Key West · Weekend itinerary
A Weekend in Key West for Grown-Ups
Two days is enough for the classic Key West weekend: Old Town and the waterfront by day, two sunsets, two very good dinners and a night of live music.
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Day 1: Old Town and a sunset sail
History in the morning, the water in the evening.
Morning
Ernest Hemingway Home & Museum
907 Whitehead St
Tours start every 15 minutes from 9:15 a.m.
The 1851 house Hemingway bought in 1931, shown on 20 to 30-minute guided tours every 15 minutes, with the famous six-toed cats asleep in the gardens. Open daily 9 a.m. to 5 p.m.; tickets at the gate.
Lunch
Louie's Backyard
700 Waddell Ave
Lunch by the Atlantic; book ahead.
Waterfront tables on the Atlantic side of the island, with island cooking and the Afterdeck Bar on the water below, open from 11:30 a.m. until late. Lunch and dinner daily; reservations strongly recommended.
Sunset
Danger Charters Wind & Wine Sunset Sail
Old Town waterfront (departure point on booking)
Wine and champagne on a schooner.
A two-hour sunset sail on a classic schooner for up to 26 guests (ages 13+), with eight wines including champagne, craft beer and a spread of cheese, charcuterie and chocolate. Calmer and smaller than the party boats.
Dinner
Santiago's Bodega
207 Petronia St, Bahama Village
Tapas in Bahama Village.
Tapas, sangria and a good wine list in a quirky Bahama Village cottage of mismatched chairs and reclaimed wood. Shared plates suit two people well.
Late
The Green Parrot
601 Whitehead St
The island's best live-music bar.
"A sunny place for shady people": a corner bar on Whitehead Street with live bands, a well-worn pool-hall feel and a history going back to 1890. Open daily from 10 a.m. until 2 a.m. (4 a.m. at weekends).
Day 2: Treasure, butterflies and Sunset Key
An easy day, ending with the most romantic dinner on the island.
Morning
Mel Fisher Maritime Museum
200 Greene St
Spanish treasure from the 1622 fleet.
Treasure raised from the Atocha and the rest of the 1622 Spanish fleet, plus a conservation lab you can tour on weekdays and weekend afternoons. Open daily 10 a.m. to 4 p.m.
Afternoon
Key West Butterfly & Nature Conservatory
1316 Duval St
The glass dome, the butterflies and the flamingos.
A glass-domed tropical garden with 50 to 60 species of butterfly flying free and two resident flamingos, Rhett and Scarlett. Open daily 9 a.m. to 5 p.m.
Sunset
Sunset Pier
Ocean Key Resort, 0 Duval St
Live music and a drink over the water.
An open-air pier bar next to Mallory Square with live music every evening and a clear view of the sunset without the crowd on the square. Open daily 11:30 a.m. to 8:30 p.m., weather permitting; no reservations.
Dinner
Latitudes on Sunset Key
Sunset Key; launch from 245 Front St
Take the boat over to Sunset Key.
A beachfront restaurant on the small private island of Sunset Key, reached by a short boat ride from the Front Street marina. Dinner nightly from 5 p.m.; OpenTable named it one of the 100 most romantic restaurants in the US in 2025.
Staying longer? Our 3-day Key West itinerary adds the Dry Tortugas.
Everything here was checked in September 2026. Key West hours shift with the seasons and hurricane season runs June to November, so confirm before you go.
Questions people ask
Is a weekend enough for Key West?
Yes, for Old Town, a sunset sail and two good dinners. Add a day for the Dry Tortugas.
What should you not miss in Key West?
A sunset, from Mallory Square or on the water; the Hemingway Home; a night at the Green Parrot; and dinner by the sea at Louie's Backyard or Latitudes.