Key West, Florida
Key West for Grown-Ups: Things to Do for Adults
Key West is at its best when you skip the Duval Street bar crawl: a sunset sail with a glass of champagne, dinner on a private island, Hemingway's house and cats, a proper live-music bar and a cabaret. Here's the grown-up version of the island.
- Best base
- Old Town, within walking distance of the waterfront
- Ideal stay
- 3 to 4 nights
- Book ahead
- The Dry Tortugas ferry, a sunset sail, Latitudes, Louie's Backyard, Café Marquesa
- Good to know
- Old Town is small and flat: walk or rent a bike, and leave the car at the hotel
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.
Itineraries and guides
Start with the 3-day Key West itinerary, or our Key West weekend itinerary for two days. Couples should read things to do in Key West for couples. Driving down from the mainland? Spend a couple of nights in Miami first.
Grown-up essentials
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.
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.
Ernest Hemingway Home & Museum
907 Whitehead St
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.
The Green Parrot
601 Whitehead St
"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).
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.
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.
Sunset, three ways
Sunset is the island's main event. Watch it with the crowd and the street performers at Mallory Square, from a table at Sunset Pier next door, or out on the water on a schooner sail. For something quieter, the beach at Fort Zachary Taylor faces the same way.
Sunset Celebration at Mallory Square
Mallory Square, 400 Wall St
Key West's nightly ritual since the late 1960s: jugglers, magicians, musicians, artists and food stalls on the square while the sun drops into the Gulf. Free.
Tip: Arrive 45 minutes before sunset for a spot on the water's edge.
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.
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.
Worth knowing
- Winter and spring are high season, with the best weather and the highest prices. September and October are quiet, but it's hurricane season and some places close for a break (Blue Heaven is closed until October 15, 2026).
- Duval Street gets loud after dark. Whitehead Street, Bahama Village and the upper end of Duval are calmer.
- Better Than Sex is closed Mondays and Tuesdays, so plan a dessert night later in the week.
- The Dry Tortugas ferry leaves at 8 a.m. and takes the whole day. Book it early in your trip so you have a spare day if the weather cancels it.
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 there to do in Key West for adults?
A schooner sunset sail with wine, dinner on Sunset Key at Latitudes or on the water at Louie's Backyard, the Hemingway Home and the lighthouse, live bands at the Green Parrot, a cabaret at La Te Da, dessert at Better Than Sex and a day trip to the Dry Tortugas.
Is Key West just a party town?
Only on Duval Street at night. The rest of the island is quiet, historic and walkable, with very good restaurants, museums and sunset sails that suit grown-ups.
How many days do you need in Key West?
Three or four. Three covers Old Town, the waterfront and a sunset sail; a fourth lets you take the all-day ferry to the Dry Tortugas.