Diving into… Key West, Florida

In the latest instalment of his popular Diving into… series for The European, ultra-endurance swimmer and columnist Ben Hooper swaps cold currents and wetsuits for the sun-drenched waters, coral reefs, and easy-going charm of Key West, Florida — where open-water swimming meets island life in technicolour

There are swims, and then there are Key West swims. The sort that starts with a sunrise the colour of coral and ends with you floating on your back wondering if you’ve accidentally drifted into a postcard. At the far end of the Florida Keys, where the Gulf of Mexico and the Atlantic Ocean swim together, Key West is the southernmost point of the continental United States and quite possibly the most relaxed place I have ever visited.

Here, at the end of the famous seven-mile bridge and visually stunning Route One, the water running to the horizon is a warm turquoise, the cocktails taste colder, and best of all, the locals have perfected the fine art of taking things slow. For open-water swimmers, this island is paradise: no wetsuits, no icy shocks, no gritted teeth — just clear, calm seas and a sense that life really can be as easy as it looks on the postcards.

So, leave your neoprene behind, grab your goggles, and prepare to dive into a world of salt, sunshine, and just a hint of mischief in the ‘American Caribbean.’

Welcome to Key West, Florida… History, Interesting Facts, and Weather

Key West’s story is one of defiance, artistry, and sun-bleached charm. It’s been home to pirates, native Americans, poets, wreck salvagers, and even presidents. In 1982, when the U.S. Border Patrol set up a roadblock at the entrance to the Keys, the locals responded by declaring independence, forming The Conch Republic in mock protest. They still celebrate it every April, complete with parties, flags, and enough Cuban rum to fuel a small navy.

Cuba lies a mere 90 miles to the south, and the island’s Cuban influence runs deep. From the aroma of cigars to the rich coffee and music spilling into the streets. And, of course, their famous pulled pork and roaming cockerels, which, incidentally, it is a felony to run over with your car or catch, kill and cook for Sunday lunch.

For swimmers however, the climate is gloriously consistent: 26–32°C air temperatures most of the year, with sea temperatures rarely dropping below 24°C. The rainy season (June to November) brings warm showers and the occasional storm, waterspouts and even an occasional hurricane which brings with it, hurricane parties!! April and May brings us “no see ‘ems” – bugs that bite you covertly, only feeling it a day later. Then there is lightning season, nature’s fireworks which are simply awesome. But between December and May, the island is pure gold.

Key West isn’t just about beaches, it’s a coral cay, part of a delicate marine ecosystem. The surrounding waters are protected by the Florida Keys National Marine Sanctuary, home to sea turtles, parrotfish, and coral gardens that look like they were designed by an overzealous artist. Simply stunning. Colourful, like Duval Street, which at night becomes a vibrant atmosphere, the street running north to south for over a mile, it connects Sunset Pier and the Gulf of Mexico to the Atlantic Ocean and all the people in between. This is the LGBTQIA+ home of the Southern States… A safe and great night out for all!

Check out these swim locations – with caution…

Smathers Beach

A golden ribbon of soft sand and calm water, Smathers is Key West’s largest and most accessible beach. At two miles long, it offers space for relaxed swimming, snorkelling, and people-watching (there’s always one tourist attempting to paddleboard while holding a margarita).

Early mornings are best for mirror-smooth seas, the scent of salt and sunscreen, and the odd pelican gliding low overhead. The water ranges from 25–30°C, so you can leave the wetsuit at home. Stay within the buoy line, watch for light currents at the eastern end, and keep an eye out for friendly sea turtles and do not touch any coral you encounter. You may even see the odd shark, as I did. Friendly but awesome in their spectacle. Oh, and did I mention someone I met there once – I called him “Geoff.” A 10-feet long Salt-water Alligator. I assume he was, I did not get close enough to interrupt his sunbathing on the distant rocks. Either way, beautiful and as big as a Ford pick-up truck.

Dry Tortugas National Park

Accessible only by ferry or seaplane, this chain of seven small islands lies 70 miles west of Key West. It’s a slice of wilderness wrapped around Fort Jefferson, a 19th-century fortress surrounded by blindingly turquoise water.

Swimming is permitted in designated areas, though many combine a dip with snorkelling over coral reefs teeming with life. The visibility is astonishing — you’ll see angelfish, coral fans, and perhaps even a barracuda (keep your cool; they’re just curious).

Bring your own water and shade — this is swimming at its most elemental and remote.

The Round the Island Swim (Annual Key West Swim Around the Island)

Each June, hundreds of open-water enthusiasts take on this legendary 12.5-mile swim in a clockwise circumnavigation of Key West. It’s a bucket-list event and it’s not for the faint-hearted, but beautifully organised, with safety boats, kayakers, and cheering locals.

Expect shifting currents, warm waters, and a feeling of immense satisfaction as you finish back at Smathers Beach. Relay and solo entries available — and yes, bragging rights for life. Just ensure you get your timings right for passing under the famous bridge… I will leave you to research this swimming delight.

Higgs Beach

A favourite among locals, Higgs Beach offers calm conditions, sandy entry points, and a 400-metre swim zone perfect for laps or leisurely floats. Facilities include showers, cafés, and sun-loungers shaded by palms.

Watch for the occasional jellyfish, but otherwise it’s as serene as open-water swimming gets and when you’re done, wander to the nearby garden club for a quiet post-swim stroll.

Islamorada – Founders Park Beach

An hour north of Key West, in Islamorada (the “Village of Islands”), Founders Park offers a wide, sheltered bay ideal for training swims. The park charges around $8 entry and includes lifeguards, showers, and restrooms. The homes are luxurious and to die for, with a 7-figure price tag and a film-set for Netflix and Hollywood.

It’s popular with triathletes and locals alike, and if you’re lucky, you may spot dolphins keeping pace. They’re faster. Accept it gracefully.

Attractions to visit…

1. Ernest Hemingway Home & Museum – Entry $18. Literary history meets feline royalty. Hemingway’s famous six-toed cats still wander the shaded verandas as if they own the place (which they do). Worth the visit for the writing studio alone.
2. Mallory Square Sunset Celebration – Free and unmissable. Jugglers, musicians, and sunset-watchers gather nightly to toast the day’s end. Bring a drink and your best “I live here now” face, and maybe a loved one for the romance.
3. Fort Zachary Taylor Historic State Park – Entry $6 per car. Civil War-era fortifications meet some of the island’s best snorkelling waters. Bring reef shoes and curiosity and do not forget to check out the cannons!
4. Butterfly & Nature Conservatory – Entry $15. Step into a fluttering cloud of butterflies and exotic birds. Calming, colourful, and about as close to floating in air as you can get – this is mindfulness personified.
5. Southernmost Point Buoy – Free, but with queues. The symbolic “end of the road” and a rite of passage for visitors. Bring patience and sunscreen and heads up, if it is stormy or hurricane battered, the waves will swamp you, the Buoy and the street beyond.

Insert image of Ben standing under palm trees by the sea) with the cap: Soaking up the Key West sunshine: where the Gulf meets the Atlantic, and time itself seems to slow to island pace. Credit: Supplied

Hidden Gem Attraction – Key West Garden Club at West Martello Tower
Free entry (donations are welcome though). A peaceful, flower-filled hideaway within the ruins of a Civil War fort. Stroll among orchids and bougainvillea, sea breeze in your hair, and not a selfie stick in sight. Peace…

Where to eat…

• Blue Heaven (Petronia Street) – A Key West icon. Breakfast under banyan trees while roosters strut by. Try the lobster Benedict or the banana pancakes and thank me later. Around $25–$35 per person.
• Louie’s Backyard (South Street) – Elegant but not stiff. Caribbean-inspired seafood, oceanfront terrace, and service as smooth as the local rum. Mains $30–$45.
• Garbo’s Grill (Caroline Street) – A converted food truck that’s become a legend. Try the mahi tacos or Korean BBQ burrito for under $20. Casual, flavourful, brilliant.
• The Hot Tin Roof – Still humming with music, laughter, and a touch of Key West eccentricity. Live bands, cold drinks, good company. Perfect for a relaxed night of island rhythm and people-watching and with the sunset, romantic on the ocean’s watch.

Hidden Gem Eatery – Sandy’s Café (White Street)
This Cuban café tucked inside a laundromat serves the best Cuban sandwich in town — crispy, melty, divine. Breakfast under $10. Real food for real swimmers.

Dessert & Decadence – Better Than Sex Dessert Restaurant
Yes, it’s really called that — and yes, it’s worth it. Plush red furnishings, candlelight, and desserts with names like “Peanut Butter Perversion” and “The Tongue Bath Truffle.” Cheesy as only the US of A can do but still, a touch of erotica. Expect $15–$20 per dessert, and the atmosphere so sultry you’ll leave blushing. Book ahead; romance and mischief guaranteed.

Where to stay…

• The Ocean Key Resort & Spa (High-End) – Rooms from $550 per night. Overlooking Mallory Square, this five-star escape offers private balconies, infinity pools, and cocktails delivered faster than you can say “paradise.” Pros: sheer indulgence. Cons: you’ll never want to check out.
• The Marker Key West Harbor Resort – Mid-range luxury from $350. Pros: central location, chic pools, harbour views. Cons: nightlife nearby can hum late.
• Kimpton Fitch Lodge – A smart boutique accommodation, with prices from $200. Friendly staff, free bikes, small but stylish rooms.
• Heron House – Adults-only B&B from $180. Quiet courtyards, lovely breakfast, no children, no chaos.
• Boyd’s Key West Campground (Budget) – From $70 for a tent pitch, $120 for RVs. Ocean views, friendly vibe, and the occasional rooster alarm clock. Stock Island, an interesting stay and perhaps lacking the vibrance of downtown.

Water sports and Scuba Diving Options

If you can tear yourself away from swimming, the waters around Key West are a paradise for aquatic adventures.

• Key West Reef Snorkel & Dive Trips – Several operators run daily tours and PADI courses, running out to the Florida Reef, the only living coral barrier reef in the continental U.S. Expect coral gardens, parrotfish, and perhaps a passing sea turtle. Full-day dives from around $120, snorkel trips from $60.
• Paddleboarding and Kayaking – The mangrove tunnels off Stock Island and Sugarloaf Key are superb for gentle exploration. Half-day rentals from $40. Perfect for rest days (or so you can pretend you’re “cross-training”).
• Jet Ski Tours – For when you tire of doing the work yourself. Guided 90-minute tours circling Key West from $140 per person. Equal parts thrill and spray.

Other things to explore in the region include…

The obvious: reef trips, Duval Street nightlife, the ferry to Dry Tortugas.
The lesser known: Bahia Honda State Park, an hour up the Keys, boasts postcard-perfect sands and some of Florida’s calmest, most beautiful swim spots. Or visit No Name Key — home to the tiny, endangered Key deer, who wander freely and seem just as curious about you.

In Summary…

Key West is more than a destination; it’s a state of mind — salt-streaked, sun-drunk, and blissfully laid-back. The swims here don’t test your limits so much as expand your idea of joy. Unless of course, you compete in the Round-Island swim (bring your sunscreen and salt protection). My first plunge at Smathers Beach turned into a slow float, gazing up at circling pelicans and wondering how anyone ever leaves this island. My swim training ten-years ago and this year, to celebrate, only refills my heart with the joy and sunshine of the Conch Republic.

The food will tempt you and the sunsets will stop you, mid-sentence, and the sea will have you plotting your next visit before you’ve even towelled off. The people are as kind and relaxed as the tranquil settings you will indulge in. Visit between November and May for the most stable weather and the perfect excuse to combine swims, seafood, and a slice (or three) of Key lime pie.

Ben’s Open Water Swim Safety Tips:

1. Always swim within buoyed zones — boat traffic can appear faster than you think.
2. Stay hydrated before and after (rum punch doesn’t count).
3. Use reef-safe sunscreen — protect the ocean that protects you.
4. Watch for sharks, jellyfish and coral — admire, don’t touch.
5. If thunder rumbles, get out. Florida storms move fast.
6. Swim early or late; the midday sun can be brutal.
7. Use a tow float and bright swim cap for visibility.
8. Respect currents — ask locals before longer swims.
9. Avoid swimming after a heavy night at The Tin Roof.
10. Smile — you’re in paradise. Act like it.
    
    

Ben Hooper made global headlines with his bid to swim every mile of the Atlantic Ocean — a challenge Sir Ranulph Fiennes OBE called “the last great bastion to be conquered.” His four-month, 2,000-mile route from Senegal to Brazil, known as Swim the Big Blue, was derailed mid-Atlantic after his support vessel was damaged by storms, despite him surviving a near-fatal encounter with thousands of Portuguese Man O’War tentacles. He remains the only person with a WOWSA-verified attempt at the feat. Follow him on Instagram and X @TheBenHooper or visit www.thebenhooper.com

READ MORE: ‘AI can’t swim — but it might save those who do‘. As open-water swimming surges in popularity, endurance athlete and journalist Ben Hooper explores how artificial intelligence is transforming safety, training, and awareness — from lifeguard drones to data-driven goggles — while questioning whether technology can coexist with the soul of swimming.

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