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5-Day South Florida & Gulf Coast Road Trip: Miami → Key West → Naples → Sanibel/Fort Myers → Sarasota → Orlando

Viewed by 652 travelers

Day 1: Miami highlights

Miami, USA on August 13, 2025

8:00am

Breakfast — The Front Porch Café (South Beach)

Classic South Beach breakfast spot right by Ocean Drive; great for outdoor people-watching and reliable American breakfasts. Open early (≈8:00am) and good to fuel up before walking the Art Deco District.
USD15, 1h0m

9:00am

Art Deco Historic District walking tour (self-guided or guided)

See Miami Beach's pastel, 1920s–1940s architecture along Ocean Drive and Collins Avenue; guided tours typically run 60–90 minutes and explain the history and design. Tours and self-guides operate in the morning; guided tours often start ~9:00am.
USD0, 1h30m

11:00am

Lincoln Road / Shopping stroll

Pedestrian promenade with shops, galleries and cafés — an easy late-morning walk after the Art Deco tour. Most shops open by 11:00am on weekdays.
USD0, 1h0m

12:30pm

Lunch — Joe’s Take Away or nearby seafood spot

Classic Miami seafood (if Joe’s Stone Crab full service is busy, use the take-away counter for a quicker meal); good to try local seafood or a Cuban sandwich for a Miami lunch. Restaurants typically open 11:30am–12:00pm for lunch.
USD30, 1h0m

2:30pm

Wynwood Walls & street art (Wynwood)

Outdoor mural park showcasing large-scale street art and rotating exhibits; open roughly 10:00am–7:00pm (hours vary seasonally). Great for photos and a very different Miami vibe.
USD12, 1h30m

5:00pm

Little Havana — Calle Ocho stroll

Walk the cultural heart of Miami’s Cuban community: try a cortadito, watch domino players at Máximo Gómez Park, and browse Cuban bakeries and cigar shops. Most shops and cafés are open into the evening.
USD10, 1h30m

7:00pm

Dinner — Versailles Restaurant (Little Havana) or similar Cuban spot

Iconic Cuban restaurant known for classics like ropa vieja, tostones and strong Cuban coffee; casual, lively dinner option open late (often until 10–11pm).
USD25, 1h30m

Day 2: Florida Keys day

Key West, USA on August 14, 2025

7:00am

Drive — Miami to Key West (US-1 Overseas Highway)

Scenic drive over the Florida Keys; plan ~3.5–4 hours without long stops but build in time for photos at the bridges. Gas and rest stops available along the route; leave early to maximize Key West time.
USD30, 4h0m

11:00am

Ernest Hemingway Home & Museum

Historic house museum where Hemingway lived (open ~9:00am–5:00pm); see the home, gardens and famous polydactyl cats. Tickets typically sold at the gate with timed entry recommended.
USD17, 1h0m

12:30pm

Lunch — Blue Heaven

Beloved Key West spot known for island-style breakfasts and seafood; popular for its relaxed outdoor courtyard and local flavor. Open for lunch/late breakfast (often from ~8:00am).
USD20, 1h0m

2:00pm

Southernmost Point & Duval Street

Photo stop at the Southernmost Point buoy and a stroll along Duval Street’s shops, bars and galleries — classic Key West walking exploring, open all day.
USD0, 1h30m

3:30pm

Key West Butterfly & Nature Conservatory

Indoor/outdoor conservatory with hundreds of butterflies and tropical birds; open ~9:00am–5:00pm, a calm mid-afternoon activity and good for families.
USD15, 1h0m

6:30pm

Mallory Square sunset (street performers)

Famous Key West sunset celebration with performers and vendors; arrive 30–60 minutes before sunset to get a good spot — sunset times vary but arrive early evening in August.
USD0, 1h0m

7:30pm

Dinner — El Meson de Pepe or El Siboney

Enjoy Cuban/Latin dishes or hearty island fare close to Mallory Square; both open into the evening and offer relaxed, authentic island dining.
USD25, 1h30m

9:30pm

Overnight in Key West

Stay in Old Town to keep walking access to Duval Street and the waterfront — book ahead, especially in high season.
USD0, —

Day 3: Coastal Naples

Naples, USA on August 15, 2025

8:00am

Drive — Key West to Naples (return across mainland)

Long drive (~4.5–5 hours) back across the lower Keys and Everglades to the Gulf Coast; leave early and plan rest stops. Consider a coffee stop in Homestead or Everglades City.
USD40, 5h0m

1:00pm

Arrival & quick stroll — Naples downtown/3rd Street South

Upscale shopping and shaded sidewalks with galleries and cafés — a pleasant first stop to stretch after the drive, most shops open by midday.
USD0, 0h45m

1:30pm

Lunch — The Dock at Crayton Cove

Waterfront restaurant serving seafood and Floridian favorites; good views of the marina and convenient for exploring Naples afterward. Typical lunch hours 11:00am–3:00pm.
USD30, 1h0m

3:00pm

Naples Pier & beach time

Relax on the white-sand beach and walk the historic Naples Pier (open daylight hours); great for swimming, shelling and sunset photographing. Beach access is generally open dawn–dusk.
USD0, 2h0m

5:30pm

Naples Botanical Garden (optional)

If you prefer gardens to the beach, the botanical garden showcases tropical plants and walking paths; open typically ~8:30am–5:00pm — check seasonal hours.
USD20, 1h0m

7:00pm

Dinner — The Turtle Club or waterfront restaurant

Enjoy Gulf-coast seafood and a sunset atmosphere; many Naples restaurants offer outdoor seating and seafood specialties. Most dinner services begin ~5:00pm–6:00pm.
USD40, 1h30m

Day 4: Everglades & Islands

Sanibel / Fort Myers, USA on August 16, 2025

7:30am

Drive — Naples to Shark Valley (Everglades) / or Everglades City

Head east/northeast for an Everglades nature experience; Shark Valley Visitor Center (Everglades NP) is a well-run option for wildlife viewing and tram/bicycle tours. Drive ~1.5–2 hours depending on which entrance you use.
USD20, 1h30m

9:00am

Shark Valley Tram Tour or self-bike loop (Everglades National Park)

Two-hour tram tour (or self-guided bike along the 15-mile loop) to see alligators and wading birds; Shark Valley hours typically ~8:00am–5:00pm and trams run frequently — reserve tram tickets if possible.
USD30, 2h0m

12:00pm

Drive — Everglades to Sanibel Island / Fort Myers

Drive west to the Gulf islands; allow ~1.5–2 hours to reach Sanibel/Periwinkle area depending on traffic.
USD20, 2h0m

2:00pm

Lunch — Gramma Dot’s Seaside Saloon (Sanibel)

Casual island eatery popular for seafood and relaxed lunches near the water; ideal for sampling local flavors before an afternoon of shelling.
USD20, 1h0m

3:30pm

Beach & shelling — Bowman’s Beach / Sanibel Lighthouse

Sanibel is famous for shelling; visit Bowman’s Beach or the area around the lighthouse for low-tide shell hunting and quiet beaches (parks open dawn–dusk).
USD0, 2h0m

6:30pm

Drive to Fort Myers (optional Captiva detour)

If you want sunset views and a lively dining scene, continue to Fort Myers or Captiva; Captiva’s Bubble Room is an iconic, eclectic dining option (book ahead).
USD10, 0h30m

7:30pm

Dinner — The Bubble Room (Captiva) or local Fort Myers seafood

Choose an island-styled dinner spot for fresh seafood or creative, family-friendly dining; many places stay open late into evening hours.
USD35, 1h30m

Day 5: Culture to theme parks

Sarasota → Orlando, USA on August 17, 2025

8:00am

Drive — Fort Myers/Sanibel to Sarasota

Head north along I-75 for Sarasota to visit museums and beaches; drive time roughly 1.5–2 hours depending on traffic.
USD15, 2h0m

10:30am

The Ringling Museum (Sarasota)

Comprehensive complex with art museum, circus museum, and Ca' d'Zan mansion; the museum typically opens at 10:00am — allocate 2–3 hours to see highlights.
USD25, 2h30m

1:30pm

Lunch — Selva Grill or downtown Sarasota

Fresh, Latin-influenced coastal cuisine in downtown Sarasota; a convenient lunch before the drive to Orlando.
USD25, 1h0m

3:00pm

Drive — Sarasota to Orlando

Drive inland on I-4 toward Orlando; expect ~2–2.5 hours depending on traffic. Plan arrival mid-late afternoon to check into your Orlando hotel or visit a quick attraction.
USD20, 2h30m

5:30pm

ICON Park / The Wheel or Disney Springs (evening options)

ICON Park on International Drive offers a ferris wheel, restaurants and shops (open into the evening). Alternatively, head to Disney Springs for free evening entertainment and shopping (open late).
USD28, 1h30m

7:30pm

Dinner — The BOATHOUSE (Disney Springs) or local Orlando restaurant

Waterfront dining with seafood and steaks; a relaxing final-night dinner with plenty of options at Disney Springs or nearby International Drive restaurants (most open late).
USD40, 1h30m

9:30pm

Evening — Optional mini attraction or relax

Finish with a nighttime stroll, spa, or early rest depending on your departure plans the next day. Orlando offers late-night entertainment options if you’re not flying out early.
USD0, —
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