🏖️ Key West, FL Travel Guide
Key West Vacation Guide
Welcome to NME’s Key West travel guide. Florida’s southernmost island city — historic Old Town guesthouses, Duval Street nightlife, coral-reef snorkeling, and sunset celebrations, all mapped out by category so you can plan your trip around what you actually want to do.
🏆 59 Attractions
🍲 52 Restaurants
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Hotels
72 verified hotels and guesthouses across Duval Street, Truman Annex, beachfront resorts, and Key West’s famous historic inns.
Things to Do
59 verified attractions — historic sites, snorkeling and diving, sunset sails, and Dry Tortugas National Park day trips.
Restaurants
52 verified restaurants — Duval Street icons, waterfront seafood, fine dining, and Cuban favorites.
Getting to Know the Area
Duval Street
Truman Annex
Historic Seaport
Bahama Village
New Town
Key West is a tiny island, about four miles long and one mile wide, so nearly everything is walkable or a short bike ride from Old Town. Duval Street runs the length of the historic district and anchors most of the nightlife and shopping; Truman Annex and the Historic Seaport sit at its western end near Mallory Square, home to the nightly sunset celebration. Bahama Village, just off lower Duval, has a quieter, more local feel, while New Town toward the airport holds most of the beachfront resorts and chain hotels.
Planning Tips
- Fly into Key West or drive the Overseas Highway. Key West International Airport has direct flights from several major cities, or you can drive the scenic Overseas Highway (US-1) down from Miami, about 3.5-4 hours.
- Old Town’s historic guesthouses book up fast for events. Fantasy Fest (late October) and Pride (June) sell out small-room-count guesthouses months in advance.
- You mostly don’t need a car in Old Town. Bikes, scooters, and walking cover nearly everything — a car mainly matters for day trips or reaching Stock Island.
- Afternoon showers are common in summer. Key West’s rainy season runs roughly June through October — plan reef trips and outdoor activities for mornings when possible.
📅 2026 Theme Weeks
Key West’s small-island calendar swings between literary, culinary, and costume-driven festivals almost every month, with a few signature weeks worth planning a trip around — or avoiding, depending on your tolerance for crowds.
❄️ Winter Focus Weeks (January – February)
- Key West Literary Seminar (January 8–11, 2026): A four-day gathering of authors and readers at the San Carlos Institute and other Old Town venues.
- Key West Food & Wine Festival (Jan 28–Feb 1, 2026): A five-day culinary festival with tastings, chef dinners, and a Grand Tasting Village on the waterfront.
🌸 Spring Theme Weeks (March – May)
- Conch Republic Independence Celebration (April 17–26, 2026): A ten-day, tongue-in-cheek commemoration of Key West’s 1982 mock secession, with a bed race and mock naval battle.
- Key West Songwriters Festival (Apr 29–May 3, 2026): Five days of original songwriter performances by Nashville and pop hitmakers in bars and venues across the island.
☀️ Summer Peak Weeks (June – August)
- Hemingway Days (July 21–26, 2026): A week honoring Ernest Hemingway’s Key West years, capped by the Hemingway Look-Alike Contest at Sloppy Joe’s Bar.
- Key West Lobsterfest (August 5–9, 2026): A Duval Street food festival celebrating the opening of spiny lobster season.
🍁 Fall Focus Weeks (September – October)
- Fantasy Fest (October 16–25, 2026): Key West’s signature adults-oriented costume festival — ten days of parades, body painting, and a masquerade march down Duval Street.
🎄 Holiday Theme Weeks (November – December)
- Key West New Year’s Eve Drops (December 31, 2026): Duval Street’s rival midnight countdowns, including the Sunset Pier pirate wench drop and the giant conch shell drop.
How many days should I plan for a Key West trip?
3-4 days covers the main sights comfortably — Old Town, a sunset sail, and a snorkeling trip — while 5+ days lets you add a full-day Dry Tortugas National Park excursion, which is worth building real time around.
Do I need a car in Key West?
Not for Old Town itself — most hotels, restaurants, and attractions are walkable or a short bike ride apart. A car (or the Overseas Highway drive down) is mainly useful for exploring beyond the island or reaching the airport.
What’s the best time of year to visit Key West?
Late spring (April-May) and fall (October-November, after hurricane season calms down) tend to have good weather with lower crowds and prices than the busy winter high season.
