooler and quieter in the morning, and the route is flat and easy.

Continue to the Tampa Museum of Art, a short walk along the Riverwalk. Allow about 1½ hours for its modern, classical, and contemporary collections; check the official schedule for current opening hours and admission, typically around $25 for adults. The museum’s building and river views are worth a few minutes even if you are not a serious gallery-goer. From here, it is roughly a 10-minute drive—or a pleasant 20-minute walk north—to Tampa Heights.

Lunch and Afternoon — Tampa Heights

Have lunch at Ulele, housed in a former waterworks building beside the river. Its menu leans into Florida ingredients—think local seafood, oysters, and inventive takes on regional comfort food—and lunch usually works out at about $30–60 per person before drinks and tip. Reservations are useful, particularly on a weekend, though the spacious bar is often the easiest place to find a seat. After lunch, walk across to Armature Works, the restored Heights Public Market. Browse the food stalls, then take your time along the riverfront promenade toward Water Works Park; the whole stop fits comfortably into 1½ hours without needing to order another full meal.

Evening — Channel District

For dinner, drive or rideshare about 10–15 minutes to Sparkman Wharf in the Channel District. This open-air waterfront complex is best approached casually: choose from the rotating food vendors, grab a drink, and settle near the lawn or outdoor games. Expect roughly $25–45 per person, depending on drinks and how much you order. It is a good place to end the day because you can linger rather than committing to a formal restaurant; check vendor hours before heading over, as individual kitchens sometimes close earlier than the main space.

Day 22 · Wed, Apr 15
Tampa, FL

Tampa neighborhoods

  1. Ybor City — Historic district; explore cigar-era architecture and cultural landmarks, morning (~2 hours).
  2. Columbia Restaurant — Ybor City; landmark Spanish-Cuban lunch (~25–50 per person).
  3. Tampa Bay History Center — Channel District; understand the region’s Indigenous, maritime, and immigrant history, afternoon (~2 hours).
  4. Berns Steak House — Hyde Park; iconic dinner and extensive dessert-room experience (~100–200 per person).
  5. Hyde Park Village — Hyde Park; evening stroll through shops and restaurants, late evening (~1 hour).

Morning — Ybor City

Begin around 9:00 AM in Ybor City, Tampa’s historic cigar district, and allow about two hours to wander without rushing. Start near 7th Avenue and Centro Ybor, then follow the brick sidewalks past the old cigar factories, iron balconies, and colorful storefronts. Look for the district’s historic street signs and the small Ybor City Museum State Park courtyard; the museum itself is usually open from 9:00 AM to 5:00 PM and costs only a few dollars, though the surrounding streets are the main attraction. The area is quieter in the morning than later in the day, and the free TECO streetcar is useful if you want to avoid walking the full distance—ride it toward the Channel District afterward, or take a short rideshare to your next stop.

Lunch — Columbia Restaurant

Have lunch at Columbia Restaurant on 7th Avenue, Tampa’s grand Spanish-Cuban institution. Reserve ahead if possible, particularly for a weekend, and plan on roughly $25–50 per person. The 1905 salad, Cuban sandwich, and seafood dishes are reliable choices, while the tiled dining rooms and old photographs provide much of the atmosphere. Take your time here; it is a proper sit-down lunch rather than a quick stop, and a late lunch around 12:00–12:30 PM helps you avoid the busiest midday period.

Afternoon — Tampa Bay History Center

After lunch, head to the Tampa Bay History Center in the Channel District, about 10 minutes by rideshare or roughly 15–20 minutes on the TECO streetcar, depending on where you board. Spend around two hours with the exhibits on the area’s Indigenous communities, Spanish exploration, maritime trade, cigar-making, and immigrant neighborhoods. It is generally open from 10:00 AM to 5:00 PM, with admission commonly around $15–20 for adults; check the official schedule for current pricing and special exhibitions. The nearby Cotanchobee Fort Brooke Park is a pleasant place to pause by the water before dinner.

Evening — Bern’s Steak House and Hyde Park Village

Make a reservation at Bern’s Steak House in Hyde Park well in advance; this is not a walk-in dinner, and the full experience can last several hours. Expect approximately $100–200 per person before drinks and gratuity. Order the steakhouse dinner at an unhurried pace, then continue to the famous Harry Waugh Dessert Room if available—reservations or a post-dinner wait may apply. Afterwards, take a short rideshare to Hyde Park Village for an easy late-evening stroll around the open-air shops, landscaped courtyards, and cafés. Most retail stores close around 7:00–8:00 PM, but the dining areas stay active later; use a rideshare rather than moving the car, as parking around Bern’s Steak House and Hyde Park Village can be inconvenient at dinner time.

Day 23 · Thu, Apr 16
Orlando, FL

Orlando arrival

Getting there from Tampa, FL
Rental car via I-4, 1.5–2 hr, about $15–25 in fuel. Depart around 8:30 AM; reserve hotel or attraction parking.
  1. Drive from Tampa to Orlando via I-4 — Central Florida; allow ~1.5–2 hours, depart around 8:30 AM; use hotel or attraction parking.
  2. Disney Springs — Lake Buena Vista; lively arrival-day shopping, entertainment, and waterfront walking, late morning (~2 hours).
  3. The Polite Pig — Disney Springs; convenient barbecue lunch (~20–35 per person).
  4. Orlando International Premium Outlets — International Drive; browse major outlet stores, afternoon (~2 hours).
  5. The Wheel at ICON Park — International Drive; panoramic evening views, sunset (~1 hour).
  6. The Hampton Social — ICON Park area; relaxed dinner and cocktails (~30–60 per person).

Morning — Tampa to Disney Springs

Leave Tampa around 8:30 AM via I-4 for Orlando, allowing roughly 1½–2 hours depending on traffic. Once you arrive in the Lake Buena Vista area, follow signs for Disney Springs and use the large complimentary parking garages; the Orange Garage is particularly convenient for the Town Center and Marketplace. The shopping-and-dining district generally opens from late morning, so this timing works well after the drive without forcing an early start. Spend about two hours wandering the waterfront, browsing the shops, and taking in the resort atmosphere—there is no admission charge, though individual attractions and entertainment cost extra.

Lunch — The Polite Pig

Have lunch at The Polite Pig, a casual barbecue restaurant in Disney Springs’ Town Center, ideally before the main midday rush. Expect around $20–35 per person for smoked meats, vegetables, sandwiches, and drinks; counter service makes it easy to keep the day moving. Afterward, allow about 25–35 minutes to drive to Orlando International Premium Outlets on International Drive. The route can be slow around I-4 and the theme-park exits, and outlet parking is free but busiest near the central entrances.

Afternoon — International Drive shopping

Set aside roughly two hours at Orlando International Premium Outlets, where the long open-air complex is good for a relaxed browse through major fashion, sportswear, and luggage brands. Wear comfortable shoes and keep purchases in the car rather than carrying them through the rest of the afternoon. From the outlets, The Wheel at ICON Park is about a 10-minute drive along International Drive; arrive with enough time to park and reach the entrance before your preferred sunset window. The enclosed observation wheel takes around 20 minutes to complete a rotation, with broad views across the Orlando skyline and, on a clear day, the distant theme-park area. Tickets commonly cost roughly $30–40 for adults, but check the current schedule and book ahead for sunset.

Evening — The Hampton Social

Finish at The Hampton Social, beside ICON Park, for dinner and cocktails. It is a convenient walk from the wheel, so there is no need to move the car; allow around $30–60 per person depending on drinks and what you order. The dining room has a lively coastal feel, while the outdoor seating is pleasant in March. After dinner, return to your hotel by rideshare or car, allowing extra time on International Drive if you are staying outside the immediate tourist district.

Day 24 · Fri, Apr 17
Orlando, FL

Orlando

  1. Universal Islands of Adventure — Universal Orlando; spend the day on major rides and themed lands, morning–afternoon (~6 hours).
  2. The Leaky Cauldron — Universal’s Wizarding World; themed lunch inside Diagon Alley’s neighboring land (~20–40 per person).
  3. Universal CityWalk — Universal Orlando; browse entertainment venues after the park, evening (~1.5 hours).
  4. Vivo Italian Kitchen — CityWalk; sit-down Italian dinner (~25–50 per person).

Morning — Universal Islands of Adventure

Arrive at Universal Islands of Adventure around 8:00–8:30 AM, before the official opening rush; check the park app for that day’s opening time and early-entry access. Use the resort parking garages, then take the moving walkways toward the park entrance—allow 20–30 minutes from parking to the gates. Spend the morning on the headline rides and themed lands, prioritizing the attractions with the longest waits while energy is high. The park is large but straightforward to navigate, and six hours is enough for a strong first pass without trying to do absolutely everything. Wear comfortable shoes, bring sunscreen and a refillable bottle, and use the app for live wait times and virtual-line information where offered.

Lunch — The Leaky Cauldron

Around midday, make your way to The Leaky Cauldron in the Wizarding World of Harry Potter—Diagon Alley for a themed lunch. Allow 20–40 minutes depending on the queue; the menu is British-leaning, with hearty plates, fish and chips, and vegetarian options, generally around $20–40 per person. If you are carrying bags or souvenirs, consider using the park’s lockers before riding attractions with loose belongings. After lunch, return to your preferred lands for another couple of hours, leaving some time to browse the detailed shops and atmospheric streets rather than racing between rides.

Evening — Universal CityWalk and Vivo Italian Kitchen

Exit through the parking-garage route into Universal CityWalk, where you can spend roughly 1½ hours browsing the shops, entertainment venues, and waterfront promenade. It is liveliest after the parks close, so expect crowds and a little waiting at popular venues; CityWalk admission itself is generally free, though individual entertainment costs extra. Have dinner at Vivo Italian Kitchen, a convenient sit-down choice with handmade pasta, pizza, and substantial mains, usually about $25–50 per person before drinks and gratuity. Reservations are useful at peak dinner hours, but arriving slightly before 6:00 PM often gives you a better chance of a shorter wait.

Day 25 · Sat, Apr 18
Winter Park, FL

Winter Park

Getting there from Orlando, FL
SunRail from an appropriate Orlando station to Winter Park, about 25–40 min, approximately $2–5. Check weekday/weekend schedules on SunRail.com; rideshare is better if traveling early on a weekend.
  1. Drive from Orlando to Winter Park — Orlando–Winter Park; allow ~20–30 minutes, depart around 8:30 AM.
  2. Winter Park Scenic Boat Tour — Winter Park; cruise through interconnected lakes and canals, morning (~1 hour).
  3. Park Avenue — Winter Park; browse galleries, boutiques, and cafés, late morning (~1.5 hours).
  4. The Ravenous Pig — Winter Park; acclaimed modern Florida lunch (~30–60 per person).
  5. Charles Hosmer Morse Museum of American Art — Winter Park; see an exceptional Tiffany collection, afternoon (~2 hours).
  6. Mead Botanical Garden — Winter Park; finish with a quiet nature walk, late afternoon (~1 hour).

Morning — Lakes and canals

Leave Orlando around 8:30 AM and allow 20–30 minutes to reach Winter Park. A rideshare is the easiest option for an early start; SunRail is inexpensive—roughly $2–5—but check the weekend timetable, as service is less convenient on Sundays. Head first to Winter Park Scenic Boat Tour, departing from the dock near Park Avenue. The roughly one-hour cruise through the chain of lakes and narrow canals is a lovely introduction to Winter Park’s leafy, old-Florida character. Arrive 15–20 minutes early; boats can fill, and the schedule may change with weather.

Late Morning and Lunch — Park Avenue

After the cruise, walk along Park Avenue, the town’s polished but pleasantly relaxed main street. Browse the independent galleries, boutiques, and shaded side streets for about 1½ hours, taking time to wander east toward Central Park rather than staying only on the busiest retail stretch. For lunch, settle at The Ravenous Pig, a well-regarded modern Florida restaurant with house-made charcuterie, seasonal plates, and a strong beer list. Expect roughly $30–60 per person before drinks and tip; reservations are useful, particularly on a Sunday, and a rideshare or short walk from central Park Avenue is usually simpler than moving the car.

Afternoon — Tiffany glass and a garden walk

Spend the afternoon at the Charles Hosmer Morse Museum of American Art, a short walk from Park Avenue. Allow about two hours for its outstanding collection of Louis Comfort Tiffany glass, jewelry, furnishings, and chapel interiors; admission is generally around $8–15, with reduced or free-entry periods sometimes offered, so check the museum’s current schedule. Finish at Mead Botanical Garden, about a 10-minute drive north. Its shaded paths, wetlands, boardwalks, and native plantings make for an unhurried final hour, and entry is typically free. The garden closes before evening, so check the same-day hours and leave enough time to enjoy it rather than rushing through.

Day 26 · Sun, Apr 19
Cocoa Beach, FL

Space Coast

Getting there from Winter Park, FL
Rental car via FL-528, about 1 hr, approximately $10–18 in fuel. Depart around 7:30 AM for Kennedy Space Center. Book via Rentalcars.com, Discover Cars, or directly with the provider.
  1. Drive from Orlando to Cocoa Beach via FL-528 — Orlando–Space Coast; allow ~1 hour, depart around 7:30 AM.
  2. Kennedy Space Center Visitor Complex — Merritt Island; explore NASA history and the shuttle program, morning–afternoon (~5–6 hours).
  3. The Space Bar — Cocoa Beach; casual seafood lunch with ocean views (~20–40 per person).
  4. Cocoa Beach Pier — Cocoa Beach; walk the historic pier and watch surfers, late afternoon (~1 hour).
  5. Coconuts on the Beach — Cocoa Beach; beachside dinner and sunset atmosphere (~25–50 per person).

Morning — Kennedy Space Center Visitor Complex

Leave Winter Park around 7:30 AM in the rental car, taking FL-408 east toward FL-528 and then following the signs for the Kennedy Space Center Visitor Complex on Merritt Island. The drive is usually about an hour, but allow extra time for tolls, merging traffic, and the large visitor parking area. Aim to arrive shortly before opening; admission is commonly around $75–$80 for adults, with add-ons and special tours costing more. Plan on five to six hours here: prioritize the Space Shuttle Atlantis exhibit, the Apollo/Saturn V Center bus tour, and the main rocket displays rather than trying to see every film and gallery.

Lunch — The Space Bar

After leaving the space center, drive roughly 25–35 minutes south to The Space Bar in Cocoa Beach. It is a good first taste of the beach town: casual, unfussy seafood, outdoor seating, and broad ocean views. Expect about $20–$40 per person before drinks; service can slow during the midday rush, so this is a place to settle in rather than hurry through. If you still have room, look for a local fish special or shrimp dish rather than defaulting to the standard beach fare.

Late Afternoon — Cocoa Beach Pier

From The Space Bar, it is a short drive or a longer beachside walk to Cocoa Beach Pier; driving is more practical with bags, though parking can fill on a sunny afternoon. Set aside about an hour to stroll the historic pier, watch surfers below, and browse the small shops and concession stands. The pier charges for parking in many areas, and beach access is easiest if you bring sandals, sunscreen, and a little cash. Late afternoon is the nicest time here, when the light softens and the heat begins to ease.

Evening — Coconuts on the Beach

Finish at Coconuts on the Beach, a short walk from the pier and one of the more convenient spots for a relaxed beach-town dinner. Expect roughly $25–$50 per person, depending on seafood and drinks; outdoor tables are especially pleasant as the sun drops, though seating is first-come or may involve a wait. After dinner, walk a few minutes onto Cocoa Beach for the evening atmosphere, but keep the return drive in mind if you are staying inland: the route back toward Winter Park is darker and quieter after FL-528, so avoid rushing and check the rental car’s fuel level before leaving.

Day 27 · Mon, Apr 20
St. Augustine, FL

St. Augustine

Getting there from Cocoa Beach, FL
Rental car via US-1 and I-95, 2.5–3 hr, about $20–35 in fuel. Depart around 7:30 AM to preserve the full sightseeing day.
  1. Drive from Cocoa Beach to St. Augustine via US-1 and I-95 — Space Coast–St. Augustine; allow ~2.5–3 hours, depart around 7:30 AM.
  2. Castillo de San Marcos National Monument — Historic district; tour the oldest masonry fort in the continental United States, late morning (~2 hours).
  3. The Floridian — Historic district; seasonal Southern lunch, midday (~20–40 per person).
  4. St. George Street — Historic district; browse pedestrian shops and historic buildings, afternoon (~1.5 hours).
  5. Lightner Museum — Historic district; explore Gilded Age collections in a former hotel, late afternoon (~1.5 hours).
  6. St. Augustine Lighthouse & Maritime Museum — Anastasia Island; climb for coastal views before dinner (~1.5 hours).

Morning

Leave Cocoa Beach around 7:30 AM for St. Augustine, allowing 2½–3 hours via US-1 and I-95, with a little extra time for weekday traffic near Jacksonville. Once in town, head straight to Castillo de San Marcos National Monument. The fort is best before the historic district becomes crowded; allow about two hours to explore the rooms, ramparts, and harbor views. Admission is typically around $15 per adult, and parking around the historic district is limited, so the St. Augustine Historic Downtown Parking Facility on West Castillo Drive is the easiest base.

Lunch and Historic District

Walk from the fort through the old lanes to The Floridian on Spanish Street for a relaxed Southern lunch, usually $20–40 per person. Seasonal dishes, local produce, and a shaded courtyard make it a better-paced stop than a quick tourist meal; reservations are useful if available. After lunch, spend roughly 1½ hours wandering St. George Street, dipping into the side lanes and small courtyards rather than staying only on the busiest pedestrian stretch. Keep some flexibility here—Aviles Street and the nearby historic residential blocks are especially pleasant for a quieter look at the city.

Late Afternoon and Evening

Continue to Lightner Museum, a short walk away on King Street, and allow about 1½ hours for its eclectic Gilded Age collections inside the former Alcazar Hotel. The museum generally closes in the late afternoon, so check the day’s hours and arrive with enough time before last entry; admission is commonly around $15–20. From downtown, drive or use a rideshare across the Bridge of Lions to St. Augustine Lighthouse & Maritime Museum on Anastasia Island—roughly 10 minutes by car. Set aside 1½ hours for the lighthouse and maritime exhibits, and climb only if you are comfortable with the 219 steps; late-day light gives the best coastal views. Check the museum’s closing time before setting out, since it can vary seasonally.

Day 28 · Tue, Apr 21
Jacksonville, FL

Jacksonville departure

Getting there from St. Augustine, FL
Rental car via I-95, about 1 hr, approximately $8–15 in fuel. Depart around 8:30 AM; allow 25–35 minutes from downtown to Jacksonville International Airport and arrive at least 2 hours before the flight.
  1. Drive from St. Augustine to Jacksonville via I-95 — St. Augustine–Jacksonville; allow ~1 hour, depart around 8:30 AM.
  2. Cummer Museum of Art & Gardens — Riverside; finish with major art collections and riverfront gardens, morning (~2 hours).
  3. Five Points — Riverside; browse independent shops and cafés, midday (~1 hour).
  4. Hawkers Asian Street Fare — Five Points; casual lunch with shareable plates (~20–40 per person).
  5. Jacksonville-Baldwin Rail Trail — West Jacksonville; final outdoor walk or bike ride, afternoon (~1.5 hours).
  6. Jacksonville International Airport — North Jacksonville; allow ~25–35 minutes from downtown, arriving at least 2 hours before departure.

Morning — Cummer Museum of Art & Gardens

Leave St. Augustine around 8:30 AM for Jacksonville via I-95, allowing about an hour before city traffic and time to return the rental car later. Head first to the Cummer Museum of Art & Gardens in Riverside; allow roughly two hours for the major collections and the beautifully laid-out gardens beside the St. Johns River. The museum typically opens at 11:00 AM on some weekdays, so check the official schedule before setting out and adjust your departure if necessary. Garden access and admission policies can vary; expect around $15–20 for an adult ticket, with parking available nearby or in the museum’s lot when open.

Midday — Five Points and lunch at Hawkers Asian Street Fare

From the museum, it is a short walk or quick rideshare to Five Points, the lively heart of Riverside. Spend about an hour browsing independent boutiques, record shops, cafés, and the side streets around Park Street rather than rushing from storefront to storefront. Settle in at Hawkers Asian Street Fare for shareable plates—roti canai, dumplings, noodles, and other Southeast Asian-inspired dishes—with lunch generally costing about $20–40 per person before drinks and tip. It can be busy around noon, so joining the waitlist in advance is worthwhile.

Afternoon — Jacksonville-Baldwin Rail Trail and departure

After lunch, drive west to the Jacksonville-Baldwin Rail Trail for a final hour and a half outdoors. The trail is flat and relaxed, with shaded stretches through pine woods and wetlands; walking is free, while bike rentals may require arranging equipment ahead of time because there is not always a rental shop directly at the trailhead. Keep this stop flexible if your flight is early: from downtown Jacksonville, allow about 25–35 minutes to reach Jacksonville International Airport, plus time to refuel and return the rental car. Aim to arrive at least two hours before departure, and leave the trail with a generous buffer for I-95 and airport traffic.

0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version