Base: Old Town, all three nights. Today is on foot along Whitehead Street, the spine of the old town, from the Hemingway Home to Mallory Square, about a mile end to end. The Hemingway Home is open daily 9 a.m. to 5 p.m. at about $19 per adult; the lighthouse across the street opens 10 a.m. to 5 p.m. at about $17. Pace: easy and flat; a morning of two houses, a long lunch and a rest in the room, then out again for sunset.
The Ernest Hemingway Home and Museum
Start at 907 Whitehead Street when the gates open at 9 a.m. Hemingway lived and wrote in this Spanish-colonial limestone house in the 1930s, and his writing studio still stands across the courtyard above the old carriage house. The grounds are home to about 60 cats, many of them polydactyl, with six toes, descended from a cat the family was given.
Tickets are sold at the gate only, with no reservations, about $19 per adult. Staff give a 20 to 30 minute talk through the house about every 15 minutes, starting at 9:15; after it, wander the gardens and the pool at your own pace. Allow about 1½ hours.
Expert tip: be at the gate before 9:15 to join the first house talk, because by late morning the cruise-ship crowds arrive and the rooms fill shoulder to shoulder.
The Key West Lighthouse and Keeper’s Quarters
Cross the street to the lighthouse at 938 Whitehead Street. It was built in 1847 after a hurricane destroyed the first one, and it lit the way for ships until 1969. Climb the 88 steps to the top for a wide view over Old Town’s tin roofs to the sea, then walk through the keeper’s quarters, set up as the family home it was.
It opens at 10 a.m., last admission 4:30 p.m., about $17 per adult at the door and a little less online. Allow about an hour, and climb before noon while the stairwell is still cool.
Bahama Village and the Southernmost Point
Where to eat: walk west into Bahama Village, the old neighborhood of Bahamian settlers around Petronia Street, for a long lunch in a garden courtyard; Blue Heaven, with its roosters and Key lime pie, is the best known.
Then walk to the corner of Whitehead and South Streets for the striped concrete buoy that marks the southernmost point of the continental United States, about 90 miles from Cuba. Expect a line for photos; a quick picture together and you are done. Head back to the room for the hottest part of the afternoon.
Sunset at Mallory Square
In the late afternoon, walk north up Whitehead to Mallory Square on the harbor. The Sunset Celebration runs nightly, weather permitting, starting about two hours before sunset: jugglers, musicians, food carts and a crowd facing the water as the sun drops behind the islands to the west.
It is free. Arrive about 45 minutes before sunset to find a spot on the edge of the pier, then walk Duval Street afterward for dinner. If the crowd is too much, walk a few minutes along the harbor boardwalk for a quieter view of the same sky.
The whole day is on foot: base → Hemingway Home, about 10–15 minutes; Hemingway Home → lighthouse, across the street; lighthouse → Bahama Village, about 5 minutes; Bahama Village → Southernmost Point, about 10 minutes; Southernmost Point → Mallory Square, about 25 minutes up Whitehead Street.
Where to stay
- The Marquesa Hotel — a cluster of restored 1880s houses with two pools, in the heart of Old Town a block off Duval Street.
- The Gardens Hotel — or a quiet Old Town hotel set in a large tropical garden, a few blocks from Duval Street.
Dinner: on or near Duval Street after the sunset; book ahead in peak season, when the walk-in waits get long.
Tomorrow: an early start, check-in at the ferry terminal at 7 a.m., about 10–15 minutes on foot from Old Town.
Bad-weather plan
Rain on Day 1? Swap the Southernmost Point for the Mel Fisher Maritime Museum on Greene Street, with gold and silver from the 1622 Atocha wreck, and see the Audubon House gardens once it clears; showers are often short.
Stay: Old Town base · Anchor: Hemingway’s house · gate tickets only; about $19
Good to know: The Hemingway Home sells tickets only at the gate and does not take reservations; the lighthouse closes to new visitors at 4:30 p.m.
