Key West is closer to Havana than to Miami, four miles long by two wide, and has spent most of its history being a slightly lawless island that happens to belong to the United States.
It briefly declared independence in 1982 as the Conch Republic, surrendered after one minute, and applied for foreign aid. That tells you most of what you need to know about the place.
Two days is right. Here’s how to spend them.
Stay the Night, Whatever You Do
This is the single most important decision about Key West and it’s not really about hotels.
The island gets cruise ships and day-trippers driving down from Miami. From about ten in the morning to five in the afternoon, Duval Street is a crush.
Then the ships leave, the day people drive back, and the island becomes an entirely different, much better place. Locals come out. Restaurants have tables. The streets are quiet.
If you only see Key West between 10am and 5pm you’ll wonder what the fuss is about.
Day 1, Afternoon: Walk the Old Town
Get off Duval within about ten minutes and into the residential streets either side.
What’s there: wooden conch houses from the 1800s, built by ship carpenters, with wraparound verandas, gingerbread trim and tin roofs. Frangipani and bougainvillea over every fence.
Chickens. Hundreds of them, descended from birds kept for cockfighting, legally protected and entirely unbothered by traffic.
Six-toed cats too, around the Hemingway house, descended from a ship’s cat given to him in the 1930s. Roughly sixty of them live on the grounds.
▶ Watch This Before You Go
Day 1, Evening: Mallory Square and After
The sunset celebration on the waterfront has been running nightly since the 1960s. Jugglers, buskers, a man with trained house cats, and a few hundred people watching the sun go into the Gulf.
Get there an hour early for a spot at the rail. It’s free and it’s genuinely charming rather than cynical.
Then eat. Key West food is conch fritters, stone crab in season, yellowtail snapper and pink shrimp. And key lime pie, which should be pale yellow, never green.
Duval Street at night is loud and drink-focused, and the bars at the north end are the historic ones. Two blocks east on Petronia Street in Bahama Village is calmer and better.
Day 2, Morning: Hemingway’s House
Hemingway lived here from 1931 to 1939 and wrote several of his best-known books in a studio above the carriage house.
The house is Spanish colonial, the gardens are lovely, and the tours run every half hour and are led by guides who are enthusiastic and mildly unreliable about facts.
The swimming pool cost 20,000 dollars in 1938, which was an absurd sum, and there’s a penny embedded in the concrete beside it from an argument about money.
Cash or card, small entry fee, an hour. Go at opening before the cruise crowd.
Day 2, Late Morning: The Lighthouse and the Museums
The lighthouse across the road from Hemingway’s house is 88 steps up and gives you the best view on the island, which is not saying much on somewhere this flat, but it’s a good one.
The Mel Fisher Maritime Museum has treasure from a Spanish galleon that sank in 1622 and was found in 1985. Actual gold bars you can lift.
The Custom House museum and the Truman Little White House, where Truman spent 175 days of his presidency, are both worth an hour if the weather turns.
Day 2, Afternoon: Get on the Water
Key West is an island and most visitors never leave the pavement, which is a mistake.
The reef is a few miles offshore, the only living coral barrier reef in the continental US, and snorkel trips run several times a day.
Sunset sails are the classic evening option, usually with drinks included, and they’re a much better way to watch the sunset than standing in Mallory Square if you’ve already done that.
Kayaking through the mangroves in the backcountry is the quiet option, with birds and rays and no engine noise.
The Southernmost Point, Honestly
A painted concrete buoy on a street corner marking the southernmost point in the continental United States, 90 miles from Cuba.
Except it isn’t quite. The actual southernmost point is on naval land nearby and inaccessible, so this is close enough for the photo.
The queue is regularly 30 to 45 minutes in season for a picture of a marker. Go at 7am and there’ll be nobody, or accept that it’s a queue and skip it.
Not a scam, just a very ordinary thing that people spend a surprising amount of their holiday waiting for :/
If You Have a Third Day
Dry Tortugas National Park. Seventy miles west by ferry or seaplane, a colossal 19th century brick fort on a tiny island, and the best snorkelling in Florida.
It’s a full day and the ferry books out weeks ahead. It’s also the least visited national park in the continental US and it’s extraordinary.
Alternatively, drive back up the Keys slowly and stop at Bahia Honda and Islamorada, which most people blow past on the way down.
Practical Things
Don’t drive in Key West. The old town is small, parking is expensive and scarce, and everything is within twenty minutes on foot. Hire a bicycle or a scooter instead.
Everything is more expensive than the mainland, because everything arrives by lorry down a 113 mile road.
December to April is high season with the best weather and the highest prices. Summer is hot, humid and much cheaper. Hurricane season runs June to November, peaking in September.
Sun protection matters here more than people expect. You’re at 24 degrees north with a lot of reflected light off the water.
Common Questions
Is 2 days enough for Key West? Yes for the island itself. Add a third if you want Dry Tortugas or a proper day on the reef.
Should I stay overnight or day trip? Stay. The island changes completely once the cruise ships and day-trippers leave in the late afternoon.
Do I need a car in Key West? No, and it’s a liability. Walk, cycle or take a scooter.
Is the Southernmost Point worth queuing for? Not for 40 minutes. Go early or walk on.
When is the best time to visit? March and April, for warm dry weather after the peak winter prices have eased slightly.
