Key West Travel Guide
Key West for First-Timers
Everything a first visit needs before the itinerary — flying versus driving the Overseas Highway, why you should ditch the car, bikes and the free Duval Loop, the must-dos versus the skippables, and the island's unwritten rules.
Key West is small, flat, and easy — about four miles long and two wide, with the historic Old Town packed into its western half — but first-timers still make the same handful of mistakes: bringing a car into Old Town, booking the wrong part of the island, missing the boat trips that sell out, and spending every evening in the same three bars. This guide is the briefing before the itinerary.
Getting here: fly or drive. Key West International Airport sits on the island's eastern side, a short cab ride from Old Town, and its new terminal opened in 2025. Nonstop flights are limited and often pricier than flying into Miami or Fort Lauderdale, which is why so many visitors choose the drive: roughly 160 miles from Miami down the Overseas Highway, across 42 bridges, including the Seven Mile Bridge. Allow three and a half to four hours without stops, more on Friday afternoons and holiday weekends, and do not rush it — the drive is part of the trip. Stop for a swim at Bahia Honda State Park, about an hour short of Key West, and you arrive with the right pace already set. Ferries from the Gulf coast and cruise ships are the other ways in; cruise passengers get a single day and should prioritize ruthlessly.
Ditch the car. If you drive down, park the car at your hotel and leave it there. Old Town's streets are narrow, parking is scarce and expensive, and nothing in the historic district is more than a half-hour walk from anything else. Bicycles are the island's real transport — most hotels rent or lend them, and rental shops are everywhere; lock them every time. The City of Key West runs the free Duval Loop bus around Old Town, the Old Town Trolley offers hop-on hop-off service, and cabs and electric carts fill the gaps. You only need wheels again for day trips up the Keys.
Where to base yourself. Old Town is the answer for nearly every first visit: the Mallory Square and harbor end of Duval for maximum convenience and nightlife, the Historic Seaport for boat trips and a slightly calmer harbor scene, mid-Duval side streets for boutique charm, and the south end of Duval for beach resorts and family pools. Casa Marina's south-shore district is a mile from Duval but has the best beach. Stock Island, next door, is the value play with a car. Our where-to-stay guide breaks it down in detail.
The must-dos. Five experiences define a first visit. Sunset Celebration at Mallory Square, free every night and the island's heartbeat. The Hemingway Home and its six-toed cats, best first thing in the morning. A day on the water — either a reef snorkel trip on North America's only living coral barrier reef or, if you have one full day to give, the ferry or seaplane to Dry Tortugas National Park and Fort Jefferson, the most remarkable day trip in Florida. A walk down Duval Street from the Gulf to the Atlantic. And the Southernmost Point photo — currently at the full-size replica buoy at the foot of Duval while the original's seawall is rebuilt. Add the lighthouse climb, the Truman Little White House, and Fort Zachary Taylor's beach as your schedule allows.
Book these ahead. The Dry Tortugas ferry and seaplane sell out weeks ahead in winter and spring — book as soon as your dates are firm. Reef trips and sunset sails are easier but fill on holiday weeks. Hotels for Fantasy Fest in late October, Christmas and New Year, and the spring-break weeks book months out. Everything else — the museums, the Conch Train, the Butterfly Conservatory — can be booked a day or two ahead or on arrival, though advance tickets skip the lines on cruise-ship days.
Cruise-ship days. Several days a week, one or more large ships dock at Key West, and from mid-morning to late afternoon Old Town's main sights get crowded. Check the port schedule, then do the Hemingway Home, the lighthouse, and the Southernmost Point early, and spend the busy middle of the day on the water, at Fort Zach, or by the pool. The crowds thin before sunset.
The unwritten rules. Tip the street performers and bar musicians — they live on it. Do not feed or chase the free-roaming chickens and roosters; they are a protected part of island life and they will wake you at dawn regardless. Wear reef-safe sunscreen and never touch the coral. Respect the residential quiet of the side streets late at night; real people live in those conch houses. Dress is casual everywhere — shorts and sandals are fine almost anywhere. And slow down: Key West punishes over-scheduling and rewards the long lunch, the porch, and the extra sunset.
Weather and season. Winter and spring are high season, with warm, dry days and the highest prices. Summer is hot, humid, and stormy in the afternoons but cheaper, with the calmest seas for boat trips. Hurricane season runs from June through November, peaking from August to October; travel insurance and flexible bookings are wise then. Our when-to-go guide has the full calendar.
How long to stay. Two nights covers the essentials at a sprint. Three or four nights is the sweet spot, giving you a full day for Dry Tortugas, a water day, two museum mornings, and nightly sunsets. A week lets you add Bahia Honda, the Lower Keys, and the art of doing nothing — which, in Key West, counts as an activity.