Key West · For couples
Things to Do in Key West for Couples
Warm nights, sunsets over the water and small, candlelit restaurants: Key West is one of the easiest romantic trips in the US. Here's how to plan it.
Some links on this page go to booking partners. If we join their affiliate programmes we may earn a commission when you book, at no extra cost to you. It never decides what we recommend. How we make money.
Dinner for two
Latitudes on Sunset Key
Sunset Key; launch from 245 Front St
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.
Tip: Book an early dinner so the boat ride over is in daylight.
Louie's Backyard
700 Waddell Ave
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.
Tip: Come for a drink on the Afterdeck even if you eat elsewhere.
Café Marquesa
The Marquesa Hotel, 600 Fleming St
An intimate hotel dining room a block off Duval, with a seasonal menu from chef Travis Lee and polished service. Dinner nightly from 5:30 p.m.
Hot Tin Roof
Ocean Key Resort, 0 Duval St
The Ocean Key Resort's waterfront dining room at the foot of Duval Street, serving seafood-led dinners daily from 6 p.m. It holds a 2026 Wine Spectator Award of Excellence.
Sunset and after dark
Danger Charters Wind & Wine Sunset Sail
Old Town waterfront (departure point on booking)
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.
Sunset Pier
Ocean Key Resort, 0 Duval St
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.
Better Than Sex
926 Simonton St
An adults-only dessert-and-cocktail room with red velvet curtains, low light and just 20 tables. Open Wednesday to Sunday, 6 to 11 p.m.; closed Mondays and Tuesdays.
Tip: Book at weekends. It works as a nightcap after dinner elsewhere.
La Te Da
1125 Duval St
A guesthouse, restaurant and cabaret at the quiet end of Duval. Randy Roberts sings (live, no lip-syncing) as Cher, Liza and Bette, and the piano bar has live entertainment nightly from 8:30 p.m.
By day
Dry Tortugas National Park by ferry
Yankee Freedom ferry, 100 Grinnell St
A high-speed catamaran 70 miles west to Fort Jefferson, a vast brick fort on a speck of sand, with a guided fort tour, snorkel gear and the park entrance fee included. Check-in 7 a.m., back about 5:15 p.m.
Tip: Book weeks ahead in winter and spring; the boat has limited seats.
Fort Zachary Taylor Historic State Park
End of Southard St, Truman Annex
A 19th-century brick fort with a beach, picnic shade and a quieter sunset spot than Mallory Square. Open 8 a.m. to sundown; the fort itself closes at 5 p.m.
Key West Butterfly & Nature Conservatory
1316 Duval St
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.
Our advice
- Book the sunset sail for your first or second evening, so there's time to rebook if the weather turns.
- Reserve Latitudes for an early dinner so you cross to Sunset Key in daylight.
- Stay in a guesthouse on a quiet Old Town street rather than on Duval.
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
What is the most romantic thing to do in Key West?
A schooner sunset sail with wine and champagne, followed by dinner on the beach at Latitudes on Sunset Key.
Where should couples eat in Key West?
Latitudes on Sunset Key or Louie's Backyard for dinner by the water; Café Marquesa for a quiet, polished evening; Santiago's Bodega for relaxed tapas.
What do couples do in Key West at night?
Watch the sunset from a boat or Sunset Pier, have dinner in Old Town, then catch the cabaret at La Te Da or share dessert at Better Than Sex (Wednesday to Sunday).