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Destinations  •  October 03, 2022

31 Best Things to Do in Key West

Peter Lane Taylor
Peter Lane Taylor

After spending two decades on five continents, Peter has a natural knack for travel writing. He's a regular contributor to Forbes and formerly worked as a contract expedition writer, photographer, and filmmaker for National Geographic Adventure. Currently, Peter is in development on the real estate television drama series "Everglades" and writing the exclusive memoir on Hollywood's top stuntman.

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Key West enjoys a privileged vacation in southwest Florida, claiming the title of the southernmost city in the continental United States. Although Key West is a mere four miles long and 1.5 miles wide, this tourist attraction packs a punch with activities to do.

Did you know that Key West is that it’s closer to Cuba than it is to Miami? Cuba is only 95 miles away at its nearest point, whereas Miami is 130 miles by flight, offering bragging rights when you return from your vacation or choose to call Key West home.

Before the 19th century, the Native American tribes Calusa and Tequesta lived in Key West. Once the Spanish transferred Florida from Spain to Great Britain in 1763, they moved these natives to Cuba. It wasn’t until 1822 when Lieutenant Commander Matthew C. Perry set a U.S. flag in the Florida Keys and declared it American territory.

Since then, Americans and foreigners alike have flocked to experience the historical and nature-based things to do in Key West. Some people even love it so much that they decide to make Key West their permanent home base. Regardless of your situation, we’ll share the must-dos in Key West. So, get ready and take notes of the best Key West attractions.

1. Make a Bee-line to Duval Street

Duval Street is the place to see in Key West if you’re short on time. The approximately one-mile street sits in the heart of Key West’s old town, between the Gulf of Mexico and the Atlantic Ocean.

Many of the activities we’ll be discussing here call Duval Street home, as it boasts many famous Key West restaurants, attractions, and shops. You can expect crowds day and night along Duval Street, and the nightlife there is outstanding. Live music and street performers make the experience even more special. 

2. Meander Around Mallory Square

Mallory Square is an iconic place in Key West, which sits south of Duval Street. The ample space sits on a historic waterfront area of Key West, and you’ll find countless dining and shopping options equipped with souvenirs. 

Watching the sunset at Mallory Square is a must when you’re in Key West. Just be prepared to share the view with hundreds of others vying for a good viewpoint.  Once the sun goes down, Mallory Square comes to life with free live street performances called the Sunset Celebration, some of which have adult content.

3. Explore Fort Zachary Taylor Historic State Park

Fort Zachary Taylor is a state park that predates the Civil War. It’s a budget-friendly thing to do in Key West, given that you pay per vehicle instead of per person. History lovers will appreciate the brick paths that lead you through cannons and gun ports. You can hire a tour guide for more historical context.

Fort Zachary also offers a wonderful respite for relaxing on the beach, swimming in crystal clear water, snorkeling, and several other water sports.

4. Walk Through Dry Tortugas National Park

Dry Tortugas National Park is anything but dry—the only way to arrive at this 100-square-mile park is via boat or seaplane. The park comprises seven islands and is world-renown for the picturesque Fort Jefferson, a former prison during the civil war. 

During your day trip to Dry Tortugas, you can take a guided tour of Fort Jefferson, walk pristine beaches, snorkel with colorful fish, and relax in the sun.

5. Stand at America’s Southernmost Point

No trip to Key West is complete without visiting the Southernmost Point, a buoy on the shore that represents the southernmost part of the continental United States. The buoy sits at the end of Old Town Key West surrounded by historic homes and architecture as well as several of Key West’s best restaurants and bars. If you’re hoping to snap a photo of yourself next to the buoy without eating into too much of your day, definitely plan on arriving there at dawn since it gets really crowded at sunset.

A common misconception of non-locals is that you can see Cuba from the Southernmost Point. Unfortunately, you’d need a really big set of binoculars to do that since it’s impossible to see farther than 16 miles on the water anywhere in the world due to the curvature of the earth.

6. Visit the Ernest Hemingway Home and Museum

Ernest Hemingway is arguably Key West’s most famous resident and the museum that was once his home is one of Key West’s most popular places to visit. You also may not think of visiting a museum to see real-life six-toed cats, but it’s a great way to coax the non-history buff to go here. Legend has it that Hemingway received a six-toed cat from a captain of a ship, and today many of this cat’s six-toed descendants still wander the museum’s property.

Aside from cats, what makes the Ernest Hemingway Home and Museum a must-visit is that you’ll get to explore the actual place where one of America’s greatest authors wrote 70% of his work.

7. Snorkel With Tropical Fish

Whether you bring your own gear or rent from one of the many dive and snorkel shops on the island, Key West is one of the best and only places in the continental U.S. to discover coral reefs and see colorful tropical fish. Some of the best locations to do so include:

  • Fort Zachary Taylor State Park Beach
  • Higgs Beach

You can also sign up for a boat tour that will take you to snorkeling spots away from mainland Key West and in particular out to the coral barrier reef 7-miles offshore which is the third longest in the world. If you love the water and have never been to the tropics before, take at least one snorkel boat trip since the reefs are in better shape offshore because they receive less human traffic.

8. Dive To See the Vandenberg

The Vandenberg is a scuttled former U.S. Navy ship that scientists intentionally sunk in 2009 to purposefully help to create an artificial coral reef to give fish and other marine life a place to thrive and new coral the opportunity to grow.

Nowadays, it’s a favorite spot for both experienced and novice scuba divers, as there are approximately ten stories of ship structure to explore. At its greatest depth, the Vandenberg sits 150 feet underwater off the coast of Key West and is considered one of the best wreck dives in the Florida Keys.

9. Tour the Harry S. Truman Little White House

The Harry S. Truman Little White House was the winter haven for former President Truman. Formerly, the house was part of the Key West Naval Station. But when Truman fell ill in 1946, his doctor prescribed him a warm vacation getaway.

He loved his time there so much that he started visiting more frequently, realizing that he could turn any place into the White House as long as he worked there. Nowadays, you can take a guided tour through Truman’s former home.

10. Take a Sunset Cruise

One of the most iconic things to do in Key West is to take a sunset cruise tour since there are 360-degree views of the sunset from almost everywhere on the water. There’s no shortage of tour agencies ready to book your trip, and you can choose from various sunset cruises, boat styles, and lengths of time to suit people of all ages, budgets, and interests. 

Private charters, dinner cruises, and dolphin tours combined with watching the sunset are some of the many choices you’ll have. We encourage you to shop around to land the best price. And if you’re looking for an extra special trip, hiring an event planner is an excellent option.

11. Spend Time at the Key West Aquarium

The Key West Aquarium is one of the best things to do in Key West for families. Here you’ll learn about the hundreds of marine species native to the Key West area, the coral barrier reef, as well as marine conservation efforts to conserve it. When it opened its doors in 1935, the aquarium cost 15 cents for an adult ticket. Although you can’t snag such a deal there these days, the touch tank and educational programs make it well worth the visit especially for young kids.

Some of the species you’ll encounter at the Key West Aquarium include sharks, stingrays, and dozens of different tropical fish. They even have animals such as iguanas and an American Alligator.

12. Kayak Through Mangroves

Mangroves play a vital role in Key West’s ecosystem, given that they offer shelter and food for marine and non-marine animals alike. They also help prevent coastal erosion. 

By visiting Key West, you can enjoy exploring the mangroves in an eco-friendly way by renting kayaks. Because the mangroves protect from wind and waves, you can expect a peaceful experience as you watch crabs climbing on the roots, fish swimming beside you, and birds flying overhead.

13. Admire the Audubon House and Tropical Gardens

Visiting the Audubon House and Tropical Gardens is a fantastic option if you want to travel back in time during your stay in Key West. You’ll get to wander through the rooms of this 1840s house, which was home to one of Key West’s most famous mariners, Captain John Huling Geiger.

You’ll feel the luxury the moment you step inside Geiger’s home since like many of Key West’s historic captains he earned a fortune from the shipwrecking industry. The tropical gardens are equally as jaw-dropping as the architecture, making you feel that you’re in a Caribbean oasis surrounded by orchids, palms, crotons, and colorful birds and butterflies.

14. Hop on a Bike

There are limited parking spots on Key West, and the fees are expensive, which makes exploring the island by bike an excellent option. Due to the island’s small size, a person of average fitness level can easily explore the entire island by bike.

You’ll encounter many racks around the town where you can store your bike—just be sure your bike rental company gives you a lock. If you’re traveling during the summer, bring lots of water, for the sun is strong.

15. Go on a Dolphin-watching Excursion

We’ll lead with this—seeing dolphins from the shore when walking along Key West’s coast is possible. But if you want a chance to see them closer, taking a dolphin boat tour is an excellent choice.

Atlantic Bottlenose Dolphins are the most popular type of dolphin in Key West. Although no tour company can guarantee wild dolphin sightings, these mammals are accustomed to tourists, so it’s common for them to approach boats.

16. Observe Butterflies at the Key West Butterfly and Nature Conservatory

The family-friendly Butterfly and Nature Conservatory is an exciting way to get up close to butterflies, many of which are native to Key West and the Florida Keys. If you get lucky, one of the hundreds of butterflies at the conservatory also might just land on you!

You’ll also get to admire tropical birds, including two flamingos. And don’t miss the opportunity to take home a real butterfly souvenir. If you drive, the left side of the building behind the garden has free parking.

17. Explore a Warship at the Cutter Ingham Maritime Museum

Visitors to Key West fascinated by maritime history will have an opportunity to geek out on the past by visiting the U.S. Coast Guard Cutter Ingham. The Ingham is the only ship today still afloat that’s received two U.S. Presidential Unit Citations for heroism.

You can tour the Ingham by heading to the Truman Waterfront near Truman’s winter White House. If you have young children that aren’t interested in visiting the ship, they can play at a multi-million dollar playground equipped with water slides.

18. Give Your Feet a Break on the Key West Trolley

Even though Key West is small, you can easily rack up 10,000 steps and more by crisscrossing the island as you visit all of the amazing places to see and visit. So buying a one or two-day pass on one of Key West’s hop-on-hop-off trolleys is one of the best things to do in the Conch Republic to spare your feet and save some time.

The trolley makes 13 stops at Key West’s most notable points of interest. You can get off at each stop or spend the day cruising around the trolley sightseeing. Best of all, the trolley has frequent departures, so you don’t have to crimp your sightseeing schedule around theirs.

19. Learn About the Florida Keys at the Eco-discovery Center

Depending on what you choose to do, a visit to Key West can do a number on your bank account, but it doesn’t have to. The Eco-Discovery Center is an excellent example of this. It’s an admission-free 6,000-square-foot facility that offers an in-depth way to learn about the plants and animals native to the Florida Keys and is great for both kids and adults. 

During your visit to the Eco-Discovery Center, you can learn about coral reefs, shipwrecks, marine life, plants, endangered species, and the tracking tools scientists use to monitor the ocean’s health, and more. You can also observe live fish and other marine life in a 2,500-gallon reef tank and experience a mock version of Aquarius, the only underwater ocean laboratory in the world.

20. Gawk at the Buildings at Key West Bight Marina

Key West Bight is a place to wander the marina as your head swivels between admiring the architecture of old homes and looking at flashy modern boats docked at the port. It’s a place for tourists and locals alike to enjoy an afternoon stroll or a fine dining experience at one of the many restaurants.

Visiting the Key West Bight Marina is also an excellent place to go shopping or book the tour you’ve been meaning to arrange. It’s a bustling area and has been that way for almost 200 years, as the marina has been a central place for Key West’s economic survival. 

21. Climb the Key West Lighthouse

The Key West Lighthouse formerly belonged to the U.S. Navy. Nowadays, visitors can climb up its 88-step staircase for stunning views over the Atlantic Ocean, the Gulf of Mexico, downtown Key West, and the rest of the Lower Florida Keys.

The Key West Lighthouse is open seven days a week. But don’t expect to climb to the top at sunset since the last admission is at 4:30 pm. You can also book discounted tickets online which will save you a little bit of money.

22. Partake in Water Sports

It should come as no surprise that visiting an island like Key West surrounded by the ocean offers the opportunity to experience water sports until you can’t take it anymore. In addition to booking a sunset boat tour or snorkeling or diving excursion, you can get your adrenaline pumping with dozens of other water sports including:

  • Jet skiing
  • Parasailing
  • Kite boarding
  • Wind surfing
  • Banana boat rides
  • Glass bottom boats

You can also rent a boat and spend a day on the water exploring Key West at your leisure on your own. Since there’s so much competition among water sports tour providers, you can often negotiate a good deal, especially if you want to book more than one tour. Or let our AvantStay Concierge team handle the trip planning for you once you book one of our Key West homes!

23. Beach Yourself at Lagerheads

Lagerheads Beach is one of the best (and only) strips of sandy beach in Key West and Lagerheads Beach Bar is one of the best places on the island to find an excellent selection of food, drinks, snorkel gear, and more for a day of fun in the sun.

It’s common to encounter locals kicking back here with a drink under one of Lagerheads’ many shaded tables and chatting about island life. Best of all, since Lagerheads isn’t in the center of Key West’s most touristy attractions, it has relatively fewer crowds and it’s easier to get in.

24. Escape the Rain at Tropic Cinema

Rain keeps Key West the lush and tropical island oasis that visitors and locals love, so you should have some indoor backups during your time here. Tropic Cinema is an excellent option, as it’s an independent cinema that features a combination of Hollywood blockbusters as well as international indy films.

There’s no mistaking this cinema for the cineplex-style movie theater you’ve been to in the past; it has an Art Deco marquee flair. You’ll also encounter a Marilyn Monroe sculpture and Key West’s version of the Hollywood Walk of Fame. Don’t miss out on the chance to purchase popcorn at Tropic Cinema, which is famous on the island.

25. See Artifacts at the Shipwreck Treasure Museum

Key West is legendary for pirates, shipwrecks, and underwater treasure hunters so the Shipwreck Treasure Museum is a fun way to get your kids interested in maritime history and the ocean. In addition to exploring the museum with real artifacts collected from shipwrecks, you can climb up to the Captain’s Observatory and see how captains used to spot cargo ships.

The museum does an excellent job of narrating thrilling true stories about the mariners who risked their lives to collect treasure buried at the bottom of the ocean around Key West before advanced, modern scuba diving and underwater sonar equipment existed.

26. Partake in the Party at Fantasy Fest

If you’re looking for some adult fun, Fantasy Fest is a classic Key West festival that occurs for ten days every October. It was started in 1979 by “Conchs” (locals born in Key West) and is now one of the most anticipated annual events on the island. It’s also an excellent opportunity for locals to rent out their homes through a vacation rental management company.

Fantasy Fest is a bit like a week-long Halloween party for adults. People dress up in elaborate costumes and makeup, partaking in parades and parties that seem to run 24/7. One of the biggest highlights during Fantasy Fest is the Bud Light Fantasy Fest Parade, which gives Superbowl ads a run for their money. 

27. Learn About Cuban History at the San Carlos Institute

The San Carlos Institute is a looker from the outside with its tasteful architecture, and inside it holds a trove of Conch Republic history. Started in 1871 by Cubans exiled in Key West, it was once one of the foundations of Cuba’s independence movement.

Visitors to the San Carlos Institute can browse through a museum, art gallery, and library and there’s also a theater and school. The San Carlos Institute is an excellent place for people wanting to have a deeper understanding of Cuban history as it relates to Key West and the close connection between the two islands.

28. Visit the Oldest Eatery in the Florida Keys

Pepe’s Cafe is Key West’s local secret that’s no longer a secret. The restaurant opened its doors in 1909, making it the oldest restaurant operating in the Florida Keys. It’s hard not to fall in love with Pepe’s as you dine outside in an environment that will take you back in time to old Florida life.

One of the best things to do in Key West when your feet are tired from exploring is to eat—and Pepe is one of the best and most historic places on the island to do this. They bake their own bread, shuck their oysters in-house, and all of their salad dressings are handmade. 

29. Learn About Sea Turtles at the Turtle Museum

The Turtle Museum is a small but charming opportunity for kids and adults to learn about the endangered sea turtles that are native to the Florida Keys. There’s no entrance fee to visit and you’ll learn the fascinating background of how sea turtles lay eggs, migrate, and survive in the ocean environment, as well as see some actual sea turtle bones up close. 

The Turtle Museum also offers kid-friendly activities to keep younger visitors engaged. By the time you leave the Turtle Museum, you’ll be ready to protect these majestic sea creatures that have become so vulnerable in the Florida Keys and elsewhere around the globe.

30. Grab a Drink at Sloppy Joes

If you only have one chance to visit a taproom in Key West, make it Sloppy Joes. The beloved bar on Duval Street established itself on the day that the U.S. government repealed prohibition. At the time, it was a speakeasy. Now, it’s a favorite spot for tourists and locals to get their fill of alcohol.

And, yes, you can buy an infamous sloppy joe sandwich from Sloppy Joes. The no-frill ingredients of ground beef, tomato sauce, onions, and peppers might sound simple, but it’s the go-to order for many people visiting this bar. If sloppy joes aren’t your thing, Sloppy Joes offers an extensive menu of other food, including their famous key lime pie.

31. Go Back in Time to the Oldest House Museum

There’s no trick to this place’s name; the Oldest House Museum is the oldest house in Key West and claims the title of the oldest house in South Florida, built in 1829. 

Some people prefer to admire the Oldest House Museum from the outside, as you’ll pass it walking down Duval Street. But if you love history, you’ll want to give this museum a tour. It contains the oldest Cook House remaining in South Florida and tells the amazing story of the many generations of people who have occupied the home over the years.

Conclusion

We’re confident you’ll have a fantastic vacation since there are so many fun things to do in Key West. However, as some departing advice, note that only one road leads to Key West from the continental U.S.

So, if you drive there, pack some snacks and a flexible mindset in case an accident on the road delays your arrival. We guarantee the activities in Key West will make it worth the wait.

Peter Lane Taylor
Peter Lane Taylor

After spending two decades on five continents, Peter has a natural knack for travel writing. He's a regular contributor to Forbes and formerly worked as a contract expedition writer, photographer, and filmmaker for National Geographic Adventure. Currently, Peter is in development on the real estate television drama series "Everglades" and writing the exclusive memoir on Hollywood's top stuntman.

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