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Cool and unusual things to do in the Florida Keys

There are many cool and unusual things to do in the Florida Keys and Key West. The USA’s most southerly region is very close to the Caribbean and had not only great weather, but great Florida Keys tourist attractions, like the Turtle Hospital, Mallory Square Sunset Celebration, the African Queen boat, author Ernest Hemingway’s house and the southernmost point of the continental United States. Check out our Florida Keys tips and map of the best places to visit in Florida’s popular region.

There are some places we go to where we already have preconceived ideas of what we’ll find. Despite there being countless unusual things to do in the Florida Keys and Key West, it remains one of those destinations.

Firstly, there’s the weather in the Florida Keys. The most southerly stretch of the Sunshine State is spoilt with many days of sunny rays. And with the tip of Key West just 90 miles from Cuba, it’s a very tropical climate.

With that, you’d perhaps expect a laid back Caribbean atmosphere. But the Keys delivers this and more. Locals seem to become ever more relaxed the further south you go, while Key West has evolved further with something of a go-it’s-own-way, quirky nature – crowned by the annual, anything-goes Fantasy Fest jamboree. But you don’t have to wait until autumn to enjoy a little of the Keys’ unique culture.

Then there’s the food – with around 1,700 islands of the Florida Keys and mile upon mile of coast, you’d expect the area to have excellent seafood. Not only will you find the freshest lobster, but also conch, a shellfish from which the locals have penned the Keys’ nickname – the Conch Republic. But don’t expect these seafood delicacies to be served in overblown restaurants sporting starched white tablecloths. Harbourside restaurants and sink-your-toes-in-the-sand beach dining is a thing here.

Cool things to do in the Florida Keys - catch dinner and the sunset at Marker 88, in Islamorada

Then there’s key lime pie – if there’s one thing you’d expect to find and, if you’re like me, will consume in huge quantities, it’s this local creation. It comes in ever more varieties, with each venue you visit claiming the crown to the best key lime pie in the Florida Keys. So with some preconceived ideas and expectations met, but with plenty more to discover, I present to you some of the best things to do in the Florida Keys and Key West.

Things to do in the Florida Keys Enjoying the sunset at Marker 88, in Islamorada

Cool and unusual things to do in the Florida Keys and Key West

1. Save the turtles

Unusual things to do in the Florida Keys - visit the Turtle Hospital in Marathon

Turtles are one of my favourite animals since I swam with these magnificent sea creatures in the Caribbean. So visiting the Turtle Hospital in Marathon was definitely one of my favourite things to do in the Florida Keys.

The hospital was set up in 1986 to carry out research and rehabilitation of injured sea turtles, returning many to the sea, or continuing to look after the animals for the rest of their lives.

Unusual things to do in the Florida Keys - the Turtle Hospital rehabilitates the animals and teaches us about them

It’s a fantastic centre for conservation and learning – perfect for adults and children.

2. Take to the water on the African Queen

Unusual things to do in the Florida Keys - explore the canals on the original African Queen

Relive a little movie history aboard the steamboat featured in the classic Hollywood film, The African Queen. The boat used to shuttle cargo, missionaries and hunting parties across the Victoria Nile and Lake Albert. Then in 1951 it was used as the namesake vessel in the Humphrey Bogart and Katharine Hepburn film.

Unusual things to do in the Florida Keys and Key West - take to the canals aboard the African Queen

Afterwards, she remained in service in Africa until 1968 when she was brought to the United States working in San Francisco, Oregon and Florida. Now you can take daily cruises on the iconic boat through the canals of Key Largo.

3. Become a rum runner

While on holidays to Florida Keys don't worry about getting caught while indulging in the local tipple - head to Key West's First Legal Rum Distillery

Become a (legal) rum runner at Key West’s first rum distillery. Chef, and acclaimed local restauranteur, Paul Menta, sought a new challenge in 2013 and founded the Key West Legal Rum Distillery. Housed in a former Coca-Cola bottling plant, the distillery produces six times distilled speciality rums with infusions of coconut, vanilla creme brulee and key lime.

Paul Menta of Key West First Legal Rum Distillery - another of the cool things to do in Florida Keys

If rum’s too strong for you, it also makes Key West sodas with unique, all natural flavourings like strawberry cream and ginger lime.

4. Get earnest with Hemingway

One of the world’s most popular novelists, Ernest Hemingway enjoyed a golden period while living in Key West. It’s here at the Hemingway home, that he wrote A Farewell To Arms and it’s thought that many of the characters in To Have and Have Not are based on Key Westers he knew at the time.

Unusual things to do in the Florida Keys - visit Hemingway House

Unusual things to do in the Florida Keys - visit one of the six-toed cats at Hemingway House

The Spanish colonial style building, now a museum to Hemingway’s craft, is also home to a menagerie of cats. The Hemingways were big cat lovers, nurtured by a white six-toed cat they were given by a ship’s captain. Today 40-50 six-toed cats live in the museum grounds, some thought to be descendants, named Snow White. Hemingway named all of his cats after famous people so you can meet any number of celebrity moggies at the museum.

5. Spot unusual breeds

Unusual things to do in the Florida Keys - see the feral chickens of Key West

The Florida Keys is home to a fantastic range of wildlife, on land and at sea. There are exotic birds, flamingos, butterflies, dolphins, and even the opportunity to feed giant tarpon – not to mention the six-toed cats of Hemingway house and museum. But Key West has some other amusing locals in a breed of wild chickens that roam its streets, running across the road in small pecky packs. I liked this quote about the feral fowl, that they seem the perfect metaphor for Key West – historic, colorful, sort of wild, a little noisy and occasionally annoying.

Unusual things to do in the Florida Keys - spotting Key deer pic Joseph C Boone

Another unusual breed you should try to spot – though it isn’t difficult as they roam residential streets is Key deer. Put spotting the deer on your list of things to do in the Florida Keys because they are an endangered species only found on the islands.

The fearless animals can be spotted feeding on grass verges and are very friendly. Also, Key deer are known to swim between the islands of the Florida Keys, which has to be worth seeing.

6. Catch an entertaining sunset

Cool things to do in the Florida Keys - enjoy the daily sunset celebration at Mallory Square, Key West

When I first heard about the Mallory Square Sunset Celebration I thought we’d arrived in Key West just in time for a special annual event. But it’s far better than that. It seems the people of the Conch Republic love a good sunset and sun-kissed Key West has a perfectly colourful ending to each day.

It’s not just the sunset either – the orange-pink painted sky that hangs over the Atlantic Ocean is a perfect backdrop to the colourful action on land. Mallory Square is the heart of Key West and each evening an array of street performers, jugglers, musicians and more line the promenade to entertain the masses – it’s one of the most colourful Florida Keys tourist attractions.

7. Go to the ends of the Earth

Unusual things to do in the Florida Keys and Key West - go to the southernmost point

Well, it’s not quite the end of the Earth, but I always love places that are geographical extremes. And at the very tip of Key West, you’ll find yourself at the most southerly point in the continental United States.

It’s a place to feel the sea breeze in your hair as you look wistfully across the ocean towards Cuba and beyond.

8. Have a drink at Sloppy Joe’s Key West

Things to do in the Florida Keys - call in for a drink at Sloppy Joe's Key West | pic: Ray LAC

Sloppy Joe’s is an iconic bar founded in 1933, although it moved to its present location in 1937. Among its most famous patrons were the novelist Ernest Hemingway and the infamous rum runner Habana Joe. Such is the bar’s status that it is also referenced in Orson Welles’ classic film, Citizen Kane.

Key West sees itself as a distinctive location and has a reputation for quirkiness. Locals even once declared Key West as a republic, seceded from and declared war on the rest of the USA. And at Sloppy Joe’s Key West you’ll find the embodiment of the area’s culture. Incidentally, one minute after declaring independence the Key Westers surrendered and demanded $1 billion in compensation. Yes, they’re an amusing bunch!

9. Fantasy Fest Key West

If you’re planning a trip to the Florida Keys it’s well worth heading there in autumn for the annual Fantasy Fest Key West held this year from October19-28. It’s a 10-day no-holds-barred street party for fun-loving grown-ups.

Meet all manner of characters at the Fantasy Fest parades - a cool thing to do in the Florida Keys | pic Cabayo

Beyond the expected drinking and dancing, the streets are filled with parades, serious costumes (or a lack of clothes altogether), plus body painting and you’ll find there are very few inhibitions there.

10. No Name Pub

The No Name Pub is not somewhere to be forgotten. It started out in the 193o’s as a general store, then a tackle and bait shop and even hosted a brothel. However, since the 1940’s it has been a pub and eatery.

I was fascinated by the place and loved that its walls and ceiling are plastered with dollar bills – it made for unusual decor.

Dollar bills hang from the ceiling of the No Name Pub - one of the unusual places to visit in the Florida Keys

Holidays to Florida Keys – how to get there

Flights from the UK

For those taking holidays to Florida Keys, you have plenty of choice of airports for flights departing the UK (driving distances below take you to Key Largo in the north of the island chain – note that Key West is still another two hours drive from there):

  • You can fly to Orlando Sanford or Orlando International Airport. It is a four to five hours drive from Orlando to the Florida Keys.
  • Flying to Key West International means landing into the biggest city of the Florida Keys, however, there are no direct flights from the UK.
  • You can also fly into Miami International. It is a 90-minute drive from Miami to the Florida Keys.
  • Tampa International airport is a five-hour drive from the Florida Keys.
  • Connecting at West Palm Beach International will require a stopover in the US first, and is roughly two and a half hours drive from the Florida Keys.
  • Fort Lauderdale International airport is just over two hours drive to the Florida Keys.

Where to stay in The Florida Keys and Key West

Where to stay in Florida Keys, this is sunrise from my accommodation at Amara Cay Resort, Florida Keys

The sun rises in the east and so an Atlantic Ocean facing room at the Amara Cay Resort, in Islamorada, is destined to impress. By day there’s watersports or just beach lounging to be had at this “barefoot elegance” resort. With a good restaurant (where I enjoyed my first taste of conch) and spacious accommodation, it has a great location at the heart of the Keys.

During your holidays to Florida Keys, embrace the Florida Keys lifestyle at Amara Cay

Enjoy plenty of chic at the boutique The Gates Hotel in Key West. A completely modernised and transformed former motel (the only sign of its past being the layout of the rows of accommodation set around the pool). But once in your room you’ll find a soothing mix of blue hues and sand colours, as well as extras like a coffee machine and a tablet to help you discover the local area. The hotel also has its own signature rum created by Key West Legal Rum Distillery.

Hotels in the Florida Keys - The Gates Hotel

Alternatively, search for more Florida Keys hotels below.

Map of the Florida Keys – our favourite places to visit

Discover more about the Florida Keys and other destinations set on US Route 1 in the DriveUS1 road trip – read the stories and see videos and more here.

On the islands of the Florida Keys - don't miss the sunset

Extra pics by Joseph C Boone, Ray LAC, and Cabayo used under Creative Commons 2.0.


LiveShareTravel's founder and editor Sarah, has long been passionate about luxury travel and, with a nose for a deal, has helped many friends book trips as affordable as they are stylish. As a journalist and travel magazine editor with expert knowledge of shared ownership, starting LiveShareTravel was a natural progression. She can't live without her smartphone, loves dancing (especially salsa), wine and massages; and is never happier than when she's wandering the world. She is co-author of The Luxury Traveller's Handbook.

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7 Responses to Cool and unusual things to do in the Florida Keys

  1. Florida Keys is somewhere we would love to go. It looks like such a great place to spend some time chilling in the sunshine. Visiting the Turtle Hospital would be on our list. Sounds like they do amazing work. This has some great tips and hopefully we can check them all out when we get there one day.

    • Yes, the Turtle Hospital is fantastic – it’s lovely to see the animals they’ve saved there, even better to hear the stories of the ones they’ve been able to return to the sea. Think you’ll really enjoy The Keys – these are just some of the unusual things you can do there, but you can also just layback on the beach, enjoy its great food and the laid back vibe of the locals!

  2. We visited Key Largo last September for a few days, and we are planning on coming again this Sept, and hopefully travelling to Key west too. Would love to see the Turtle Hospital, and Hemingway’s 6 toed cats 🙂
    We loved it so much last year.
    Wonderful place to be x x

  3. Helping to rescue the sea turtles is one of my favorite travel pastimes (I did it in Hilton Head and Cancun). I love those creatures so much! I’ll have to plan a trip to the turtle rescue center. I love all of your photos and now I’m craving Key Lime Pie. 🙂

    • Same! My first encounter was saving a tiny baby leatherback turtle in Barbados. It had only hatched that morning and the sun was coming up threatening to toast him on the beach so we made sure he got into the sea. They’re such adorable animals. Also, have you seen this one on swimming with turtles in St Vincent (one of my favourite experiences ever)? Thanks, glad you enjoyed the photos. Eat alll the Key Lime Pie when you get there!

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