Things to do in Key West
Old Town dives, shipwreck gold, mangrove kayaks, and one great fish sandwich.
This is Key West at the right pace: mornings with strong Cuban coffee, afternoons split between history and the water, evenings that drift from a proper dinner into a barstool at a saloon that's been open since before your grandparents were born. It suits travellers who want the real texture of the island without paying resort prices for every meal, and who are happy to walk almost everywhere.
Day 1: Old Town, Gold and a Proper Dive
A day that moves from shipwreck treasure and a gravel-lot fish sandwich to a sunset on the Gulf and a nightcap at the bar where Hemingway actually drank.
- 9:30 AM
Cuban Coffee Queen
Strong Cuban coffee and pastries from a locals' favourite, the perfect launchpad.
Map - 10:15 AM
Mel Fisher Maritime Museum
Real 1622 Spanish shipwreck gold, silver and emeralds, conservators work on artifacts in the open, wildly underrated.
Map - 12:30 PM
B.O.'s Fish Wagon
Funky open-air fish shack beloved by locals, fried fish sandwich on a gravel lot, zero pretension.
Map - 6:00 PM
Sunset Celebration at Mallory Square
Come about two hours before sunset for jugglers and musicians, then watch the sun drop into the Gulf.
Map - 7:30 PM
Cafe Marquesa
Intimate dining room in the Marquesa Hotel, a block off Duval; the trip's proper sit-down dinner.
Map - 9:30 PM
Captain Tony's Saloon
Original Sloppy Joe's location dripping with Hemingway and Tennessee Williams lore, a proper historic dive for a nightcap.
Map
Day 2: Hemingway, Tapas and the Green Parrot
Old Town on foot: the Spanish Colonial house with its six-toed cats, a lazy tapas lunch, butterflies in the afternoon, and one of Florida's best live-music saloons to close it out.
- 9:30 AM
- 10:15 AM
Ernest Hemingway Home and Museum
Hemingway's Spanish Colonial home, with tropical gardens and dozens of six-toed cats; join a guided tour.
Map - 12:30 PM
Santiago's Bodega
Spanish tapas to share: beef tenderloin, yellowfin ceviche, shrimp and chorizo, sangria.
Map - 2:30 PM
Key West Butterfly and Nature Conservatory
Walk into the glass butterfly habitat, 50 to 60 species plus flamingos and exotic birds, a genuinely surprising afternoon.
Map - 7:30 PM
Little Pearl
Small Old Town seafood room at Olivia and Elizabeth; book ahead and order the day's catch.
Map - 9:30 PM
Green Parrot
Saloon open since 1890 with free popcorn and some of Florida's best live music, the perfect unpretentious nightcap.
Map
Day 3: Water, Mangroves and the West End
The island's quieter side: a shady botanical garden, a raw bar on the water, two hours paddling mangrove tunnels, and a late walk at the nature preserve before a seafood dinner.
- 10:30 AM
Key West Tropical Forest and Botanical Garden
Native hardwood forest and freshwater ponds on Stock Island; open 10 to 4, $15 for adults.
Map - 12:30 PM
The Docks Restaurant + Raw Bar
Fresh seafood and raw bar right on the water, casual, well-rated, and great value for lunch.
Map - 2:30 PM
Lazy Dog Adventures - backcountry kayaking
Guided 2-hour kayak through mangrove tunnels and seagrass flats in the Wildlife Refuge, the adventure locals swear by.
Map - 4:30 PM
The Key West Nature Preserve
Short boardwalk through salt ponds and buttonwoods to a quiet stretch of Atlantic shore.
Map - 7:30 PM
Tavern N Town
Resort dining room off the Beachside lobby; steaks, seafood and tapas without the drive back to Old Town.
Map
Where to stay
Eden House
A classic Old Town guesthouse two blocks from the Day 1 and Day 2 action, with the kind of laid-back character that fits this trip perfectly.
La Concha Key West, Autograph Collection
Dead centre on Duval Street, walking distance to Captain Tony's and the Green Parrot, and a reliable mid-range base without the resort markup.
Make Key West your trip
Swearby drafts the days from places people swear by. Swap any stop, then invite the crew by text, even friends without the app. Vote on dates, track costs as you go, and everyone gets one number at the end.
Get Swearby on the App StoreBefore you go
Book ahead
- Key West Food Tours Southernmost Food Tasting & Cultural Walking Tour: a few days ahead
- Dry Tortugas National Park: months ahead
- Reef Snorkelling with Fury or Sebago, Key West: a few days ahead
- Sunset Sail, Key West: a few days ahead
- Key West Fishing Charter, Charter Boat Row: weeks ahead
- Sandbar Charter, Key West Backcountry: weeks ahead
Skip these
- Duval restaurants with barkers, photo menus and 2 for 1 boards. Eat a block off Duval, in Bahama Village, on Truman or on Stock Island.
- The Southernmost Buoy at midday means a long photo queue. Go before 9am. Avoid timeshare pitches sold as free sunset cruises.
- Key West beaches are narrow and rocky over coral. Bring water shoes and take a boat for the best swimming, or drive to Bahia Honda.
The full Key West travel guide: when to go, safety, getting around