10 Fun and Unique Things to Do in Key West, Florida

If quirky was a place, it would be Key West. From the free-roaming chickens to the curiosity shops on Duval Street, it’s honestly unlike anywhere else I’ve ever been to (in 47 countries and counting). 

That means it’s not too tricky to find fun and unique things to do in Key West, because just wandering around the Old Town is going to be an experience. That said, there are a few hidden gems that we stumbled on during our last visit that I’ve been dying to share. 

This quick island guide ticks off all the must-visit spots in Key West, with a few fun extras thrown in. I’ve also included some general info about where to stay and eat while you’re in town, but if you have any more specific questions, just let me know in the comments section! 

Top 10 Things to do in Key West 

1. Take a Cocktail Class or Tasting at a Rum Distillery 

This is one of those activities that I think a lot of people miss on their first (or even second or third) visit to Key West. But it’s so worth doing, especially if you’re a cocktail lover like me! It makes for a great activity if the weather isn’t cooperating too. 

There’s a high concentration of distilleries for such a small island, with about three to choose from.

That’s because rum has a long and colourful history in Key West, dating back to the days of Caribbean trading ships, pirates and Prohibition-era rum runners who smuggled alcohol through the Florida Keys. 

Today, that rebellious spirit lives on in the island’s thriving cocktail scene, and there’s no better way to experience it than with a rum tasting or cocktail-making class.

We did one at Papa’s Pilar at Hemingway Distillery, named after Ernest Hemingway’s beloved fishing boat. Housed in a historic tobacco warehouse in Old Town, the distillery offers guided tours, rum tastings and hands-on mixology classes where you can learn to shake up your own tropical cocktails. 

It’s a brilliant way to spend an afternoon, especially if you fancy swapping the beach for something a little different. There’s also a cool tour you can do which includes admission to The Ernest Hemingway Home and Museum as well as the distillery, and includes three rum cocktails along the way.

Book it here.

2. Catch a Movie at the Tropic Cinema

The Tropic Cinema looks like something out of a movie itself, with its retro neon sign and bubblegum-coloured exterior. Most people simply snap a photo of the cinema if they happen to pass by, but catching a film there is where the fun really begins. 

The vintage vibes continue indoors, and they’re usually showing a good mix of old classics and new releases. 

Another great option for a rainy afternoon or if you want an evening off from the wild nightlife that Key West is known for. Speaking from personal experience, our second night in Key West required some serious quiet time after getting a little out of hand on night one. 

If you happen to be in town in November, you might even catch the Key West Film Festival, with screenings across multiple venues including the Tropic Cinema and the San Carlos Institute. A must for movie buffs! 

See the latest screenings at Tropic Cinema here. 

3. See Mile Zero and the Southernmost Buoy 

Key West is famous for lots of things, one of which is that it marks the southernmost point of the continental US. In true Key West style, this fact is celebrated with a colourful buoy at the southern end of Duval Street. 

There’s not too much to see here, but it’s worth dropping by just to say you’ve been there.

We also went to Mile Zero, which marks the starting point of the famous US Route 1 and the Overseas Highway. From there, this road stretches all the way over land and sea to Fort Kent in Maine. 

There’s a cute little souvenir stand here selling conch shells and other bits and bobs, so it’s well worth stopping by on one of your strolls through town. 

4. Visit the Ernest Hemingway Museum or Little White House 

Key West is a one-of-a-kind place with the backstory to match, and two of the best places to discover it are the Ernest Hemingway Home and Museum and the Harry S. Truman Little White House. 

Hemingway lived on the island throughout the 1930s, and his beautiful Spanish Colonial-style home is now open to visitors. You can wander through the rooms where he wrote some of his most famous works, explore the tropical gardens and meet the resident six-toed cats, many of which are descendants of Hemingway’s original pet. 

Alternatively, the Little White House offers a glimpse into Key West’s presidential past. Once used as a winter retreat by President Harry S. Truman, this historic property has welcomed several American presidents and important political figures over the years. 

I’d recommend taking a guided tour to hear the stories behind the house and see its beautifully preserved interiors.

5. Browse the Boutiques on Duval Street

No list of things to do in Key West would be complete without a wander along Duval Street, the island’s famous mile-long strip of colourful shops, restaurants and live music bars. 

While it’s best known for its nightlife, there’s plenty to explore during the day, from independent clothing boutiques and jewellery shops to quirky souvenir stores and galleries selling locally inspired artwork.

I particularly love browsing the smaller shops tucked between the bars, where you’ll find everything from tropical homeware and handmade accessories to vintage-style clothing. It’s the perfect place to pick up a little something to remember your holiday by, although I’d recommend exploring the quieter side streets too if you’re after something more unique.

Some of my favourites are Besame Mucho, for artisanal jewellery, homewares and fragrances, and The Green Pineapple, which is perfect for picking up some quality linen islandwear. 

6. Soak Up the Sunset Celebrations at Mallory Square 

Of all the Key West experiences you absolutely shouldn’t miss, it’s the famous Sunset Celebration at Mallory Square. 

Every evening, locals and visitors make a beeline for the waterfront to watch the sun dip into the Gulf, accompanied by street performers, musicians, artists and food vendors. It’s lively, a little eccentric and one of those fun traditions that just screams Key West. 

I’d recommend arriving around 45 minutes before sunset to soak up the atmosphere and find a good viewing spot along the water. 

Grab a drink (we got takeaway frozen cocktails from Flying Monkey’s Saloon), watch the performers and toast to the sun kissing the sea goodbye. Yes, it’s touristy, but in the best possible way, and I genuinely think it’s one of the most memorable, free things to do in Key West.

7. Take a Trolley or Conch Train Tour 

For those with kids or even just first-time visitors, a Trolley Tour or Conch Train tour is a brilliant way to get your bearings while learning a little about the island’s history. Again, it’s a little touristy, but the little trains somehow suit Key West’s character perfectly. 

Both take you past colourful historic houses, famous landmarks and some of Key West’s most interesting neighbourhoods, with tongue-in-cheek commentary along the way.

The Conch Tour Train is particularly iconic, having shown visitors around Key West since 1958, while the Old Town Trolley offers the added flexibility of hopping on and off at designated stops. I’d recommend doing one of these tours early in your trip, especially if you’re only staying for a couple of days. 

It’s a great way to spot places you might want to return to and saves your feet in the Florida heat!

8. Shop for Local Art at the Galleries

Key West has attracted artists and creative types for decades, so it’s hardly surprising that the island has a thriving art scene. 

Spend an afternoon wandering through the boutiques around Duval Street, Whitehead Street and the surrounding Old Town, where you’ll discover everything from colourful tropical paintings and contemporary photography to handmade ceramics and quirky sculptures.

One of my favourite things to do on holiday is to hunt for a piece to take paradise home with me. 

And here, the artwork really captures the island’s personality, with pastel-coloured cottages, palm trees, turquoise waters and those famous Key West sunsets. 

Look out for galleries around Gallery on Greene and the creative studios at The Studios of Key West, which also hosts exhibitions and events. Even if you’re not planning to buy anything, browsing the galleries is a lovely way to spend a slower afternoon.

9. Swim and Sunbathe at Smathers Beach 

If you’re craving a proper beach day, Smathers Beach is one of my favourite places in Key West. 

Stretching for around half a mile along the island’s southern shoreline, it’s the largest public beach in Key West, with soft sand, swaying palm trees and gorgeous turquoise water. It’s particularly popular for swimming, sunbathing and watersports, with equipment rentals available nearby.

I’d recommend visiting in the morning when it’s generally quieter, and the temperatures are a little more comfortable. Bring a towel, find yourself a spot beneath the palms and enjoy a few hours getting lost in a good book.

10. Take a Sunset Sailing Trip or Wildlife Watching Boat Trip

Getting out on the water is one of my absolute favourite things to do in Key West, and there are some fantastic boat trips to choose from. 

For a romantic experience, I’d recommend booking a sunset sailing cruise, where you can watch the island’s famous sunset from the water, with drinks and music included. 

But there are everything from party-centric tiki sandbar safaris to smaller, more intimate sailing trips, so you can choose whichever suits your style.

If you’d prefer something a little more adventurous, opt for a wildlife-watching or snorkelling excursion instead. The waters surrounding Key West are home to dolphins, sea turtles, tropical fish and beautiful coral reefs, and there’s nothing quite like jumping in and spotting them with your own eyes. 

Try this dolphin-watching trip that combines wildlife spotting with snorkelling in the electric-blue waters of the Florida Keys. 

Things to do in Key West: FAQs

Is Key West worth visiting?

Absolutely! Key West is one of my favourite places in Florida for its laid-back Caribbean atmosphere, colourful historic houses, lively bars and incredible sunsets. 

There’s something wonderfully quirky about this little island, from the pottering chickens to the legendary nightlife along Duval Street. If it’s a chilled-out vibe you’re after with some fun culture thrown in, Key West is definitely worth adding to your Florida itinerary.

What are the most romantic things to do in Key West for couples?

For couples, I’d highly recommend booking a sunset sailing cruise, preferably with a glass of champagne in hand. 

Other romantic things to do in Key West include wandering the pastel-coloured streets of Old Town, enjoying a candlelit dinner at Nine One Five or Bagatelle, and spending a lazy afternoon at Fort Zachary Taylor Historic State Park. 

For something extra special, you could even book a private boat charter or take a seaplane trip to Dry Tortugas National Park.

What are the best beaches in Key West?

Although Key West isn’t particularly famous for its beaches, there are still some lovely spots to enjoy the Florida sunshine. 

Fort Zachary Taylor Beach is my top recommendation for its clear water, snorkelling, and beautiful natural setting. Smathers Beach is the largest sandy beach, ideal for sunbathing and watersports, while Higgs Beach has a more relaxed, local atmosphere. Just be aware that some beaches can be rocky, so water shoes are worth packing. 

What to do in Key West, Florida if it’s raining?

A little rain doesn’t have to ruin your Key West holiday! I’d use the opportunity to explore the island’s indoor attractions, including the Ernest Hemingway Home and Museum, Truman Little White House, or just catching the latest blockbuster at the Tropic Cinema. 

Alternatively, settle into a cosy cafe for a slice of Key lime pie, browse the independent shops along Duval Street or enjoy a leisurely lunch at one of the island’s fantastic seafood restaurants. Tropical showers can pass surprisingly quickly, so you might still get some sunshine later in the day.

How to get to Key West?

There are several ways to reach Key West, but I recommend driving from Miami along the Overseas Highway. 

The journey takes around 3.5-4 hours without significant traffic or stops, crossing a series of beautiful islands and bridges with incredible ocean views. We hired a convertible Mustang from Miami Airport for a bit of fun, and it was surprisingly reasonable!

Alternatively, you can fly directly into Key West International Airport, which is just a short drive from Old Town, or take the Key West Express ferry from Fort Myers Beach or Marco Island. If you’re planning a Florida road trip, the drive through the Florida Keys is an experience in itself. 

What are some good things to do in Key West with kids?

Despite its reputation for nightlife, Key West is surprisingly family-friendly. 

Little ones will love spotting colourful butterflies and flamingos at the Key West Butterfly and Nature Conservatory, meeting marine creatures at the Key West Aquarium and discovering the famous six-toed cats at Hemingway’s former home. 

I’d also recommend taking the Conch Tour Train around Old Town, spending an afternoon at Smathers Beach or visiting Truman Waterfront Park for its playground and splash pad. For older children, a dolphin-watching or snorkelling excursion is another fantastic option.

Still on the search for more cool things to do in Key West? Let me know what your travel vibe is in the comments! I’d love to give you a personal recommendation.