Closer to Cuba than Orlando, the laid-back Florida Keys are a world away from mainland USA. Dress code is casual, cocktails are potent and everyone slows down to island time. It used to be that the only way to navigate the 1,700 tiny islands that string out from the southernmost point of the USA was by boat (“key” is an English corruption of the word “cayo”, which means island). Today, the scenic Overseas Highway cuts all the way from Miami to historic Key West, navigating 42 bridges along the way.
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Where to go in the Florida Keys
Like a lot of the USA beyond the big cities, in the Keys, communities are spread out along the highway. Here though, the road is hugged by the sea on both sides, palm trees and vibrant bougainvillea line the sidewalk, and retro signs for diners and motels jostle for space with those for Cuban coffee and shrimp shacks. We’ve listed the major destinations, but the Florida Keys tourism site is a great resource for more information.
Key Largo
The northern gateway to the Keys is the perfect place to spend a couple of nights if you fly in via Miami Airport. With two state parks and a marine sanctuary, you can hike nature trails through the subtropical wilderness and dive or snorkel some amazing coral reefs. For culture buffs, The African Queen, from the 1951 movie of the same name starring Humphrey Bogart and Katharine Hepburn, cruises the canals from the Marina Del Mar.
A mangrove in Key Largo by Jo Crebbin/Shutterstock
Islamorada
Made up of a group of six separate islands, Islamorada is self-styled as the sport fishing capital of the world. Charter boats ply the Atlantic Ocean and the “backcountry” waters of the Gulf of Mexico. The world-class marinas tend to be at the centre of life here, and you can head to Robbie’s Marina to book a boat or hand-feed massive tarpon. Islamorada is also known for its stylish resorts including Cheeca Lodge & Spa.
Key West
The atmospheric old town in Key West is at the end of the road, the southernmost tip of the Keys. Key West grew rich from cigar-making (brought here by the Cubans) and from the wrecking business, a lucrative industry when ships laden with goods from the New World would wreck on the coral reef and be plundered. Today, the city’s white-washed mansions and pastel cottages have been restored to their former glory, but Key West retains a “come as you are” feel.
A “One Human Family” motto has been adopted by the city’s sizeable LGBTQ+ community and expensive seafood restaurants happily coexist with dive bars. This is, after all, the place that Ernest Hemingway called home. Charming and atmospheric, Key West is overrun with tourists but the locals don’t seem to mind.
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The best Florida Keys hotels
In Key Largo, stay at the waterfront Key Largo Bay Marriott Beach Resort overlooking the Gulf of Mexico. The best rooms have balconies with pool and beach views, plus there’s a well-equipped dive shop and marina.
Further south in Islamorada, Cheeca Lodge and Spa is a relaxed and luxurious resort. It’s got a reputation for being where the celebs hang out (a fair few Presidents have stayed here too) and service is spot on. After Hurricane Irma slammed through in 2017, the wooden fishing pier had to be rebuilt and it was a chance to completely revamp the hotel.
Nestled midway down the Keys is Hawks Cay Resort in Duck Key. The sprawling 60-acre complex reopened in August 2018 after renovations to fix damages caused by Hurricane Irma the year before. The atmosphere here is family-friendly with the option of staying in the chilled-out, luxe main hotel or self-catering villas. But there are plenty of places for grown-ups to retreat to – hang out in the spa, by the adults-only pool or book dinner for two at one of the resort’s excellent restaurants.
A relatively new addition to Key West, Oceans Edge Key West Hotel and Marina is on fast-developing Stock Island, four miles east of the old town. There’s a complimentary hourly shuttle, but with six ocean-front pools and an open-air waterside restaurant and bar, you probably won't want to leave. The charming Key West architecture is the inspiration for the buildings here, and suites and rooms are vast.
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What to eat in the Keys
Fresh, zingy and sweet, key lime pie is a must. Everyday. Debate rages as to whether it should be topped by meringue or whipped cream, so be sure to try it with both.
The Keys offer a bewildering array of seafood and depending on the season, you’ll find mahi-mahi (also called dolphin by some locals – don't worry, it's not the mammal), hog snapper, yellowtail, tarpon and grouper on the menu. Every shack and restaurant offers conch (pronounced konk) and although the sea snail is imported from the Bahamas these days, it’s hugely popular (most commonly served as fritters). Other delicious shellfish includes jumbo stone crab claws, pink shrimp, lobster, mussels and scallops.
During Prohibition, bars down here stayed open for business with booze imported from Cuba and the Keys still have a reputation for hard drinking. Beer lovers and rum drinkers are very well catered for, with award-winning breweries and small batch distilleries to visit.
The ultimate five-day Florida Keys itinerary
Day 1
Check-in to: Key Largo Bay Marriott Beach Resort. Opt for a sea-view room with a balcony for the best sunsets.
Go snorkelling at: John Pennekamp Coral Reef Resort. Cruise out through the mangrove swamps to an underwater coral reef with nothing beyond it until the Bahamas.
Lunch at: Mrs Mac’s Kitchen I or Mrs Mac’s Kitchen II. These two quirky diners – the original dates to 1976 – are packed with character and satisfied regulars. The key lime pie is to die for.
Take it easy: at the pool back at the resort, or on its small artificial beach.
Dine at: Sundowners. Sunsets and fresh seafood since 1985. This is the kind of place where you can kick back and watch a game on the screens in the bar, or head outside to the decking to watch the sun go down and chat with friends until the small hours. Order the chargrilled mahi-mahi with a smothering of caper sauce and a side of irresistibly garlicky green beans. Dedicated carnivores will love the BBQ baby back ribs – people come from miles around for them.
Top tip: leave space for something sweet. The mammoth key lime pie is a must-try.
Day 2
Take a drive along: the Overseas Highway to cross the epic seven-mile bridge. At mile marker 37, stop at Bahia Honda State Park to paddle in the sea and walk up to the original railroad bridge. The beach is the perfect place for a picnic breakfast or lunch.
Check-in to: Oceans Edge Resort and Marina.
Bike tour in: Key West. To get your bearings, take a bike tour around the historic district with Key Lime Bike Tours. Alternatively, for a more laid-back way to explore the city, jump on a Conch Tour Train. The open-air 'train' on wheels makes its way through the main old town thoroughfares and pretty residential streets, while a guide tells the story of Key West's history and points out notable buildings. There are a couple of hop-on, hop-off stops along the way if you want to break up the 75-minute ride.
Watch the sunset: at Mallory Square. Sunsets are a must-see in this area, and Key West has created a nightly sunset celebration in Mallory Square (they take it so seriously that the vast cruise ships moored here must leave before sunset or they will be fined $15,000 for spoiling the view).
Dine at: Turtle Kraals. This chilled-out local spot is a great place to kick back and fill up. The ceviche menu of different fresh raw fish cured in citrus juices is incredible. The Peruvian Classico is a winner: yellowtail snapper, sweet potato and key lime leche de tigre. Or, try a ceviche flight to sample several styles.
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Day 3
Take a stroll: around Historic Key West. This area of town is wonderful to explore on foot and the house and shady grounds at the Ernest Hemingway Home and Museum are unmissable (look out for the six-toed cats that are descended from a white polydactyl cat owned by Hemingway).
Lunch at: Cuban Coffee Queen. The line out of the door at this Key West institution says it all. Grab a sandwich, coffee or smoothie to go.
Spend the afternoon on a boat: and explore a different side to Key West. On an Island Adventure Eco Tour with Fury Water Adventures, you'll be whisked out to sea to snorkel and kayak in crystal waters, around remote sandbars and close to protected mangroves. After you've worked up an appetite, the crew lay on a feast of fried chicken, sandwiches and cookies. Catch the sunset trip to end the day watching Key West bathed in orange with a glass of champagne in hand.
Get your thrills: with night kayaking. A few places offer night kayaking, but at Ibis Bay Beach Resort you can do it in a glass-bottomed boat, with LED lights to illuminate the ocean floor. You’re likely to see lobsters, jellyfish, sea cucumbers and tropical fish. If you get lucky you might spot a turtle or manta ray.
Dine at: The Stoned Crab. Working with local sea captains, The Stoned Crab is all about responsible and delicious seafood. Eco-cocktails round things off nicely.
Day 4
Fly to: the Dry Tortugas. This is a highlight of any trip to the Keys, and taking a seaplane for a day trip to the remote islands is a once-in-a-lifetime experience. Everyone gets a window seat for a bird's-eye view of turtles, sharks and shipwrecks below, and the island itself boasts white-sand beaches, sensational snorkelling and the majestic Fort Jefferson. Pack a picnic.
Day 5
Take in: Key West's sights. Stop in at the Butterfly and Nature Conservatory or the Mel Fisher Maritime Museum.
Lunch at: Keys Fisheries. Once you’ve checked out, drive to Marathon for lunch. Keys Fisheries might be casual (order from the hatch) but it serves the best lobster reuben for miles around.
Check-in to: Hawks Cay Resort. Stay here for a night (or three) of relaxation. The most you’ll want to do is a few laps of the pool or book a treatment at the spa.
Explore: Islamorada. If you can tear yourself away from a sunbed, drive to Islamorada, a 30-minute car journey away. Chef Michael’s, a sophisticated seafood restaurant with an ever-changing menu and knowledgeable waiting staff, is a special spot for a Friday night meal. Make time to browse Morada Way, the nearby arts and cultural district.
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Florida Keys map
Navigate the Florida Keys with our handy map: