Things to do in Key West, splurging
Hemingway's house, sunset on Mallory Square, a mangrove paddle, dinner at Little Pearl.
This is Key West for people who want the real thing: cortaditos before the crowds, dinners that actually deliver, and cocktail bars with enough history to make the drink taste better. Three days moves you from Old Town treasure museums to Atlantic-facing decks to mangrove wilderness, and the spending is unapologetic throughout.
Day 1: Old Town gold and Gulf sunsets
Start with a sharp Cuban coffee and shipwrecked emeralds, then work through a Mediterranean lunch and the Gulf sunset before a seafood dinner and a Hemingway-haunted nightcap.
- 9:30 AM
- 10:15 AM
Mel Fisher Maritime Museum
Real 1622 Spanish galleon treasure, gold bars, emeralds, and working conservators on site.
Map - 12:30 PM
Azur Restaurant
Neighbourhood Mediterranean on Grinnell Street; take a long lunch on the shaded patio.
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
Hot Tin Roof Restaurant
Waterfront dining room at Ocean Key, steps from Mallory Square, with live music most nights.
Map - 9:30 PM
Captain Tony's Saloon
The original Sloppy Joe's, Hemingway and Tennessee Williams drank here; the lore alone is worth one nightcap.
Map
Day 2: Whitehead Street to the Atlantic
A morning with six-toed cats and Spanish Colonial architecture gives way to tapas and butterflies, then the evening lands at Little Pearl, Key West's finest seafood table, and cocktails over open Atlantic water.
- 9:30 AM
Moondog Cafe
Neighbourhood café a short walk from Little Pearl, start the morning easy with good coffee before heading out.
Map - 10:15 AM
Ernest Hemingway Home and Museum
Hemingway's Spanish Colonial home, six-toed cats roaming the tropical gardens, the essential Old Town cultural stop.
Map - 12:30 PM
Santiago's Bodega
Spanish tapas to share: beef tenderloin, yellowfin ceviche, shrimp and chorizo, sangria.
Map - 2:15 PM
Key West Butterfly and Nature Conservatory
Walk through the climate-controlled glass habitat with 50, 60 butterfly species, flamingos, and exotic birds, a genuinely beautiful afternoon stop.
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
Louie's Backyard - Afterdeck bar
Louie's Backyard Afterdeck: cocktails on a deck over the Atlantic, no reservation needed, the perfect nightcap with Atlantic air.
Map
Day 3: Backcountry paddling and a proper send-off
A guided kayak through mangrove tunnels, a casual marina lunch, a slow botanical wander, and a relaxed resort dinner on the New Town side to close.
- 10:30 AM
Lazy Dog Adventures - backcountry kayaking
Guided two-hour paddle through mangrove tunnels and seagrass flats; watch for rays, small sharks and herons.
Map - 12:30 PM
Hurricane Hole
Casual marina restaurant beside the kayak launch; easy seafood and a cold drink on the water.
Map - 2:30 PM
Key West Tropical Forest and Botanical Garden
Key West Tropical Forest & Botanical Garden, a rare, unhurried wander through the island's only frost-free forest.
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
Marquesa Hotel
The Marquesa is the most considered small hotel in Old Town: restored 1880s houses, two pools, and Day 1 on foot.
Casa Marina Key West, Curio Collection by Hilton
Casa Marina sits on its own stretch of Atlantic beach and puts Louie's Backyard Afterdeck five minutes away on foot, which the itinerary rewards.
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.
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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