Drive or fly
Drive: Miami to Key West is 3.5-4 hours via the Overseas Highway (US-1), the road that crosses 42 bridges over open ocean. The Seven Mile Bridge (the longest, between Marathon and Little Duck Key) is the iconic image — driving across is part of the experience. Stops to budget into the drive: Key Largo (the diving capital), Islamorada (the fishing capital, John Pennekamp Coral Reef State Park), Marathon (the Dolphin Research Center, the Turtle Hospital), Bahia Honda State Park (the best beach in the Keys). Fly: Key West International Airport (EYW) has flights from Miami, Orlando, Tampa, Atlanta, Dallas, and Charlotte. The 50-minute flight from Miami saves 3 hours of driving but you miss the experience that is the road. For 2+ night stays, drive. For 1-night trips, fly.
Duval Street and the historic downtown
Duval Street is the 1.25-mile spine of Old Town Key West — 100+ bars, restaurants, gift shops and historic houses along its length. The most-photographed section runs from Mallory Square (the north end, where the cruise ships dock) to the Southernmost Point Buoy (the south end, the famous red-white-yellow concrete marker that says 'Southernmost Point Continental USA'). Best Duval walks: morning (before the cruise crowd arrives) and evening (after they leave). Key spots: Sloppy Joe's Bar (Hemingway's favourite, the famous Sloppy Joe sandwich), Captain Tony's Saloon (the original Sloppy Joe's location), the Hemingway House at 907 Whitehead, the Truman Little White House.
The Hemingway House
Ernest Hemingway's Key West home (1931-1939) is at 907 Whitehead Street. Tour is $19/adult, runs 30 minutes with a guide, includes the house, his writing studio in the carriage house, the bird-watching pool, and the 60+ descendants of Hemingway's six-toed cat Snow White (the famous polydactyl cats still roam the property). The standout: his writing studio above the carriage house, with the typewriter he used to write 'A Farewell to Arms', 'For Whom the Bell Tolls' (first draft), and 'To Have and Have Not'. The cats are the visitor highlight; for literary travellers, the studio is the moment.
"Key West is two cities. The cruise-day version is Duval Street, the Southernmost Point photo, a beer at Sloppy Joe's. The overnight version is everything else — the sunset sail, the locals' bar at 11 PM, the morning coffee at Cuban Coffee Queen before the crowds arrive."
The Mallory Square sunset celebration
Every evening 90 minutes before sunset, Mallory Square turns into a street performer carnival. Acrobats, fire-jugglers, magicians, sword-swallowers, the cat-trainer (yes), and 200-300 street vendors set up around the square. The sunset itself is good (Gulf-facing) but the experience is the carnival around it. Free, and one of those rare 'tourist traps' that's genuinely worth it. Arrive 90 minutes early for the best viewing spot, bring cash for the buskers (they pass hats — give $5+ if you stop to watch). The whole thing wraps 15 minutes after sunset.
Where to eat
Breakfast: Pepe's Café (the oldest restaurant in Key West, 1909, the eggs Benedict), Five Brothers Grocery (the Cuban coffee and ham-egg-cheese on Cuban bread — Cuban breakfast for $7). Lunch: B.O.'s Fish Wagon (the conch fritters, the fish sandwich, the open-air shack atmosphere), Mr. Z's Pizzeria (the New York-style slice, the line is the recommendation). Dinner: Latitudes Restaurant at Sunset Key (boat-shuttle dinner on a private island, $$$$, the sunset reservation), Better Than Sex (dessert restaurant — yes, the name is the whole thing, the chocolate-dipped wine glass rims), Hot Tin Roof at the Ocean Key Resort (the Floribbean menu, sunset patio). Avoid: any Duval Street restaurant with a server outside trying to wave you in.
Day-trip from Key West
Dry Tortugas National Park: 70 miles west of Key West, accessible only by Yankee Freedom III ferry (3.5 hours each way, full-day trip, $200-220/person includes lunch) or seaplane (40 minutes each way, $375/person). The destination is Fort Jefferson (a remote 19th-century coastal fortress) plus the best snorkelling in the continental US (the reef is 100 feet off the beach, no boat required). One of the best day-trip experiences in Florida. Book 30+ days ahead — the ferry sells out for most peak-season departures.
When to come
Best: November through April — temperatures 70-82°F, humidity manageable, no mosquitoes, lowest hurricane risk. December-March is high season with peak rates. Summer (June-September) is hot and humid, with afternoon thunderstorms; hotel rates drop 30-40% but the experience suffers. Hurricane risk peaks August-October — Hurricane Irma (2017) hit Key West directly; book cancellable rates. Key West Fantasy Fest (late October) and Hemingway Days Festival (mid-July) are the two signature events; hotel rates spike for both.
Where to stay
Boutique splurge: The Marquesa Hotel (1884 Victorian, four buildings around a pool, restaurant Café Marquesa, $399-679/night), Ocean Key Resort & Spa (Mallory Square location, $329-549, the Sunset Pier room category). Mid-range: The Gardens Hotel (boutique, in-house garden bar, $279-449), Marriott Key West Beachside Resort (one of the few proper-beach hotels, $349-549). Budget: The Cypress House (Old Town B&B, $189-269), Best Western Key Ambassador Inn (modest, on the Boulevard side away from Old Town, $159-229). Avoid: the chain hotels on US-1 north of the airport unless you have a rental car — they're 15-20 minutes from Old Town.
