Top 20 Fun and Unusual Things to Do in Key West: A Guide for Adventure-Seeking Travelers to the Florida Keys!

If you’re an adventure-seeking traveler looking for exciting and unique things to do in Key West, then you’ve come to the right place. The Florida Keys are a popular destination for vacationers from all over the world, and Key West is the crown jewel of this tropical paradise.

In this guide, we’ll take you on a journey through the most exciting and unusual activities that Key West has to offer. From haunted ghost tours to festivals and museums, you’ll find plenty of ideas to make your vacation unforgettable.

Whether you’re traveling with family, friends, or on your own, our guide will help you plan the perfect itinerary to experience all that Key West has to offer. So grab your sunscreen, put on your flip-flops, and get ready for a fun-filled adventure in the sunshine state!

1. Experience the Wacky Fun of the Annual Conch Republic Bed Race in Key West

One of the most unique and exciting events in Key West is the annual Conch Republic Bed Race. Every year, participants gather to race their homemade beds down the streets of the island. It’s a high-energy event that draws crowds of spectators, all cheering for their favorite team.

The race is not just about speed – the beds are also judged on creativity and design, making it a true test of both speed and creativity. Teams spend weeks designing and building their beds, incorporating everything from flashy colors to intricate themes.

But the fun doesn’t stop there. Along the race route, there are also various pit stops and challenges, adding an extra level of excitement to the event. It’s a truly unique experience that you won’t find anywhere else, and it’s a great way to get involved in the community and make new friends.

So if you’re looking for a one-of-a-kind experience in Key West, make sure to check out the annual “Bed Race” and join in on the fun.

2. Explore the Haunted History of Captain Tony’s Saloon, with a Bar Made from an Old Boat, in Key West

If you’re looking for a spooky spot in Key West, you can’t go wrong with a visit to Captain Tony’s Saloon. This iconic bar has been around since the 1850s and boasts a fascinating history that includes serving as a morgue, a brothel, and even the headquarters for a prominent American businessman. Today, the saloon is a popular spot for tourists and locals alike, drawn by its unique decor and rumored hauntings.

One of the most unusual features of Captain Tony’s Saloon is the bar itself, which is made from a boat. As you sip your drink, take a moment to appreciate the intricate details of the vessel, including its brass fittings and intricate woodwork.

If you’re brave enough, be sure to ask the bartenders about the ghostly sightings that have been reported over the years. Many visitors have claimed to see the ghost of a former patron who met a grisly end in the bar. Regardless of whether you believe in the paranormal, a visit to Captain Tony’s Saloon is an unforgettable experience.

3. Get Your Costume Ready for Key West’s Wildest Party: Fantasy Fest!

If you’re looking for a unique and unforgettable experience in Key West, you won’t want to miss the annual Fantasy Fest in October. This week-long event is known for its outrageous costumes, wild parties, and lively atmosphere.

During the festival, the streets of Key West come alive with parades, street parties, and live music. People from all over the world come to participate in the festivities, dressing up in elaborate costumes and taking part in events like the masquerade march, pet masquerade, and body painting contests.

The highlight of the festival is the grand parade, where colorful floats and marching bands make their way through the streets, creating a dazzling spectacle. Whether you choose to watch from the sidelines or join in the fun by dressing up in your own costume, Fantasy Fest is sure to be an experience you’ll never forget.

So, mark your calendar for October and get ready to let your hair down, and embrace your wild side at Fantasy Fest in Key West!

4. Flutter with Delight: Visit the Key West Butterfly and Nature Conservatory

The Key West Butterfly and Nature Conservatory is a must-visit attraction for anyone looking to experience the beauty of nature up close. This unique conservatory is home to hundreds of butterflies, which flutter and float around in a lush tropical setting. As you stroll through the conservatory, you’ll see a variety of exotic species, including the striking blue morpho and the delicate swallowtail butterfly.

The conservatory is designed to mimic the natural habitats of these beautiful creatures, with plenty of flowers, plants, and trees to provide food and shelter. You can also learn about the life cycle of butterflies and see their eggs, caterpillars, and cocoons up close.

The conservatory is a peaceful and relaxing spot, and it’s a great place to take a break from the hustle and bustle of Key West. You’ll leave feeling refreshed and inspired by the beauty of nature. Whether you’re a nature lover or just looking for a unique and tranquil experience, the Key West Butterfly and Nature Conservatory is definitely worth a visit.

5. Channel Your Inner Hemingway: Compete in the Look-Alike Contest at Sloppy Joe’s Bar!

If you’re a fan of Ernest Hemingway’s writing or just looking for a unique experience in Key West, don’t miss the annual Hemingway Look-Alike Contest at Sloppy Joe’s Bar. Held each year in July, this lively event draws in hundreds of contestants from around the world who resemble the iconic author with their beards, mustaches, and distinguished style.

The contest celebrates the legacy of Hemingway, who lived and wrote in Key West during the 1930s. In addition to the contest, visitors can explore the memorabilia on display at the bar, including photos, letters, and the author’s favorite stool. Plus, enjoy a refreshing drink and mingle with other Hemingway enthusiasts.

Whether you’re participating in the contest or just watching from the sidelines, the Hemingway Look-Alike Contest at Sloppy Joe’s Bar is a fun and memorable experience that you won’t soon forget. So grab a mojito and soak up the literary atmosphere at this historic Key West landmark.

6. Unleash Your Inner Ghostbuster: Join the Key West Ghost Hunt Tour for a Spooky Adventure!

If you’re a fan of spooky thrills and chills, then the Key West Ghost Hunt tour is an activity that you simply cannot miss. This one-of-a-kind tour takes you on a journey through some of the most haunted locations in Key West, where you’ll learn about the history and folklore of the island’s most notorious spirits.

During the tour, you’ll be equipped with paranormal investigation tools and led by experienced guides who will take you to the most active locations for ghost hunting. You’ll explore creepy cemeteries, old hotels, and abandoned buildings, all while learning about the spooky legends and mysterious happenings that have made these locations infamous.

Whether you’re a true believer in the paranormal or just looking for a unique and thrilling way to experience Key West, the Key West Ghost Hunt tour is an adventure that you won’t soon forget. So grab your flashlight, muster up some courage, and get ready for a spine-tingling journey into the unknown.

7. Mallory Square Magic: Join the Sunset Celebration and Witness the Best Street Performers in Key West!

The nightly Key West Sunset Celebration at Mallory Square is a beloved tradition among locals and visitors alike. Every evening, crowds gather at this historic waterfront square to watch the sunset over the Gulf of Mexico.

The celebration features street performers, food vendors, and local artisans selling their wares. Musicians, jugglers, and magicians entertain the crowds with their acts, while food vendors offer everything from fresh seafood to classic carnival fare.

As the sun begins to set, everyone turns their attention to the horizon, eagerly awaiting the moment when the sun dips below the water. The sky lights up in a spectacular display of oranges, pinks, and purples, and the sound of applause echoes across the square.

The nightly Sunset Celebration at Mallory Square is a true testament to the laid-back, fun-loving spirit of Key West. Whether you’re looking for a romantic evening or a lively night out with friends, this is one experience that you won’t want to miss.

8. Grave Expectations: Uncovering the Unusual and Creepy Key West Cemetery

Key West is known for its quirky and offbeat attractions, and the Key West Cemetery is no exception. This historic cemetery, located on Solares Hill, is the final resting place of some of the island’s most notable residents, including famous cigar makers, sailors, and wreckers. However, what makes this cemetery unique are the unusual and sometimes creepy gravestones and epitaphs that can be found throughout the grounds.

Visitors can take a self-guided tour of the cemetery and discover some of its more unusual features, such as the grave of a young girl who is said to have been buried alive and the “personality headstones” that reflect the character of the person buried there. The cemetery also has a section dedicated to victims of the 1898 Spanish-American War and a memorial to the victims of the USS Maine.

If you’re looking for a spooky and intriguing activity to do in Key West, a visit to the historic Key West cemetery should definitely be on your list.

9. Sail Away on the Jolly II Rover Schooner in Key West, Florida!

If you’re looking for a unique and memorable way to experience the beauty of Key West, a boat ride on the Jolly II Rover schooner is a must-try activity. This classic vessel is a replica of a 19th-century sailing ship, and it’s sure to transport you back in time while you explore the crystal-clear waters surrounding the island.

During your boat ride, you’ll have the chance to take in stunning views of the Key West coastline and the turquoise waters of the Gulf of Mexico. You can relax on the deck, soak up the sun, and even help the crew hoist the sails if you’re feeling adventurous.

Whether you’re traveling solo or with a group, a boat ride on the Jolly II Rover is an excellent way to create lasting memories and experience the best of Key West. So why not climb aboard and set sail for an unforgettable adventure on the high seas? Ahoy, mateys!

10. A Presidential Stay: Visit the Little White House in Key West

Visiting the Little White House is a must-do for history buffs and anyone interested in Presidential history. President Harry S. Truman used to stay here when visiting Key West, and the house has been preserved to give visitors a glimpse into Truman’s life while he was in office.

The house is filled with artifacts, including Truman’s desk and other personal items. Visitors can take a guided tour to learn more about the history of the house and the important decisions that were made there. The house also features beautiful gardens that are worth exploring.

In addition to the historical significance of the house, there are also special events held there throughout the year. From wine tastings to holiday events, the Little White House is a unique venue that offers a glimpse into the past while also providing plenty of entertainment for modern-day visitors.

Located in the heart of Old Town Key West, the Little White House is easily accessible and is just one of many unusual things to do in the Florida Keys. Whether you’re a history lover or just looking for a fun way to spend an afternoon, the Little White House is a must-visit destination.

11. Fun with Moving Art: Attend the Papio Kinetic Sculpture Parade!

The Papio Kinetic Sculpture Parade is a unique and creative event that takes place annually in Key West. This parade showcases dozens of handmade kinetic sculptures that move and spin in different directions, propelled by human power. It’s an exciting and fun event that is perfect for families and anyone who loves art and creativity.

The parade route winds through the historic Old Town area, with spectators lining the streets to cheer on the colorful and whimsical sculptures. The artists and creators of these sculptures put in hours of work and ingenuity to make them come to life, and the result is a delightful display of art and imagination.

If you’re looking for something truly unusual and unforgettable to do in the Florida Keys, attending the Papio Kinetic Sculpture Parade is a must. You’ll be amazed by the creativity and ingenuity of the sculptures, and it’s a great way to spend a fun day outdoors in beautiful Key West.

12. Hop on the Trolley of Terror: A Ghostly Adventure in Key West

The Ghost and Gravestone trolley tour is a must-try activity for thrill-seekers looking for a spine-tingling adventure. This tour takes you to some of the most haunted locations in Key West, where you can listen to ghost stories and learn about the island’s darker history. The trolley itself is a sight to behold, with its gothic-style architecture and ominous interior lighting setting the tone for the tour.

The tour guides are knowledgeable and passionate about Key West’s ghostly past, and they use special effects to enhance the eerie atmosphere. You’ll visit spooky cemeteries, haunted mansions, and other locations where the paranormal is said to be active. Whether you believe in ghosts or not, this tour is sure to give you goosebumps and leave you with a newfound appreciation for Key West’s supernatural side.

Don’t miss the opportunity to experience the Ghost and Gravestone trolley tour, a unique and unforgettable way to explore the island’s haunted history.

13. Uncover the Secrets of Key West’s Maritime History at the Shipwreck Treasure Museum

The Key West Shipwreck Treasure Museum is an enthralling attraction that offers a fascinating glimpse into the world of shipwrecks and treasure hunting. Situated in the heart of Old Town, this museum is a must-visit for anyone intrigued by maritime history.

At the museum, you can witness artifacts retrieved from shipwrecks, view live demonstrations of how treasures were salvaged from the ocean floor, and even ascend to the top of a 65-foot lookout tower for a breathtaking panoramic view of the island.

One of the highlights of the museum is the interactive exhibits that enable you to experience what it was like to be a crew member on a 19th-century wrecking vessel. You can also discover the intriguing characters who were involved in the shipwrecking industry and the battles that were fought over the treasure that was recovered.

Whether you’re an adventurer at heart or just looking for a unique experience in Key West, the Shipwreck Treasure Museum is a must-visit attraction. So, grab your map and compass and set sail for excitement at this thrilling museum.

14. Meet Robert the Haunted Doll: A Spooky Adventure in Key West!

Robert the Doll is a popular and creepy attraction in Key West, Florida. The doll is said to be possessed by an evil spirit and has been the subject of many eerie tales. Legend has it that the doll belonged to a young boy named Robert Eugene Otto, who claimed that the doll moved and talked to him. After his death, strange occurrences continued to happen in the house, leading many to believe that Robert’s spirit had become attached to the doll.

Today, visitors can visit the doll at the Fort East Martello Museum in Key West. Robert is housed in a glass case, dressed in his sailor suit and clutching his stuffed lion. Visitors are warned to be respectful and not to take photos of the doll without asking for his permission. Many people believe that bad luck will follow anyone who disrespects the doll.

If you’re looking for a spooky and unusual thing to do in Key West, visiting Robert the Doll should definitely be on your list. But beware, as some visitors have reported feeling uneasy or even experiencing strange occurrences after encountering the creepy doll.

15. Shine a Light on Key West’s Past: Visit the Key West Lighthouse and Keeper’s Quarters Museum

Whether you’re a curious traveler or an adventurous explorer, the Key West Lighthouse and Keeper’s Quarters Museum is a must-visit attraction. Located in the heart of Old Town, this museum offers a unique opportunity to learn about the history of the lighthouse and climb to the top for a breathtaking view of the island.

At the museum, you can explore exhibits showcasing the daily lives of lighthouse keepers and their families, including historic photographs and artifacts. The keeper’s quarters have been restored to their original 19th-century appearance, providing an immersive experience of what life was like for these keepers.

But the highlight of the museum is undoubtedly the climb up the lighthouse tower. With 88 steps to the top, the view from the lighthouse is simply spectacular. From this vantage point, you can see the beautiful blue waters and colorful buildings that make Key West such a unique and vibrant destination.

So, whether you’re interested in history, architecture or just seeking a stunning view, the Key West Lighthouse and Keeper’s Quarters Museum is a must-visit attraction that should not be missed.

16. Tasting Paradise: Key West’s Best Food and Drink Festival

Taste of Key West is an annual food and drink festival that attracts visitors from all over the world. Held in early April, this event features some of the best culinary delights that Key West has to offer.

At Taste of Key West, you can sample a variety of local dishes, ranging from fresh seafood to spicy conch fritters. You can also indulge in tropical cocktails and craft beers while enjoying live music and entertainment.

This event takes place at the Truman Waterfront Park Amphitheater, which is located on the waterfront in Old Town. It’s the perfect place to spend a beautiful afternoon or evening with friends and family, enjoying delicious food and drinks while taking in the stunning views of the ocean.

If you’re a foodie or just looking for a fun way to experience Key West’s unique cuisine, the Taste of Key West event is not to be missed. So, mark your calendar and come hungry for an unforgettable culinary experience.

17. Unlock the Secrets of Key West’s Past and Present at the Art and Historical Society!

The Key West Art and Historical Society is a must-visit for anyone interested in the island’s rich history and vibrant arts scene. Located in the historic district of Old Town, this museum is home to a collection of exhibits and galleries that showcase the works of local artists and the island’s unique cultural heritage.

One of the highlights of the museum is the “Overseas to the Keys” exhibit, which explores the history of the construction of the Overseas Highway and the impact it had on the development of Key West. You can also see a collection of impressive art and artifacts, including paintings, sculptures, and historic objects.

In addition to the permanent exhibits, the museum also hosts rotating temporary exhibits, special events, and educational programs throughout the year. Whether you’re a history buff or an art lover, the Key West Art and Historical Society has something for everyone.

So, if you’re looking for unique things to do in Key West, make sure to add this museum to your list. You won’t want to miss the opportunity to explore the island’s rich cultural heritage and vibrant arts scene.

18. Get Your Zombie On: Join the Undead at Key West’s Zombie Bike Ride

Are you ready for a spook-tacular experience? Join the annual Zombie Bike Ride in Key West, where participants dress up in zombie costumes and ride their bikes through the streets of the island. This unique event is free and open to the public, making it a perfect option for those looking for fun and unusual things to do in Key West.

The Zombie Bike Ride is a festive and interactive event that celebrates Halloween in a unique way. Participants can get creative with their zombie costumes and decorate their bikes with spooky accessories. The ride usually starts at the East Martello Tower and Museum, where participants gather for a pre-ride party.

The bike ride itself is a fun and surreal experience as zombies of all ages and backgrounds pedal through the island’s streets, groaning and moaning. The route usually takes the riders along the beautiful waterfront and past some of Key West’s historic landmarks.

So, dust off your old bike, grab your zombie makeup, and join the fun at the next Zombie Bike Ride. It’s a one-of-a-kind experience that you won’t forget.

19. Explore the Wonders of Nature: A Visit to Florida Keys Eco-Discovery Center

The Florida Keys Eco-Discovery Center is a fantastic destination for anyone interested in learning more about the local environment and marine life. Located in Key West, the center offers visitors an interactive and educational experience that is perfect for families and individuals alike.

At the center, you can explore interactive exhibits that showcase the unique ecosystems of the Florida Keys, including coral reefs, mangrove forests, and seagrass beds. You can also learn about the native plants and animals that call these habitats home, as well as the challenges facing these delicate ecosystems and what we can do to help protect them.

One of the highlights of the center is the 2,500-gallon reef tank that allows you to see a variety of marine life up close, including colorful fish, lobsters, and sea turtles. You can also participate in a range of educational programs, such as guided tours and hands-on activities for kids.

Whether you’re a nature enthusiast or just looking for an engaging and informative experience in Key West, the Florida Keys Eco-Discovery Center is a must-visit attraction. So, explore the wonders of the local environment and discover the importance of conservation efforts at this fantastic center.

20. Discover Key West’s Architecture: Take a Conch Tour of Historic Buildings

The Conch Tour Train is a popular attraction in Key West that takes visitors on a journey through the island’s rich history and unique architecture. This charming tour is a must-do for anyone interested in learning about the island’s past and seeing some of its most beautiful buildings and homes.

The tour starts in the heart of Old Town and takes you on a 90-minute journey through the island’s charming streets, past historic landmarks, and stunning mansions. The guide provides an interesting commentary on the island’s history, culture, and architecture, making the tour both educational and entertaining.

One of the highlights of the tour is the opportunity to see the island’s famous conch-style architecture up close. The unique design is characterized by wooden structures with high-pitched metal roofs, which helped keep homes cool in the island’s hot climate.

Whether you’re a history buff or just looking for a fun way to explore the island, the Conch Tour Train is a great option. So, hop aboard and discover the unique architecture and charm of Key West.

After exploring all the fun and unusual things to do in Key West, we hope you’re as excited to visit this unique island as we are! From haunted tours to eco-discovery centers, there’s truly something for everyone to enjoy.

But we want to know – which activity are you most looking forward to trying on your trip to Key West? Are you a history buff excited to visit the Shipwreck Treasure Museum, or are you more intrigued by the idea of a zombie bike ride? Maybe you’re excited to taste the local cuisine at the Taste of Key West event or explore the island’s unique architecture on a Conch Tour.

Whatever it is, we want to hear from you! Leave a comment below and let us know which of these activities you’re most excited to try or if there’s another Key West attraction that we missed. Happy travels!

Featured photo: gustavofrazao via Canva.com