27 of the Best Things to Do in Key West, Florida

Written By: The Planet D

This comprehensive guide to the best things to do in Key West, Florida will take you through the traditional sites like Mallory Square and Duval Street but we also share some of the more unique attractions in Key West like a tour of the coast and marina on hydro bikes.

Key West will transport you to the islands. You may still be in Florida but it feels more like vacationing in the Caribbean. It makes sense considering the Key West is closer to Havana than Miami. The southernmost point of the United States is located here and it is only 90 miles from Cuba!

Best Things to do in Key West

The best way to explore Key West is on a road trip from Miami. Driving over the long bridges connecting the different islands is definitely a bucket list experience. Click here to search all the car rental agencies and get the best price for your road trip.

1. Visit Mallory Square

things to do in key west sunset mallory square

Definitely the most popular thing to do in Key West is to watch the sun set from Mallory Square. How do I know this? All I have to do is look at the crowds! Each night a sunset celebration takes place overlooking the Harbor from Mallory Square. Street performers put on some dazzling shows as crowds form along the large square. It’s a fun place to hang out, but be sure to bring some small bills or change to tip the performers, they work hard for their money.

2. Mallory Square Attractions

Mallory Square in Key West

There are many things to see at Mallory Square, so make sure to explore it during the day. Take a walk down to the waterfront and then enjoy seeing many of the top Key West attractions here.

  • The Maritime Museum – The Mel Fisher Heritage Maritime Museum displays many artifacts from the 17th-century ships that went down on the coral reef.
  • The Waterfront Playhouse – The longest-running theatre in Florida has nightly rotating shows all year long.
  • Key West Shipwreck and Treasure Museum – There’s a 65-foot lookout tower, shipwreck artifacts and actors recreating the 17th century feel dressed in period clothing. Book your ticket in advance w
  • The memorial sculpture garden is located directly in front paying tribute to famous patrons of the theatre and residents. Take a stroll through the lines of sculptures of famous residents including pusts of Ernest Hemingway, Harry S Truman, Tennessee Williams, and many other important people.

3. Take a Schooner Sunset Sail

schooner sunset sail - key west things to do

If you want to take sunset a step further, take a sunset cruise on a schooner. Key West has a rich history, so feel like you have stepped back in time while enjoying views of the Florida Keys. You’ll see Fort Zachary Taylor, the Sand Key Reef, Mallory Square, and Sunset Pier from the deck of this from one of the finest boats on the schooner fleet.

  • Book this top-rated tour here free from worries as tours can be canceled up to 24 hours in advance with a full refund.

4. Pedal the Key West Hydrobikes

Glow tour on Aqua Bikes in Key West

Another fun way to see the sunset in Key West is to hop on a tour with Key West Hydrobikes, Like everything in Key West, drinks flow freely, so you can even bring two drinks with you to enjoy a toast on the water at sunset. The city has an open drink policy so grab a couple of rum cocktails to put into the drink holders.

If paddling a waterbike isn’t your thing, be sure to hop on one of the many sunset cruises.

  • Look for tours here with Get Your Guide to find your choice of floating bars, schooners, and catamarans that will take you out to watch the stunning sunsets. They offer last-minute bookings and full refunds on cancellations within 24 hours of the tour.

5. Bar Hop on Duval Street, Key West

key west nightlife duval street

Key West was made for partying. Once the sun goes down, you’ll be hard-pressed to find a sober tourist especially downtown in the party district. Duval Street is the main bar and nightlife street and barhopping is a way of life when visiting the Keys.

If you want to join a tour of Duval Street to see the top bars and restaurants while making new friends, check out this fantastic pub crawl tour that stops at five top rated pubs with a cocktail at each stop. And you will get the T-shirt to boot!

Key West Wine-O Bar
Crowne Plaza Hotel’s Wine-O Bar

From upscale wine bars to dive bars, it has it all. There are the staples like Jimmy Buffet’s Margaritaville, (which Dave and I had to visit on our first trip) and the Hard Rock Cafe. But a few other suggestions are Lucy’s Retired Surf Bar, Sloppy Joes, Virgillios, Rick’s Café, and our personal favorite The Wine O Bar and Lounge.

6. Enjoy the Thrill of Dolphin Watching

Dolphin Watching in Key West

200 bottlenose dolphins live in the warm waters off the Florida Keys, and having never had human interaction, seeing dolphins in Key West is a wonderful experience.

When booking a dolphin or wildlife tour be sure to use a sustainable recognized tour operator like Honest Eco Tours based out of Key West or You Can book this Dolphin Watch and Snorkeling Tour in Advance.

7. Stop at the Southernmost Point

things to do in key west southernmost point

No trip to Key West would be complete without a stop at one of the most popular Key West attractions the Southernmost point. It is the southernmost point of the United States mainland! Go early in the morning as the lines are long to take the obligatory selfie at the southernmost point buoy.

The cement marker is located on the southernmost point of the continental United States. With colorful painted lines and writings it lets you know just how close you are to Cuba.

Book a cycling tour of the Key West. Guided tours of Key West will take you through Old Town, the Southernmost Point, Mallory Square, and the Key West Cemetery here. Plus enjoy a delicious slice of Key Lime Pie! Free cancellation and last-minute bookings accepted.

8. Go Parasailing Over the Florida Keys

parasailing key west

The first time we ever tried parasailing was here in Key West and it was so much more fun than we ever expected. Parasailing is the perfect way to see Key West’s beautiful coast. I think a parasailing adventure is certainly one of the most popular things to do in Key West and with good reason.

  • This top-rated parasailing tour aboard a state-of-the-art parasailing boat where you’ll sour high above the Florida Keys.
  • You can book beachside parasailing directly from Smather’s Beach. Check out tours here.
  • There is easy cancellation within 24 hours of departure and you can do last minutes bookings as well.

9. Visit Ernest Hemingway Home

Ernest Hemingway House Key West

From 1931 to 1939 Hemingway called Key West’s old townhome. The highlight of visiting the Ernest Hemingway house is spying the Hemmingway cats. They are everywhere and each cat is said to be a descendant of the six-toed cats that Hemmingway had as pets. Check out their paws, they really do have six toes!

Ernest Hemingway has been everywhere. We’ve visited his old haunts in Kenya, Cuba, Michigan, Paris, and Pamplona so it is pretty special that Hemingway decided to make Key West his home for so long.

10. Climb to the top of the Key West Lighthouse

Key West from Above

Key West’s Lighthouse stands tall over the old town and dates back to 1848. The first lighthouse tower was originally built in 1825 to help ships navigate the coral reef. Cool fact, the lighthouse of 1848’s first keeper was a woman! you can tour the keeper’s quarters before climbing the 88 steps to the top of the Key West Lighthouse for views from the observation deck.

We found that another good bird’s eye view of the island is from the top of the Crown Plaza Concha Hotel that gave us plenty of overhead views too!

11. Ride the Conch Train

Riding the Conch Train in Key West

If you are looking for guided tours to give you the lay of the land, you may want to hop on the Conch Train. This wasn’t exactly for us, but we do admit it gives you a good overview of Key West neighborhoods and highlights.

Book your Conch Train tickets in advance here.

12. Tour the Key West Cemetery

One of the most popular things to see is the Key West Cemetery. Similar to the LaFayette Cemetery of New Orleans, the Key West cemetery has above-ground vaults. One of the most notable tombs is a memorial to the U.S.S. Maine which was blown up in Havana Harbor in 1898.

Book a guided tour of Key West is the Ghosts and Graveyards Tour – See why Key West was named one of the most haunted places in the US.

13. Go Snorkeling in Key West

things to do in Key West - snorkeling
Snorkeling off the coast of Key West

Did you know that Key West has the only living reef in the United States? A lot of people go scuba diving in the Florida Keys as there are plenty of shipwrecks in the area. But if you aren’t certified, the snorkeling is good too!

The John Pennekamp State Park has decent coral to spot wildlife in the Keys. If you’ve never been snorkeling before, this might be a good introduction as the waters are calm and shallow but the reef lacks color and life but the Keys are working hard to bring the reef system back to life and we saw sea turtles, trumpet fish and baracuda.

  • This tour is a great choice where you get to visit two locations on a high speed catamaran. It includes beer, wine and champagne after your are done snorkeling. (Free cancelation within 24 hours of trip)

14. Kayak through the Key West Wildlife Refuge

Sea Kayaking in Key West Florida

I didn’t even know that Key West had such an abundant wildlife refuge. This is one of the oldest wildlife refuges in the country established by Teddy Roosevelt in 1908. It’s a beautiful place to paddle through calm waters watching cormorants, frigate birds, pelicans, and herons fly from the trees.

The best way to explore it is by Sea Kayaking through the mangrove forests on this four-hour eco-tour that includes kayaking, snorkeling, and dolphin watching plus light snacks and a beautiful end to the day at a prime spot for a Key West Sunset.

15. Go On the Key West Eco Tour

Honest Eco Key West Tour
Honest Eco Tours – Key West Fl

For something different, one of the best things to do in Key West is to book a tour with Honest Eco Tours. This full-day tour is a sustainable tour that takes place on the first electric catamaran of its kind in the United States!

It was a full day of snorkeling, kayaking, dolphin spotting, and sightseeing along the coast of Key West. They served a full buffet lunch and gave everyone resuable water bottles making every inch of the tour eco-friend.

  • If you don’t have time for a full day, this 3-hour tour with Get Your Guide include a combination of dolphin watching and snorkeling with the only company in the Florida Keys with the prestigious “Dolphin SMART” certification, a national program that protects and promotes the responsible observance of dolphins.

16. President Harry S. Truman Little White House

President Harry S. Truman Little Whitehouse

We visited Washington DC for the first time two years ago and saw the White House, so it was cool to see the Truman Little White House of Key West. This was President Truman’s winter, White House. This national historic landmark has been used as a retreat for other Presidents as recently as President Clinton.

17. Stroll the Key West Historic Sea Port

Key West Historic Seaport

The old town of Key West is filled with historic structures and a great way to explore the history of Key West is on the waterfront. We love walking along the water and the Historic Sea Port has a beautiful boardwalk to take in the yachts and boat charters.

There are art galleries and boutiques, museums, and boat charters. There are plenty of restaurants along the boardwalk as well. Get yourself a Cuban Coffee at Fisherman Cafe. It was the best coffee we had on the island and it was cheap too! Oh, and be sure to pop into one for a slice of Key Lime Pie.

18. Eat Key Lime Pie

key lime pie key west
Don’t leave without having Key Lime Pie!

It was invented here and you’ll never have one that tastes so good as in Key West itself. One of the best places to try Key Lime Pie is Kermits. You may even find the owner, Kermit himself standing outside on the corner. There is often a large line, so if you don’t want to stand in the heat, never fear, there are plenty of places in Key West to try Key Lime Pie.

19. Fort Zachary Taylor Historic Site

things to do in key west beaches

Fort Zachary Taylor Historic State Park can be visited in conjunction with a tour of the historic fort and a stop at the best beach in Key West. This National Historic Landmark predates the Civil War and gives a glimpse into the lives of soldiers during the Civil and Spanish American Wars. There is a small park entrance fee. Read more: 18 Best Beaches in Florida for Fun in the Sun

20. Key West Distillery

Making Mogitos at the Key West Rum Distillary

The Key West First Legal Rum Distillery dates back to 1900 when it was Jack’s Saloon. After that, it was turned into a Coca Cola Bottling center and there are plenty of antiques and memorabilia dating back to the turn of the 20th century in this building. It’s an excellent tour to learn how the rum is distilled, but it also is a lot of fun to learn about the history of the city.

21. Make Your Own Mojito

Drinking Mohitos in Key West

But it was the chance to make an authentic Cuban Mojito and brought their recipe back for everyone to enjoy. We were in Havana last winter, and we can attest, their mojitos tasted exactly like the classic Cuban Mojito and it will make a rum lover out of you! When you book this experience, you get to bring home your glass and tools to make your own mojitos at home. Make sure you buy a bottle of rum too, it’s delicious!

22. Take a Haunted Pub Crawl

Poster of Key West Weirdos

Key West is consistantly ranked as one of the most haunted cities in America. And with good reason, with so many shipwrecks, cursed treasure, a voodoo pass and a wild west history, there are many stories to be told. One of our favourite things to do is to go on haunted tours.

This top rated tour takes you on a two hour journey through “Cayo Hueso” (Key West). Visit haunted pubs and mansions in the Old Town after dark.

23. Key West Beaches

things to do in key west beaches

We haven’t talked a lot about the beaches of Key West, but there are a few to relax at. We found that we spent more time by the pools of our hotels when not enjoying the Key West attractions, but here are some suggested beaches to visit.

Fort Zachary Taylor Best probably the best beach to visit from downtown. Located within Fort Zachary Taylor Historic Site this is a great stretch of sand popular for snorkeling, paddling, and fishing.

Smather’s Beach is the largest public beach on Key West at a half a mile long. There are lounge chairs umbrellas, and watersports offered.

24. Key West Butterfly & Nature Conservatory

Canadian Museum of Nature Butterflies Ottawa Attractions

The Key West Butterfly & Nature Conservatory is a tranquil stop on any Key West Tour. Not only are there hundreds of butterflies, but you’ll also see flamingoes and other tropical birds. Check out the live webcam here.

25. Key West Roosters

things to do in key west - rooster spotting

When walking around keep an eye out for the many roosters roaming the streets. These roosters came from Cuba and were once used for cockfighting. Today they rule the roost and live a life of leisure. Roosters can be found running around everywhere on lawns, sidewalks and at all of the top Key West attractions.

26. Dry Tortugas National Park

best of key west florida dry tortugas

Located (113km) 70 miles from Key West, the Dry Tortugas is one of the most remote national parks in the United States. The Dry Tortugas was used as a fort between 1845 and 1876. Fort Jefferson was a giant military fort used to defend during the Spanish American War. It takes up almost the entire Garden Key. You can take a day trip out to explore the island and beautiful sandy beaches and you can even camp overnight on Garden Key.

27. Fantasy Fest

Fantasy fest in Key West

If you want to take partying up a notch, visit Key West at the end of October for Fantasy Fest. During our first visit here, we drove down and didn’t even realize it was going on.

Boy, what a shock we had when we walked into our hotel and saw a lot of pained, naked people walking around. Fantasy Fest is like Mardi Gras on steroids. People parade down Duval Street nightly showing off their body paint and works of art. Since it is Key West, there’s a lot of alcohol involved too!

Where to Stay in Key West

Perry Hotel in Key West

Perry Hotel Key West is a quiet retreat on the marina. This boutique hotel has elegant rooms overlooking the waterfront. What we loved about it was the local vibe. Many people from the marina stop into the pool bar for lunch and snacks.

La Concha Crown Plaza is the perfect place to stay in the heart of the action, is located directly on Duval Street. You just have to step out of your door to be near all of the top attractions. The lobby is busy, but it is peaceful inside. There’s a pool for guests only. There is a luxurious rooftop spa and gorgeous sunset views.

If you are looking for an alternative to a Caribbean Island vacation, Key West could be the choice for you. With Highway 1 connecting it to the mainland, United States. it’s an easy way to get to the middle of the Caribbean without having to hop on a flight.

Enjoy our video rounding up the very best things to do in Key West Florida

things to do in key west florida

Enjoy our list of things to do in Key West? Save it to Pinterest for future travel planning.

the very best things to do in key west

Our trip was sponsored by Key West Tourism. All opinions are our own.

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About The Planet D

Dave Bouskill and Debra Corbeil are the owners and founders of The Planet D. After traveling to 115 countries, on all 7 continents over the past 13 years they have become one of the foremost experts in travel. Being recognized as top travel bloggers and influencers by the likes of Forbes Magazine, the Society of American Travel Writers and USA Today has allowed them to become leaders in their field.

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3 thoughts on “27 of the Best Things to Do in Key West, Florida”

  1. Even though I’ve traveled to Ft. Lauderdale almost every year since I was a child, I’ve never made it to Key West! So thanks for the recommendations and extra motivation to add a few days to my next Florida trip so I can finally visit the Keys!