Start with a roughly two-hour wander through South Beach and the Art Deco Historic District. Follow Ocean Drive and Collins Avenue to admire the pastel façades and geometric details, then fit in a short beach break if the weather cooperates. It’s hot and humid in September, so bring water, sunscreen, and swimwear; allow extra time for a dip. Street parking can be scarce and metered, so a paid garage is usually less stressful—check posted rates and restrictions before leaving the car.
Head to Versailles Restaurant in Little Havana for Cuban classics; budget about $15–30 per person, and expect a lively, sometimes busy dining room. After lunch, explore Calle Ocho at an easy pace: browse the shops and murals, and pause for Cuban coffee or something sweet. The restaurant sits right on Calle Ocho, so you can continue on foot rather than moving the car. From South Beach, allow roughly 25–45 minutes by car to Little Havana, depending on Saturday traffic; rideshare is another convenient option.
Finish at Wynwood Walls, the outdoor gallery of large-scale murals in Wynwood. Allow about 1½ hours, and check current hours, admission, and ticket requirements before you go—access and pricing can change. From Little Havana, the drive is usually around 15–25 minutes; paid lots are common nearby, but check the signs and rates. September afternoons can bring sudden rain, so have a light layer handy and leave a little flexibility in your timing.
Leave Miami in the morning for the roughly 2–2.5-hour drive down the Overseas Highway. Traffic, a fuel stop, and hotel bag drop can add time, so treat the beach as the day’s main event rather than trying to pack in several stops. You’ll have the car for getting around Islamorada; allow a little extra time for parking and the short drives along US-1.
Spend a couple of hours at Anne’s Beach, a laid-back spot with shallow water and a boardwalk. Bring water, sun protection, and beach shoes, and check local conditions before swimming. Facilities and parking can be limited, so don’t count on a long stretch of shade or an easy space right at the beach.
Head to Robbie’s of Islamorada for lunch and a relaxed waterfront break. Budget roughly $20–40 per person for a meal, and expect waits at busy times. Any tarpon-feeding activity is separate from dining; check current prices and availability if you’re interested.
If you arrive with enough time, finish at the History of Diving Museum on Upper Matecumbe Key, allowing about 1.5 hours. Its Sunday schedule may differ or change, so verify opening hours and admission before setting out; if timing is tight, keep the beach time and skip the museum rather than rushing through both.
Leave Islamorada in the morning and allow about an hour to reach Marathon, plus a little time to drop your bags or check in. Aim to arrive in time for your reserved late-morning tour at The Turtle Hospital; tours are guided and advance booking is important, so confirm the time and arrive early. Plan on about 1½ hours there. The visit is indoors and air-conditioned—a welcome break if the Keys are already heating up.
From the hospital, drive toward the Old Seven Mile Bridge area for your visit to Pigeon Key. Give yourself around two hours for the island and its water views, but check current access and tour arrangements before you go: reaching the island depends on the operating visitor transport, and access can change. Wear comfortable shoes, bring water and sun protection, and leave a little flexibility in case the transfer schedule affects your visit.
Head to Island Fish Company for a relaxed waterfront dinner as the day winds down. Budget about $25–45 per person and roughly 1½ hours; sunset views make it a popular stop, so check current hours and consider calling ahead, especially for an outdoor table. You’ll want a car or taxi for the return to your Marathon lodging, as the restaurant isn’t an easy walk from most places to stay.
Leave Marathon in the morning and allow about 45 minutes to reach Bahia Honda State Park; with the planned two-hour stop, parking and the onward drive, expect to reach Key West around early afternoon before check-in. At the park, stretch your legs on the beach and take in the views of the old bridge. The park is generally open from 8 a.m. to sunset, but beach conditions and access can change, so check the park’s current alerts before setting out. Budget roughly $8 per vehicle for admission, subject to current fees, and allow extra time if the entrance backs up.
After the roughly 45-minute drive from the park, check in and leave the car at your lodging or a paid lot; parking around Old Town can be tight, and walking or a rideshare is often easier than moving the car again. Later, make your way to the Southernmost Point Buoy for a quick photo. It’s a popular stop, so a 30-minute visit is sensible, but the queue can stretch—build in a little flexibility rather than rushing straight to dinner.
Walk or take a short rideshare to Santiago’s Bodega in Bahama Village for a relaxed tapas dinner. Plan on about 1½ hours and roughly $30–50 per person before drinks and tip; booking ahead is wise, especially for dinner, and check current hours as they can vary. This is a good evening to settle in and share a few dishes rather than trying to fit in another stop.
Start at the Ernest Hemingway Home and Museum in Old Town. The house and gardens are usually open daily from 9 a.m. to 5 p.m.; allow about 1½ hours for the guided tour and time to meet the famous six-toed cats. Admission is roughly $19 per adult, but check current prices and tour details before you go. September heat builds quickly, so arrive near opening and bring water.
Walk about 10 minutes to Blue Heaven for a leisurely brunch in its leafy garden. It’s a popular stop, so expect a possible wait; brunch is generally served until mid-afternoon, but check the day’s hours. Budget about $20–40 per person, depending on what you order. Afterward, stroll back toward the lighthouse area rather than rushing—the shady residential streets are part of the charm.
Visit the Key West Lighthouse and Keeper’s Quarters Museum, across from the Hemingway home. Give yourself about an hour to climb the tower and explore the exhibits; check current hours and admission before setting out, as the climb involves a steep staircase. Later, make your way to Mallory Square for the sunset gathering and street performers. It’s an easy walk from Old Town; arrive 30–45 minutes before sunset to find a spot along the waterfront, and bring a little cash if you’d like to tip performers.
Head to Fort Zachary Taylor Historic State Park for a relaxed final beach walk and a look around the Civil War-era fort. Plan on about 1½–2 hours; the park and fort generally open in the morning, but check current hours and access before setting out. Admission is typically around $6 per vehicle for up to two people, with a small additional charge for extra passengers. From Old Town, a taxi or rideshare is usually the easiest option; biking takes roughly 10–15 minutes, though you’ll need to manage your bags separately.
Continue to Sandy’s Café near the airport for coffee and a Cuban sandwich before your flight. Allow 30–45 minutes and roughly $10–20 per person; it’s a casual counter-service stop, handy for a quick bite rather than a long sit-down meal. Check the day’s hours, and leave enough time to collect your luggage if it’s stored elsewhere.
Take a taxi or rideshare from Sandy’s Café to Key West International Airport; the short ride can take longer with traffic, and rental-car return adds another step if you haven’t returned the car already. Follow your rental company’s return instructions, then allow ample time for the return process, airport check-in, and security. Since your flight time isn’t specified, confirm your airline’s recommended arrival window and work backward before deciding how long to spend at the park and café.
No packing list attached yet.