Key West · 3-day itinerary
3 Days in Key West: A Grown-Up Itinerary
Three days in Key West gives you one day in Old Town, one day out at the Dry Tortugas and one on the water and at the beach, with a sunset and a very good dinner every evening.
- Day 1
- Hemingway Home, the lighthouse, Mallory Square sunset, Café Marquesa, the Green Parrot
- Day 2
- The Dry Tortugas by ferry, then Santiago's Bodega and La Te Da
- Day 3
- Fort Zachary Taylor, a sunset sail, dinner at Latitudes
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Day 1: Old Town
Everything today is walkable.
Morning
Ernest Hemingway Home & Museum
907 Whitehead St
Take the guided tour, then wander the gardens and meet the cats.
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.
Late morning
Key West Lighthouse & Keeper's Quarters
938 Whitehead St
Across the street: climb the 88 steps for the view.
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.
Sunset
Sunset Celebration at Mallory Square
Mallory Square, 400 Wall St
Street performers and the sun going down over the Gulf.
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.
Dinner
Café Marquesa
The Marquesa Hotel, 600 Fleming St
A quiet, polished dinner 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.
Late
The Green Parrot
601 Whitehead St
Live bands and a local crowd.
"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: The Dry Tortugas
An early start and a long, spectacular day at sea.
Day
Dry Tortugas National Park by ferry
Yankee Freedom ferry, 100 Grinnell St
Check in at 7 a.m. Snorkel gear, the park fee and a guided fort tour are included.
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.
Dinner
Santiago's Bodega
207 Petronia St, Bahama Village
Easy tapas and sangria after a long day.
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.
Evening
La Te Da
1125 Duval St
A cabaret or the piano bar at the quiet end of Duval.
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.
Day 3: Beach, sail and Sunset Key
A slow morning, then the best evening of the trip.
Morning
Fort Zachary Taylor Historic State Park
End of Southard St, Truman Annex
The fort, then a swim and a lie on the beach.
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.
Afternoon
Harry S. Truman Little White House
111 Front St, Truman Annex
The guided tour of Truman's winter White House.
Florida's only presidential museum: Truman's winter White House on the old naval station, seen on a guided tour that also covers Eisenhower's and Edison's stays. Open daily 9:30 a.m. to 5 p.m.
Sunset
Danger Charters Wind & Wine Sunset Sail
Old Town waterfront (departure point on booking)
Two hours on a schooner with wine and champagne.
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
Latitudes on Sunset Key
Sunset Key; launch from 245 Front St
The short boat ride to Sunset Key for dinner on the beach.
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.
Swaps
- Rather not spend a day at sea? Swap day 2 for a drive up to Bahia Honda State Park and its beaches.
- Want an Atlantic view with lunch? Swap day 3's afternoon for Louie's Backyard and a drink on the Afterdeck.
- Sweet tooth? End any evening from Wednesday to Sunday at Better Than Sex.
Bahia Honda State Park
36850 Overseas Hwy, Big Pine Key (about 45 minutes)
Three beaches, Sandspur, Loggerhead and Calusa, with soft sand and clear water, an easy drive up the Overseas Highway. Open 8 a.m. to sundown.
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.
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.
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 3 days in Key West enough?
Yes. It covers Old Town, the waterfront, a sunset sail and a full-day trip to the Dry Tortugas, at a relaxed pace.
Do you need a car in Key West?
No. Old Town is small and flat, so walk or rent a bike. You only need a car to drive up the Keys to places like Bahia Honda.
When is the best time to visit Key West?
December to May for dry, warm weather, though it's the busiest and priciest time. Late spring and early December are a good balance.