Your guide to the sun-soaked Florida Keys
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December 14, 2022 | View OnlineSign Up

The Florida Keys may be classed as part of the United States, but as you count down the mile markers on Seven Mile Bridge, you’ll have the pleasant inclination you’ve headed elsewhere – somewhere freer and more relaxed, where time rolls a little slower, and you can practically feel the lure of the not-too-distant Caribbean.

While the stretch of idyllic islands may have a reputation as a snowbirds’ paradise, its attractions are diverse and pull a much wider crowd than assumed. From big game fishing to underappreciated historical sites, the Keys are far more than a sweet escape.

Welcome to the Florida Keys.


They are way bigger than you thought

If you’ve never been to the Keys, you might think the islands are limited to a few big-name spots like Islamorada or Key West. In reality, the Florida Keys span 800 individual islands, stretched out over 180 miles.

Of course, you need a lot of bridges to access these – 42 of them, to be precise. The longest of these is Seven Mile Bridge, which connects the Keys to the mainland, while the shortest, the Harris Gap Bridge, is only 37 feet long.

All of the highways are part of a 113-mile section of US Route 1, which runs from the Canadian border all the way down – 2,370 miles while we’re listing stats.


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Rent a car

While you can fly into Key West, the US’ southernmost city, you’d be missing out heavily on one of the country’s most stunning drives.

Instead, fly into Miami or Fort Lauderdale, pick up a rental and get truckin’ down along the Overseas Highway. Not only will you enjoy the vastly diverse scenery and the unique experience of driving across open water, but you’ll have more freedom to enjoy the rest of the islands while you’re there.

There are surprisingly few beaches

While you might associate the Florida Keys closely with the Caribbean, you might be surprised to find a surprising lack of beaches. Don’t get it wrong, there are some beautiful little sandy spots, but don’t expect to see many expansive stretches of sand as you’d do in other parts of Florida.

The lack of sandy beaches owes to the presence of the nearby coral reef, which helps prevent erosion and, in turn, sand. So if you’re a little disappointed, just remember the world-class scuba and snorkeling opportunities you’re afforded instead.

Plan in advance and grab some vouchers

It shouldn’t be news to you, but the Keys can be extremely crowded – especially in winter. Thousands of snowbirds flock South in the winter months, along with swathes of sports fishers and Floridian city-slickers on weekend getaways, so it can get a little chaotic for the unprepared.

Planning your trip well in advance will save you a lot of stress and, more importantly, a lot of money. Rental car prices will be lower when booked well in advance, and availability on excursions you want to book will be more varied than waiting until your arrival.

Pro-tip - grab a Vacation Discount Booklet from The Key West Attractions Association. While you might flinch at its $54.99 price point, it features a number of BOGO offers, discounts, and multi-pass offers that can save you well over that number. The association itself claims there are over $850 of savings. 


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Get to grips with Key West

Easily the most recognizable tourist spot in the Keys is the famous buoy that marks the Southernmost point in the Continental United States. Unless you can get there early, there’s a fair chance you’ll be waiting in line for a snap with the buoy. Thankfully, if you don’t feel like waiting, you’ll be happy to realize you’re in Key West, a surprisingly edgy little city and the Keys’ largest island.

It’s here you’ll find the most things to do, and it’s a good place to base yourself for a few days on your trip. It’s packed with wonderful restaurants, intriguing museums, and even unexpected historical sites.

For those with an eye on the arts, you’ll find several excellent visits in Key West. Key West Museum of Art & History at the Custom House is the standout attraction. Housed in the old customs building, the museum mainly charts the role of the region in the Spanish-American War and the Cuban Missile Crisis.

Elsewhere, you’ll find several literary giants’ homes. Ernest Hemingway’s Key West home, where he lived in the thirties, is now a museum, as well as Tennesee Williams’ home of three decades. Both are quick visits and easy to squeeze into a busy schedule.

Fort Zachary State Park is another gem, home to the island’s only beach and the eponymous military fort used in the American Civil War and Spanish-American wars. The beach is also one of the best places to catch the sunset, although park rangers will briskly kick you out.

Of course, at night is when Key West comes alive. Its excellent array of bars, restaurants, and nightclubs make it far more lively than many of the other islands – perfect for letting loose after a long day's sightseeing. There’s even a thriving LGBT scene, with drag shows and gay bars centered around the famous Duval Street area.

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Get out on (or under) the water

Heading to the Keys and not getting out on the water is a chance wasted. While it’s widely regarded as the premier destination for sport fishing, there’s more than ample opportunity to experience the staggering breadth of diversity in the Keys’ surrounding seas.

If you’ve ever been interested in fishing, this is the place to be. Big game fishers from across the world swarm to the keys for the opportunity to catch some monster-sized fish like blue marlin and dolphin (dolphin fish, not dolphins). Of course, you’re unlikely to be after the big boys on a first try, but you can hop on a day-trip, learn the basics, and try to catch your first fish.

Scuba diving in the Keys is unmissable. The combination of perfectly clear water and sublime diving sites make it extra special. The Molasses Reef is the core of any diving trip, especially for first-timers, where you’ll likely see reef sharks, turtles, and some rays. Beyond that, multiple ships have been sunk deliberately and otherwise to offer a spectacular location. It’d be a great place to get your PADI certificate!

From there, you can expect all the usual suspects – parasailing, paddle boarding, jet skis, and the like. Many companies offer all of the above, so sift through and use reviews and personal judgment to decide the best option.

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Meet the locals

Not Bill and Betty from Boston down for the winter – meet the wilder locals that have made the Keys their home for far longer than anyone else.

With the sea intrinsically tied to the region, it’s the perfect location for conservation centers. At the top of the list is The Turtle Hospital. The center takes in injured turtles and rehabilitates them before sending them back into the wild. You’ll enjoy a tour, meet some patients, and feed some nearly-ready turtles before they head home.

The Dolphin Research Center is another excellent day out. The center houses dolphins that cannot be released into the wild because they were born in captivity, have been rescued from elsewhere, or are too severely injured. The center works with the dolphins to help them live as enriched a life as possible and let visitors in to see the work.

Other top attractions include the Key West Butterfly Conservancy, and the Florida Keys Wild Bird Center. As a bonus, you can also head down to Robbie’s Marina on Islamorada and feed the enormous tarpon swimming around the docks.


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Private Islands and waterside hideaways

Options are boundless in the Florida Keys. High-end private island resorts, boutique hotels, and mesmerizing waterfront homes are just some of the possibilities. The type of trip you’re on is as important as anything when deciding where to stay, so consider what you plan to see while you’re there.

Things can get pricey here, though. Especially in the high season, so be prepared to forgo on the more luxurious side of things if you want to save a penny or two.

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Image: Ocean Edge Key West

Our Top Pick: Ocean Edge Key West

Stock Island, Florida Keys
$$$ | See inside

This stunning little property sits on Stock Island, the next island up from Key West. With its own marina, six swimming pools, ocean access, and a range of activities, Oceans Edge is the perfect place to do it all.

Comfortably within striking distance of the delights of Key West, but a little quieter and more secluded, its rooms come with sea views, and its beautiful restaurant is a delight for breakfast, lunch, or dinner over the marina. Luxurious and homely all in one.

Book Your Stay

Other Top Picks


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Seafood, eat food

You’re in the Florida Keys. If you don’t like seafood, it’s time to come around to the idea. Some of the best and freshest catches are available on your doorstep during a visit, and not indulging in some conch fritters is borderline madness.

Of course, you can’t skip Key Lime pie, either.

Our Top Pick: The Fish House

Key Largo, Florida Keys
$$$ Menu

A true staple of the Florida Keys and one of the first you’ll even stumble across as you arrive, the Fish House serves no-frills seafood in delectable piles on your plate. Think Florida lobster, stone crab, mahi-mahi, chowders, conch, or grouper, among others.

As they source directly from the local fisherman, it’s not a guarantee you’ll have your favorite fish on the menu, but rest assured, knowing that whatever is coming from the kitchen will be excellent.

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The Best of the Rest


P.S. Check out 6 of the best side hustles to make extra cash for your next trip*

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