Key West
THE AMERICAS · ISLAND · CARIBBEAN EDGE
The end of the road — 200km of bridges out into the Gulf to an island that is closer to Havana than to Miami. Key West is small, low, tin-roofed and deeply eccentric, with Hemingway's cats, a nightly sunset ceremony, and a bar culture that starts early. Snorkel the only living coral barrier reef in the continental US while you're here.
The plan
Drive the Overseas Highway
The 200km approach over 42 bridges, including Seven Mile Bridge. Stop at Bahia Honda for the best beach in the Keys.
Snorkel or dive the reef
Boats run out to Sand Key and the Vandenberg wreck. The only living barrier reef in the continental US.
Mallory Square sunset
Jugglers, a bagpiper and the whole town applauding the sun. Absurd and obligatory.
Hemingway Home
Where he wrote for a decade, with 60-odd six-toed cats still in residence. The tour guides are excellent.
Duval Street, one end to the other
Sloppy Joe's, Captain Tony's and the Green Parrot — the last of which is where locals actually drink.
Book before you fly
Dry Tortugas
The Yankee Freedom ferry and the seaplanes are both capped and book weeks ahead.
Reef snorkel & dive trips
Morning boats are calmer; book the day before.
Fantasy Fest & New Year
Late October and 31 December — the two most expensive weeks of the year.
Getting there
Fly Key West (EYW)
On the island, with direct flights from Miami, Atlanta, Charlotte and a few northern cities in winter. Fares are high.
Fly Miami (MIA) and drive
Three and a half hours down the Overseas Highway, and the drive is genuinely part of the trip.
Take the Key West Express
A high-speed ferry from Fort Myers in about four hours — a good option from Florida's west coast.
When to go
Best time to go
December to April — dry, 25°C, and the reason it's called season. Book well ahead.
Cheapest months
September and October, the deepest hurricane months, when rooms fall by half.
Priciest & busiest
Fantasy Fest in late October and the New Year week, when rates are at their absolute peak.
If you've got one day
Morning
Drive the Overseas Highway
Late morning
Snorkel or dive the reef
Lunch
Garbo's Grill
Afternoon
Hemingway Home
Sunset
Mallory Square sunset
Evening
Dinner at Latitudes, then Duval Street, one end to the other
If you've got a week
Day 1
Arrive, settle in around The Marker, and take it slowly — Garbo's Grill for dinner.
Day 2
Drive the Overseas Highway.
Day 3
Snorkel or dive the reef. Dinner at Blue Heaven.
Day 4
Day trip — Dry Tortugas.
Day 5
Mallory Square sunset. Latitudes at some point.
Day 6
Hemingway Home.
Day 7
Duval Street, one end to the other. Finish with El Siboney.
Staying longer?
Nearby & day trips
Dry Tortugas
70 miles west by ferry or seaplane to a brick fort and the clearest water in the US.
Bahia Honda State Park
Forty minutes back up the Keys to the best beach in the chain.
Three and a half hours north at the top of the highway.
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