10 Things to Do in Key West at Night

The Florida Keys' most vibrant nightlife is concentrated in Key West. From rum runs to sunrise parties and the world's most breathtaking sunsets, the island offers an endless summer - find out more!

Carla Yaquer

Carla Yaquer

9 min read

10 Things to Do in Key West at Night

Key West | ©Cayobo

The islands around Florida are famous for their lively nightlife full of lively spirit, good drinks and activities for all tastes. Among the 1,700 islands in the area, the iconic Key West or Key West, former US President Harry S. Truman's favourite island, shines.

It won't be hard to find a terrace or bar to have a beer, go kayaking, surround yourself with ghosts and ghouls, drink rum like Hemingway liked, or even go up to a Tiki Bar. The best things to do in Key West at night are varied and have something for everyone. Let's take a look at the must-do activities in this Caribbean-accented paradise.

1. Taste some craft beers at Duval Crawl

Duval Crawl| ©clesage1
Duval Crawl| ©clesage1

A stroll down Duval Street takes in most of the island city's main attractions. With so many bars and pubs lining this main street, you could spend the whole night visiting each one to sample the best beers and rum-based cocktails, such as the legendary Caribbean Breeze. Alternatively, to make the most of your visit, you can book a Key West pub crawl to explore the island's most iconic bars.

Immerse yourself in the buzzing beer scene at the Duval Crawl in Key West. This street becomes the perfect setting to explore the diversity of craft beers in a vibrant, colourful and festive atmosphere full of nightlife.

Each pub along this iconic main street offers a unique selection of beers, from the most local and authentic to the most innovative creations. From the Sunset Pier, with its privileged sunset view and live music, to the classic Sloppy Joe's, the bar that recalls Hemingway in its rum drinks. The experience is unforgettable. Discover the richness of flavours at each stop and soak up the magic of the night on the Duval Crawl.

Book a pub crawl in Key West

2. Ride the Ghost & Haunted Tramway

The Key West Sightseeing Tramway| ©Wendy Berry
The Key West Sightseeing Tramway| ©Wendy Berry

You may be surprised to learn that Key West, with its year-round sunshine and beautiful palm trees, is also known as one of the most haunted cities in the United States. The haunting spirits of pirates, Civil War soldiers and broken-hearted lovers are said to haunt everything from mansions to lighthouses here, creating an eerie atmosphere that can make even the bravest souls shiver.

But don't worry, you don't have to face these spooky places alone - when you book a ghost tour, you'll be accompanied by a group of experts who will recount the legends of each location with a touch of humour, and what's more, you'll do so aboard a themed tram. You'll be taken through the winding streets of the old town, making several stops including the Marrero House, the Porter Mansion, the cemetery and the oldest house in Key West, where you can still hear the footsteps of Captain Watlington.

Finally, don't forget to stop by some of the best museums in Key West such as the Shipwreck Treasure Museum and the Martello Museum of History and Art Gallery, also known as the Fort East Martello Museum, home to the legend of Robert Eugene Otto and his diabolical doll Robert, brought to life every night.

Book a ghost tour

3. Sail on a sunset cruise

Cruise on a sunset cruise| ©Miguel Discart
Cruise on a sunset cruise| ©Miguel Discart

Key West boasts one of the best sunsets in the world. You'll be able to capture the breathtaking views of the sun setting behind you as you float 'in the middle' of the ocean. The hazy tangerine and golden hues of the setting sun reflecting off the water create an indescribable and unforgettable spectacle.

When you book a sunset boat tour, the ship's captain will take you to see the city from a different perspective. From the iconic Key West lighthouse to Fort Zachary Taylor Historic State Park, more commonly known as Fort Zachary.

Another attraction of this type of tour is the opportunity to see dolphins jumping and frolicking in the setting sun. Other services such as champagne, wine and special amenities for couples are often included.

4. Sweeten your palate with Florida's best lemon tart

Key lime pie| ©Grete Howard ARPS
Key lime pie| ©Grete Howard ARPS

Key lime pie is the official dessert of the Florida Keys. According to Forbes, the recipe is Florida's contribution to the American sweet scene. If you're in the mood for a sweet treat, book a food tour and then indulge your taste buds with this gods delicacy with the authentic original flavour.

You can visit Better Than Sex, a dessert restaurant that opens its doors from 18:00 hours to sweeten up its diners in the evening. Its extensive menu of decadent desserts features key lime pie, along with other classics such as bread pudding, chocolate cake, biscuits and more, in a setting that's bursting with red velvet. This dessert-focused restaurant also has an incredible wine, beer and cocktail list to match the sweet treats.

El Mason De Pepe is another recommended restaurant. Located in Mallory Square, it is so close to Cuba that the 'Lime Pie' is written in Spanish on the menu; ask for it as: 'Torta de limón'. To close the top 3, we mustn't forget Key Lime Pie Bakery who write the phrase 'the original' on their façade, making it clear that their recipe is the classic that has conquered hearts around the world.

Book a food tour

5. Head to Mallory Square for the Sunset Celebration

Sunset Celebration| ©SridharSaraf
Sunset Celebration| ©SridharSaraf

The Sunset Celebration at Mallory Square is a popular event that many consider the gateway to Key West's nightlife scene. This event takes place nightly on the Mallory Square waterfront, and attracts a variety of local performers such as musicians, magicians, illusionists, musicians and street performers, who entertain audiences with their skills and creativity.

As well as being entertained by these local performers, visitors can also enjoy the delicious food served from the food trucks parked in the square. Some of the most popular delicacies include guacamole, conch fritters, chimney cakes, pineapple drinks and other tropical delicacies.

Many people stop by the food carts for a quick bite to eat before joining the pub crawls around Key West, with the plan to drink and dance. Mallory Square's Sunset Celebration is an excellent opportunity to enjoy music, food and local traditions while watching the sunset.

Book a pub crawl in Key West

6. Go moonlight kayaking

Kayaking by night| ©Movement Spontaneous
Kayaking by night| ©Movement Spontaneous

Your visit to Key West buys you an adventure and water sports pass almost without thinking about it. In this archipelago you can snorkel around the barrier reef, experience parasailing, cruise the Gulf of Mexico on a jet ski tour and kayak at night.

Experience the magic of Key West by kayaking in a glass-bottomed kayak at night. You can choose between single or double kayaks, all equipped with lights. This immersive, slow-paced and relaxing experience will take you through narrow mangrove tunnels and over shallow waters, home to nearly 400 types of marine life. Don't miss out on this sporting adventure, perfect for a family trip to Key West.

Buy a water sports and adventure pass

7. Take Hemingway's Rum Tour

Ernest Hemingway's House| ©Roger W
Ernest Hemingway's House| ©Roger W

Ernest Hemingway had a fascination with the daiquiri ever since he tried it in Key West. This rum-based drink became an icon of Key West, where every night this distilled sugar cane spirit enlivens the environment and envelops locals and tourists in a festive atmosphere.

Be sure to stop by Sloppy Joe's Bar where the party starts early, with free guided tours at their Key West First Legal Rum Distillery, strategically located near Mallory Square.

Alternatively, immerse yourself in the unique philosophy of Papa's Pilar, where they capture the adventurous spirit of Ernest Hemingway in every bottle of rum. Located near Mallory Square on Simonton St. Key West, here you can explore rum's rich history and indulge your senses with their cocktail-making classes, which have become the rum world's hottest show.

Book a Key West Pub Tour

8. Visit Key West's own little corner of Hollywood

Key West Theater| ©Edgar and Ron - Busy
Key West Theater| ©Edgar and Ron - Busy

Join the vibrant Hollywood nightlife scene by strolling down Eaton Street. One of the most fun things to do in Key West at night is to catch a live performance at the iconic Key West Theater on Eaton Street. This theatre hosts a wide variety of performances, including musicians such as John Hiatt, The Wallflowers, Ben Harrison, tribute and cover bands, and comedians. It is the perfect place for those who prefer a more relaxed atmosphere to the noisy nightclubs.

Another entertaining activity to add to your list of nightlife experiences in Key West is a visit to the Tropic Cinema on Eaton Street. This retro-style cinema shows blockbusters, independent films, cult classics and features state-of-the-art digital projection, neon lighting and comfortable seating.

The cinema also has a fascinating art gallery that you can explore for free, and the art deco design of the cinema itself is impressive. And if you're hungry, you can grab a beer, wine, coffee and delicious popcorn made with real butter at the bar. Tropic Cinema also hosts cultural events and lectures on the art of filmmaking throughout the year to stay on the cutting edge of Hollywood.

9. Cycle around the Historic Seaport

Sunset at Mallory Square.| ©Debbie Bergin
Sunset at Mallory Square.| ©Debbie Bergin

Embark on an exciting evening ride exploring Key West's Historic Seaport by bicycle. Either on your own or by booking a bike tour with a local guide, you'll immerse yourself in the history and beauty of the island as you pedal to the highlights. The tour will take you to Mallory Square, where ocean views blend with the vibrant atmosphere and spectacular sunsets that characterise this tourist destination.

Continue to Mile Marker Zero, marking the beginning of the iconic US1 highway. Here, capture the commemorative moment and the iconicMile Marker Zero sign. Afterwards, head to the stunning White Street Pier, a pier offering panoramic ocean and coastal views, ideal for strolling and enjoying the evening breeze.

Conclude your ride by exploring historic Old Town Key West, filled with colourful houses, bars and restaurants that will immerse you in the authentic culture and history of the island. Undoubtedly one of the best Key West tours to experience the charm of the illuminated city.

Book a bike tour

10. Watch dolphins on a dolphin watching experience

Dolphin Watching| ©jarkmarvis
Dolphin Watching| ©jarkmarvis

Would you like to see dolphins in their natural habitat? In Key West you can sign up for this activity at sunset when you book your dolphin watching tour. The activity is one of the top things to do in Key West with kids, although let's be honest, adults and children enjoy it equally.

To see the dolphins you'll be taken on a catamaran (sometimes with a glass bottom) to make your way across the gulf to the Key West Wildlife Refuge, the area's wildlife and dolphin sanctuary. You'll see playful Atlantic bottlenose dolphins leaping out of the water and frolicking around the boat.

One of the highlights of this archipelago is that dolphin watching is an eco-friendly activity. Following the "Dolphin SMART", the law of protection for these mammals, all operators are obliged to follow certain rules to avoid the impact on the marine fauna.

Book the dolphin spotting tour

11. Relax on the beach

Key West Beach| ©Olli Ronimus
Key West Beach| ©Olli Ronimus

One of the keys to understanding the small paradise of Key West is to understand that this island is a paradise even at night. Its beaches offer visitors the opportunity to relax and enjoy the natural beauty of the area. In addition, many of these beaches are open until well after sunset, offering a unique opportunity to relax in the evening.

If you feel like strolling along the beach after dark, you're in luck: most of the beaches in Key West officially close around 23:00, which means you can enjoy the sand, sea and stars long after the sun goes down.

While some people may think of a walk on the beach as a romantic activity, it's also a great way to relax and de-stress after a long day of sightseeing or adventure. Whether you're looking for a solitary or romantic experience, an evening stroll along the beach is a great way to enjoy the natural beauty of Key West with one of its 9 must-see attractions.