Key West 3-Day Itinerary
The perfect long weekend in Key West: 3 days and 2 nights for about $1,814 for two, flights from New York included (estimate).
Three days of must-see attractions, local favorites, and insider tips, with what the weekend costs from where you fly.
What 3 days, 2 nights costs
The fare from where you fly, two nights at the typical hotel night and three days of spend. Change it to fit your trip.
- Fare · New York to Key West × 2Economy round trip, usually about $522 eachPricier than every one of the 10 days we checked fares on this route, by our own fare checks since Jul 2026. How we know$1,044
- Hotel night (estimate) · $160 × 2 nightsOur city guide's estimate: we don't check Key West hotel prices ourselves yet. 2 travellers share a room.$320
- Daily spend · $75 × 2 travellers × 3 daysRestaurants, transport and paid sights, per person per day. The hotel isn't in it.$450
3 days, 2 nights, 2 travellers, mid-range, flying from New York. The hotel night is our guide's estimate; the rest are usual prices we track. Not a price you can book.
How we know
- Fare: the middle price of the economy round trips we found from New York on our latest check (half were cheaper, half dearer), for departures in the coming weeks.
- Hotel night: our city guide's estimate, because we don't check Key West hotel prices ourselves yet.
- Daily spend: food, local transport and sights per person, from our city guide, by travel style. The hotel isn't in it.
- Total: fare × travellers + hotel night × nights × rooms + daily spend × travellers × days. Prices move, so treat it as a guide, not a quote.
Trip overview
- Duration
- 3days 2nights
- Best time
- November to April
Day by day
Each day's highlights in order. Want more days or a different pace? The planner at the end reshapes it around you.
Day 1Duval Street
- Hemingway Home
- Southernmost Point marker
- Sloppy Joe's Bar
Day 2Mallory Square sunset
- snorkeling at Fort Zachary Taylor
- Key lime pie crawl
Day 3Dry Tortugas National Park day trip via Yankee Freedom ferry
- sunset cocktails
Add these if you have a spare evening
Verified spots in Key West that the classic route skips.
- Hidden GemsThe Key West Butterfly and Nature Conservatory
Step inside a glass-enclosed tropical habitat where hundreds of live butterflies from around the world flutter freely past cascading waterfalls and rare flowering plants.
- Hidden GemsKey West Gardens at Fort West Martello
This crumbling Civil War-era fort tucked beside Higgs Beach has been lovingly reclaimed by the Key West Garden Club, filling its ruined ramparts with a secret jungle garden.
- Hidden GemsKey West Lighthouse
Climb the 88 steps of this 1848 lighthouse for a sweeping panoramic view of the island and browse the restored keeper's cottage filled with maritime artifacts below.
- Hidden GemsSmathers Beach
Key West's longest public beach stretches along South Roosevelt Boulevard, drawing locals at sunrise for calm shallow waters and beachside vendors renting kayaks and paddleboards.
- Fine DiningNine One Five
Occupying a gorgeous wraparound porch at 915 Duval Street, this restaurant serves shareable small plates and inventive cocktails in an atmosphere that perfectly balances romance and revelry.
- Fine DiningLouie's Backyard
Perched directly over the Atlantic on a series of open-air decks, Louie's Backyard serves refined Caribbean-inspired cuisine with one of the most breathtaking oceanfront settings in the Keys.
Each place was checked on Google Maps: real address, right city, still open.
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