Key West · Romantic getaway
A Romantic Getaway to Key West: Plan It Like a Grown-Up
A romantic trip to Key West is easy to get right and easy to get wrong. Stay on the wrong street and you'll hear Duval until 2 a.m.; book the sunset sail on your last night and the weather can take it away. This is how we'd plan three nights for two: when to come, where to sleep and what to book before you leave home.
- How long
- 3 nights; 4 with the Dry Tortugas
- When
- Winter and spring for the weather; September and October are quieter but hurricane season
- Where to stay
- An Old Town guesthouse on a side street, not on Duval
- Book first
- A sunset sail, Latitudes, Louie's Backyard, Café Marquesa
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.
Before you book
Winter and spring are high season, with the best weather and the highest prices. September and October are quiet and cheaper, but it's hurricane season and some places close for a break, so check before you fix dates. Old Town is small and flat: walk or rent bikes, and leave the car at the hotel. Pick a guesthouse on a quiet Old Town street, or a waterfront resort near Mallory Square, and you can walk to every sunset and dinner on this page.
Three nights for two
Night 1: Sunset on the water
Put the sail first, so there's time to rebook if the wind or rain cancels it.
Afternoon
Ernest Hemingway Home & Museum
907 Whitehead St
Guided tours every 15 minutes; the six-toed cats are asleep in the garden.
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.
Sunset
Danger Charters Wind & Wine Sunset Sail
Old Town waterfront (departure point on booking)
Two hours on a classic schooner with wine, champagne and a cheese and chocolate spread.
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
Café Marquesa
The Marquesa Hotel, 600 Fleming St
A quiet, polished dining room a block off Duval.
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.
Night 2: An island dinner
A slow day, then the most romantic table in town.
Morning
Key West Lighthouse & Keeper's Quarters
938 Whitehead St
88 steps for the view over the rooftops, before it gets hot.
Climb 88 steps for one of the best views over the island's rooftops and turquoise water, then look round the keeper's house. Open daily 10 a.m. to 5 p.m.; it's across the street from the Hemingway Home.
Afternoon
Fort Zachary Taylor Historic State Park
End of Southard St, Truman Annex
Beach and shade at the old fort; the fort itself closes at 5.
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.
Dinner
Latitudes on Sunset Key
Sunset Key; launch from 245 Front St
Book an early table so you cross to Sunset Key in daylight.
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.
Night 3: Sunset Pier and a late dessert
The classic sunset, without the crowd.
Afternoon
Key West Butterfly & Nature Conservatory
1316 Duval St
Butterflies flying free under a glass dome, and the two resident 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 the same view as Mallory Square, from a table.
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
Louie's Backyard
700 Waddell Ave
Waterfront tables on the Atlantic side; the Afterdeck Bar is below.
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.
Late
Better Than Sex
926 Simonton St
Dessert and cocktails, Wednesday to Sunday only.
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.
Add a fourth day
With a fourth day, take the high-speed ferry 70 miles west to Fort Jefferson in Dry Tortugas National Park. Check-in is at 7 a.m. and you're back about 5:15 p.m., with the fort tour, snorkel gear and park fee included. Book it early in the trip so you have a spare day if the weather cancels it. Or for a night out instead, the cabaret at La Te Da has live entertainment in the piano bar nightly from 8:30 p.m.
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.
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.
Our advice
- Book the sunset sail and Latitudes before you fly. They are the two things that sell out.
- Better Than Sex is closed Mondays and Tuesdays: if you arrive at the start of the week, move dessert night later.
- Duval Street gets loud after dark. Whitehead Street, Bahama Village and the upper end of Duval are calmer.
- Check current hours, sailing times and prices before you go.
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 Key West good for a romantic getaway?
Yes. Old Town is small, walkable and quiet away from Duval Street, with sunset sails, candlelit restaurants and waterfront dinners. Three nights is enough for a couple's trip.
How many nights do you need for a romantic Key West trip?
Three nights covers a sunset sail, dinner on Sunset Key and an evening at Sunset Pier. Add a fourth for the all-day ferry to the Dry Tortugas.
When is the best time for a romantic trip to Key West?
Winter and spring have the best weather but the highest prices. September and October are quieter and cheaper, but it's hurricane season and some places close for a break.
Where should couples stay in Key West?
In Old Town, in a guesthouse on a quiet side street or a waterfront resort near Mallory Square, so sunsets and dinners are on foot.