Seven days in the Florida Keys: a hundred and thirteen miles of road with sea on both sides
Miami to Islamorada to Key West by car, six nights: Art Deco and Cuban coffee, a stop halfway down the chain, and three nights at the end of the road.
- Length
- 7 days, 6 nights
- Where you stay
- Miami, Islamorada, Key West
- Places
- 19 across 7 days

The Overseas Highway runs a hundred and thirteen miles from the Florida mainland to Key West across forty-two bridges, and for long stretches there is water on both sides of the car and nothing else in view. It was built on the piers of a railway that a hurricane destroyed in 1935, which is the sort of fact that improves the drive considerably.
The islands themselves are not the Caribbean, whatever the marketing says. They are low, scrubby, mangrove-fringed coral rock with a single road down the middle, and the point of them is what is in the water: the only living coral barrier reef in the continental United States, running the whole length of the chain a few miles offshore.
Seven days does it properly. Two nights in Miami first, because it would be strange to fly into one of the most interesting cities in the country and drive straight past it; one night halfway down; and three at the end of the road, in a town that declared independence from the United States in 1982 as a publicity stunt and has never entirely dropped the joke.
Highlights
- Seven miles of bridge with the old railway spans running alongside it
- Cuban coffee handed through a window on Calle Ocho, drunk standing on the pavement
- Snorkelling a reef that starts a few miles offshore and runs the length of the chain
- Six-toed cats on the wall of a writer's house, descended from the ones he kept
- The sunset crowd at Mallory Square, which has been an organised event since the 1960s
Where to stay

Miami, two nights
Two cities that people confuse: Miami Beach, the barrier island with the Art Deco and the sand, and Miami proper on the mainland, which is much larger and where the working language of whole neighbourhoods is Spanish.
Two nights gets you an afternoon on Ocean Drive and a morning on Calle Ocho, which is the honest minimum. Stay in South Beach for the walking and collect the car on the morning you leave.
Islamorada, one night
About 102 km from Miami.
Not one island but a string of them in the upper middle of the chain, calling itself the sport fishing capital of the world with some justification: the flats on the bay side and the reef on the ocean side are within a few minutes of each other.
One night, chosen as a stop rather than a destination. It breaks the drive, it has the state parks and the wrecks, and it is where you get onto the water without the crowds of Key Largo.

Key West, three nights
About 125 km from Islamorada.
Four miles by two, and a genuinely odd place: a nineteenth century wrecking and cigar town of tin-roofed clapboard houses that has been a navy base, a hippy refuge, a gay resort and a cruise stop, and is all of those at once.
Three nights is right. One for the town, one for the water, and one for doing nothing, which is what the island is actually for.
Day by day
Day 1 in Miami
South Beach: the Deco district and the sand
The first afternoon does not leave the island and barely leaves ten blocks.
The Art Deco Historic District is about eight hundred buildings from the 1920s to the 1940s in a square mile, the largest concentration of the style anywhere, and it survives because a preservation campaign in the 1970s stopped the lot being knocked down for towers. Walk Ocean Drive, then one block inland on Collins and Washington, where the buildings are less painted and more interesting.
Española Way is two minutes west, a short block built in 1925 as a mock Mediterranean village, pedestrianised and lined with tables under awnings.
Then the beach, which is genuinely enormous: a hundred metres of sand from the dune line to the water, with lifeguard huts in colours that are themselves photographed constantly.
Eat late, because everybody here does, and preferably not on Ocean Drive, where the service charges catch people out.
- 15:00
Art Deco District
VisitWalk it rather than reading about it. The visitor centre on Ocean Drive runs a good ninety minute guided walk each morning. Come back after dark when the neon is on.
- 16:45
Espanola Way
ArchitectureOne short block of 1925 pastiche, closed to cars, with tables down the middle. Ten minutes to look and longer if you sit down.
- 17:45
Lummus Park
LeisureThe strip of park behind Ocean Drive, with the beach beyond it and a promenade running the length of South Beach. Free and shaded.

- 19:00
The beach
VisitWide, clean and public, with chairs and umbrellas for hire from the hotels. The water is warm all year. Swim before six, when the lifeguards go off.
With more time: The Versace mansion on Ocean Drive at 11th Street was built in 1930, remodelled by the designer in 1993 and is where he was shot on the front steps in 1997. It is a hotel now and the steps are still there.
Day 2 in Miami
Calle Ocho, a villa on the bay, and two museums
Cross to the mainland for the day. This is the half of Miami most visitors skip and it is the more interesting half.
Calle Ocho is Southwest 8th Street and the spine of Cuban Miami. Start with a coffee at a walk-up window, then walk: an Art Deco cinema from 1926 that showed subtitled films to newly arrived Cubans learning English, cigar rollers working in shop windows, and a park where men in guayaberas play dominoes competitively and have done for decades.
In the afternoon, fifteen minutes south to Vizcaya, where James Deering built himself a Renaissance villa on Biscayne Bay between 1914 and 1922, filled it with four centuries of European furniture, laid out formal gardens behind it and moored a carved stone barge in the water in front as a breakwater. About a thousand people worked on it in a town of ten thousand.
Back on the beach in the evening, the Wolfsonian is the best museum in Miami and almost nobody goes: a 1920s storage warehouse where wealthy winter residents left their furniture between seasons, now holding the design and propaganda of the industrial age. It opens late on Fridays.
Ten minutes north of it, the Holocaust Memorial is not a museum and takes twenty minutes and is the thing people remember from this city.
- 10:00
Vizcaya Museum and Gardens
HistoricBuy the ticket online. Do the house first and the gardens after, which is the reverse of what everybody else does. Closed Tuesdays. Two and a half hours.

- 12:45
Lunch on Calle Ocho
EatRopa vieja, a cortadito from the window on the side of the building, and a pastelito. The domino park is a few doors along; watch from the railing rather than through the gate.
- 15:00
Wolfsonian
CultureClosed Wednesdays, open late on Fridays, and free on Friday evenings. Start on the top floor and work down. Two hours.

- 17:15
The Holocaust Memorial
VisitFree, open every day, about twenty-five minutes. Enter through the colonnade rather than from the car park; the approach is designed as a sequence and it matters.
With more time: Collect the hire car this evening rather than in the morning. The causeways back up badly at rush hour and the drive south starts better before nine.
Day 3 in Islamorada
Down the Overseas Highway to Islamorada
A hundred kilometres and about two hours without stopping, which nobody manages. The road leaves the mainland south of Homestead, crosses eighteen miles of mangrove and sawgrass with nothing on either side, and arrives at Key Largo, where the mile markers start counting down.
Stop at Key Largo for the underwater park, which was the first of its kind in the country and protects a stretch of the reef. Glass-bottom boats, snorkelling trips and dives all leave from the same marina, and the two and a half hour snorkel trip is the easiest introduction to the reef on the whole chain.
Islamorada is another thirty minutes south. It is a string of islands rather than a town, with fishing lodges, art galleries in old conch houses and a fair number of pelicans standing on things.
The memorial on the ocean side commemorates the Labor Day hurricane of 1935, which killed several hundred people, most of them First World War veterans working on the highway, and destroyed the railway that ran down these islands. It is a stone plaza with a crypt under it and it takes fifteen minutes.
Then a quarry full of fossil coral, cut for building stone in the 1900s, where the saw marks reveal the cross sections of a reef that grew here 125,000 years ago. Eat on the water and turn in early.
- 14:00
The Florida Keys Memorial
VisitA stone plaza and crypt on the ocean side at mile marker 82, commemorating the 1935 hurricane and the men who died building this road. Free, and fifteen minutes.
- 15:00
Windley Key Fossil Reef Geological State Park
LeisureA former quarry where the cut faces show a fossil reef in cross section, with a short trail through the workings. Small entry fee, an hour, and take insect repellent.
- 16:45
Long Key State Park
LeisureThe oldest state park in the Keys, with a beach on the ocean side, a boardwalk through the mangroves and a canoe trail. A good place to swim before the sun goes.
- 19:00
Dinner on the bay side
EatBay side for sunset, ocean side for the fishing boats. Order whatever came in that afternoon, grilled, and a slice of key lime pie, which is yellow rather than green wherever it is made properly.
With more time: Two of the islands off Islamorada are state parks reachable only by boat: one holds a hardwood hammock that has never been cleared, the other the ruins of a town wiped out in a raid in 1840. The ferries run on limited days and both are worth checking.
Day 4 in Key West
The Seven Mile Bridge, and the end of the road
A hundred and twenty-five kilometres to Key West, about two hours without stops and half a day with them. This is the best of the driving.
The Seven Mile Bridge is halfway down and is the one everybody photographs, with the old railway bridge running alongside it, disused and broken in the middle, carrying nothing. A restored section at the northern end is open to walk and cycle and goes out to a small island with a house on it.
Bahia Honda, just past the bridge, has the best beach in the Keys by common consent: real sand rather than rubble, shallow water, and the shattered end of the old railway bridge standing over it.
Key West appears at the end of a causeway in the early afternoon. Check in, leave the car where it is for the next three days, and walk.
Then Mallory Square for sunset, which is an organised event with jugglers, a cat trainer, buskers and a crowd, and has been every evening since the 1960s. It is exactly as touristy as it sounds and everybody goes anyway.
- 16:30
Southernmost Point
HistoricA concrete buoy on the corner of Whitehead and South, claiming ninety miles to Cuba, which is roughly right. There is always a queue and it moves. Go early or late.

- 17:30
Key West Lighthouse
ArchitectureEighty-eight steps to the lantern, and the only high view on a very flat island. The keeper's house at the base is included. Best in the last two hours of light.

- 18:45
Sunset at Mallory Square
NoteBuskers, a crowd and the sun going down behind the Gulf. Free. Arrive about an hour before, which is when the performers start rather than when the sun does.
With more time: The bar crawl on Duval Street is the thing Key West is famous for and it is a young, loud, largely cruise-ship affair. The bars one street back are where the people who live here drink.
Day 5 in Key West
Hemingway's cats, the Little White House and a fort on the beach
The town day, and everything is within a mile.
The Hemingway house is a Spanish colonial villa with a wraparound veranda where he lived for about a decade in the 1930s and wrote To Have and Have Not and much of the Spanish Civil War material. He kept cats; around fifty of their descendants still live on the grounds and roughly half carry the extra toe. The guided tour is short and included, and the writing studio over the old carriage house is the reason to take it.
Ten minutes away is the Little White House, a naval officers' quarters that Harry Truman used as a working retreat for 175 days across eleven visits, left almost exactly as it was, with the poker table he had built into the sun porch.
In the afternoon, walk to the fort at the western tip. It was begun in 1845, held for the Union through the Civil War in a Confederate state, and the beach in front of it is the best swimming on the island: deep water close in, actual sand, and shade under the Australian pines.
Eat conch fritters somewhere, and take the sunset from the fort rather than the square if you would rather have it quietly.
- 10:00
Ernest Hemingway House
CultureGuided tours run continuously and are included; take one. About an hour. The cats are everywhere, they are used to people, and the ones with six toes are labelled.

- 12:00
Harry S. Truman Little White House
HistoricGuided tours only, roughly every half hour, about fifty minutes. The grounds and the botanical garden around it are free to walk in even without a ticket.
.jpg%3Fwidth%3D500)
- 13:30
Lunch off Duval
EatConch fritters, a grouper sandwich and key lime pie. Anywhere a street or two back from Duval will do it better and cheaper than anywhere on it.
- 15:00
Fort Zachary Taylor
HistoricA state park at the western tip with a brick fort from the 1840s and the best beach on the island. Small entry fee. Snorkelling straight off the sand, and shade, which is scarce here.

With more time: The city cemetery is nineteen acres in the middle of town with the tombs above ground because the rock is too hard to dig, and a headstone reading I told you I was sick. Half an hour and almost nobody there.
Day 6 in Key West
Out to the reef, or out to the Dry Tortugas
The water day, and there are two versions of it.
The short one: a snorkelling or diving boat out to the reef, which is six miles offshore here, for a half day. Sailing catamarans do the same trip with lunch and rum on the way back, which is a very Key West way to spend an afternoon.
The long one, and the better one if you can get a seat: the Dry Tortugas, seventy miles west, a cluster of sand islands in open ocean holding Fort Jefferson, an unfinished nineteenth century brick fortress of sixteen million bricks that was used as a prison and is now reachable only by ferry or seaplane. The ferry runs about two and a quarter hours each way, includes lunch and snorkelling gear, sells out weeks ahead, and leaves you four and a half hours on the island. It is the best day trip in Florida.
Whichever you choose, come back in time for the eco-discovery centre by the naval basin, which is free, small and explains the reef, the mangroves and the Everglades system that feeds them better than anything else in the Keys.
Last dinner, and one drink somewhere with a band in it.
- 09:00
Shipwreck Museum
VisitA sailing catamaran doing daily snorkel trips and an evening sunset sail from the marina. Book the morning trip; the water is calmer and the light on the reef is better.
- 15:00
Florida Keys Eco-Discovery Center
CultureFree, air conditioned and much better than it looks from outside. A reconstructed underwater laboratory, a living reef tank and a good film. An hour.
.jpg%3Fwidth%3D500)
- 16:45
Key West Art and Historical Society Museum
VisitIn the old brick fort on the eastern side of the island, covering the wreckers who made this town rich by salvaging ships off the reef. Ninety minutes.
With more time: The Dry Tortugas ferry leaves at eight and books out weeks ahead in season. If you want it, arrange it before you leave home and rearrange this day around it; there is no way to do it on a whim.
Day 7 in Key West
One last swim, and the road or the runway
Key West has a small airport with connections through Miami, Fort Lauderdale and Tampa, which is the easy exit and usually the expensive one. Driving back to Miami is four hours and worth allowing five.
Before either, take the morning slowly. The wildlife rescue centre near the beach takes in injured birds and has released a couple of thousand of them since 1993, and it costs nothing to walk round.
Then a last swim, a last coffee, and the mile markers counting back up.
- 09:30
McCoy Indigenous Park
VisitA small volunteer-run rescue centre for birds and turtles, free to visit, near the eastern beaches. Half an hour, and the volunteers will tell you about every resident.
- 11:00
Breakfast before the road
EatCuban coffee and a ham croquette from a walk-up window, which is how this island starts the day and how the drive back should start too.
With more time: If you are driving back, stop at Bahia Honda again on the way up. It is the best beach on the chain and it is emptiest before ten in the morning.
Before you go
The car and the road
Hire in Miami and drop in Key West, or drive back up, which takes four hours and is not unpleasant. There is a bus down the Keys and a shuttle from Miami airport, and neither of them will let you stop.
The whole route is measured in mile markers, counting down from 106 at Key Largo to zero in Key West, and every address, restaurant and dive shop gives its location that way. The speed limits are low and enforced, the road is single carriageway for most of its length, and the traffic backs up behind anything slow with no way past.
The water
The reef is the reason to come and it is three to six miles offshore, so you need a boat. Snorkelling and diving trips run from every key and cost about the same; the best known are the ones out of Key Largo to the underwater park and the Christ of the Abyss statue.
Use only reef-safe sunscreen, do not stand on or touch the coral, and be honest with the crew about your swimming. The current on the reef is stronger than it looks from the boat.
Hurricanes and the season
December to April is the high season: dry, warm, expensive and full. May and November are the sweet spots either side of it.
June to November is hurricane season, peaking in September, and the Keys are the most exposed inhabited place in the country. There is one road out and it is a single carriageway, so evacuation orders come early. Watch the forecast before you travel, and think hard about a non-refundable September booking.
What it costs
More than you expect. Everything on the islands is trucked in over that one road, hotel rooms are limited by the geography and priced accordingly, and Key West in season is comparable with a European capital.
The ways round it are the state parks, which are cheap and are the best beaches on the chain, and eating where the boat crews eat rather than on the waterfront.
The drive is the trip. A single road on the spans of a railway that a storm took away, with the ocean on one side and the Gulf on the other and no way to hurry.
Watch the mile markers count down, and stop at the ones that look like nothing.
Go deeper on one city
Each of these covers a single stop on this route in its own right.
Make it your trip
Every stop, day and place here lands in your account as an editable trip. Move the days around, swap a city, add your own bookings and costs, and share it with whoever is coming.
Common questions
- Is seven days enough?
- It is comfortable, and two of those days are Miami. If you only want the islands, five works: one night in the upper Keys and three or four in Key West. Adding days is best spent in Key West or on the water rather than on more stops down the chain.
- Do I need a car?
- For the drive, yes. In Key West, no: the island is four miles by two, everybody cycles, and hotel parking is expensive. Park the car when you arrive and do not touch it until you leave.
- Where are the good beaches?
- There are fewer than people expect, because the reef offshore stops the sand forming. Bahia Honda near the Seven Mile Bridge is the best on the chain; Fort Zachary Taylor is the best in Key West. Most of the rest are made or are rubble.
- Is the Dry Tortugas trip worth it?
- Yes, and it is the single best day on this route. Seventy miles out into open water, a vast unfinished brick fort on a sand island, and snorkelling straight off the beach onto coral. The ferry sells out weeks ahead and there is a seaplane if it has.
- When should I avoid?
- September, which is the peak of hurricane season, and the last week of October, when the Fantasy Fest costume carnival fills Key West completely. Christmas through March is the most expensive and the most pleasant.
- Is it family friendly?
- The drive and the water are, entirely. Duval Street after dark in Key West is not, and the town has a long tradition of not pretending otherwise. Stay a few streets back and the island is a very easy place with children.