30+ Best Things to Do in Key West, Florida

Welcome to Key West — one of my favorite places on the planet! There are so many fun things to do in Key West, Florida, the southernmost city in the contiguous United States. This town is a lively place with something for everyone.

Whether you’re here for Key West’s legendary festivals or nightlife, snorkeling and kayaking adventures, historic sites and museums, or all of the key lime pie (raises hand), you are going to love Key West as much as I do!

I adore Key West and I find something new to do every time I visit.

From following in Hemingway’s footsteps to celebrating the sunset every night, let me show you my favorite things to do in this little slice of heaven in South Florida. 

This post was published in January 2024 and was co-written by Adventurous Kate and Riana Ang-Canning.

Best Things to Do in Key West, Florida

Catch the Sunset Celebration at Mallory Square

The Sunset Celebration was the first thing that I ever did in Key West — and it made me fall in love with the place immediately! Two hours before sunset, locals and visitors gather at Mallory Square for a big party. Enjoy live music and street performers, take in a comedy show, shop from local vendors, and grab a bite (or a frozen cocktail!) from the food trucks on site.

Be sure to check out my favorite — the cat man! He performs an acrobatics show with his cats!

As the sun starts to sink into the Gulf of Mexico, lighting up the sky in pinks and oranges, everyone gathers to take in the view, just like frequent Key West visitors Mark Twain and Tennessee Williams once did. They don’t call Key West “Home of the Sunset” for nothing! 

Stroll Duval Street

Duval Street is Key West’s main drag, where you’ll find plenty of places to eat, drink and shop. Yes, this place is extremely touristy — but that’s the charm of it all. You’ll see plenty of Key West locals and visitors hanging out in the bars, no matter what time of day it is!

Many of Key West’s festivals and parades go down Duval Street, including Fantasy Fest in October and Hemingway Days in July. This street is also where you’ll find the Hemingway House, Mallory Square and the Conch Tour Train, all some of the best things to do in Key West. 

Grab a drink at famous bars like Sloppy Joe’s or Captain Tony’s Saloon, buy a souvenir from one of the many gift shops, enjoy a drag show, browse a local art gallery, and snap a photo of the 1920’s Strand Theater. And you can walk all the way down to Pocket Park and its small beach, a block from the Southernmost Point. Speaking of that…

Visit the Southernmost Point

The southernmost point of the continental United States is found in Key West, where Duval Street meets the Atlantic Ocean. It’s marked by a large red and yellow concrete buoy and you can’t leave Key West without taking a photo next to it. The buoy even has its own live webcam! 

While the Southernmost Point Buoy claims to be the southernmost point of the continental US, that might not technically be the truth. Points on Fort Zachary Taylor, Truman Annex US Navy property, and Ballast Key all appear to be a bit farther south — but none of them have a large buoy for a photo op! 

Try all the key lime pie

Every time I’m in the Florida Keys, I eat my way through the key lime pies, all the way from Key Largo to Key West. You might think that might get boring, but there is so much variation to them!

While the exact origin of key lime pie is up for debate, what’s not up for debate is how delicious this dessert is and how well it showcases the tiny key limes indigenous to the Florida Keys.

Some of the most beloved key lime pies in Key West come from Key Lime Pie Bakery, Kermit’s Key Lime Shop, Blue Heaven, and The Cafe. Go ahead and try them all!

And at the Key West Key Lime Pie Company, you can try their delicious pies, or even make a tiny key lime pie of your own! They offer classes on Thursday and Friday mornings (though it’s most of an assemble-your-own-pie class than a bake-everything-from-scratch class).

Visit the Ernest Hemingway Home and Museum (and say hi to the cats!)

Ernest Hemingway, one of the greatest 20th Century writers, was once a Key West resident. He first visited the island in 1928 and finished his WWI novel, A Farewell To Arms, while in Key West. 

Hemingway and his then-wife, Pauline, fell in love with Key West and decided to settle down in what is now a National Historic Landmark: the Hemingway Home and Museum. 

The Hemingway House is full of personal touches from the Hemingway family, such as antiques collected during their time in Europe and the studio where Ernest Hemingway did some of his best writing — when he wasn’t out fishing off Key West, a favorite pastime of his. 

It’s also home to the famous six-toed polydactyl cats. Hemingway was given a six-toed cat by a sea captain during his time in Key West and descendants of that cat — many of whom also have six toes — still roam around the house today. If you’re a cat person like me, you must come here!

The home and museum are open daily from 9:00 AM-5:00 PM. Tickets cost $18 per adult or $7 per child ages 6-12 (kids under five are free). Tickets include a guided tour. 

Want a deeper dive into Hemingway? There’s a Hemingway-themed food and history tour you can join! (And if you come visit for Hemingway Days in July, BOY is that a fun festival! The Hemingway lookalike contest is one of my favorite festivals I’ve ever attended while traveling!)

Visit the Harry S. Truman Little White House 

I expected the Hemingway house to be my favorite historic site in Key West — but it was actually the Little White House! I loved my visit to this little time capsule from the mid-20th century. After serving as a naval base in the late 19th and early 20th Centuries, this house was used as a winter residence for President Truman, who loved Key West.

Many other presidents and distinguished guests have stayed in the house over the years, such as Thomas Edison during WWI, President John F. Kennedy during the Bay of Pigs incident, and President Eisenhower while recovering from a heart attack. More recently, in 2001 Colin Powell held talks between the leaders of Armenia and Azerbaijan.

I loved the mid-century designs, and how the furnishings were surprisingly modest for a president. And I especially loved the poker table — Truman loved playing poker with his cabinet, but it had to be kept secret because it would be a scandal if the public knew the president was gambling!

Today, the house is still used for presidential functions, but otherwise operates as a museum for the public. Guided tours leave every 20 minutes and the guides do an incredible job bringing the history of the building to life. 

The Little White House is open daily from 9:30 AM-4:30 PM. Tickets cost $24.67/adult, $10.75/child aged 4-12, and children under four are free. You can buy tickets here.

Take a walking tour of Key West

Going on a walking tour is an excellent way to get to know a new place, and Key West has all kinds of themed tours you can take. In fact, I’d say a walking tour is one of the best things to do in Key West, as there’s truly one for every interest.

A few noteworthy walking tours include the top-rated Hemingway Food and Walking Tour, where you can follow in Ernest Hemingway’s footsteps as you learn about Key West history and sample chicken street tacos, conch fritters and key lime pie. 

If you’re into architecture or just enjoy looking at cool homes like I do, you will LOVE Key West — and this Key West Historic Homes and Island History walking tour is a lot of fun!

And of course, I can’t not mention the Jimmy Buffet tour of Key West! For die-hard Parrotheads and anyone who has “Margaritaville” stuck on a loop in their head, discover all of the places that inspired Jimmy Buffett’s songs in Key West, including the site of his first gig, his favorite bars, and even his recording studio. 

Key West also has a pretty spooky history, and a collection of ghost tours to match. Join a guided walking tour to learn about the city’s spooky history, get to know famous ghosts and graveyards when you ride the Trolley of the Doomed, and if you like your boos with a side of booze — or your spirits with a side of, well, spirits? — there’s a ghost tour pub crawl. 

Tour Key West by train or trolley 

Another great way to get to know Key West is by train or trolley. This is an especially good choice if someone you’re traveling with has limited mobility or doesn’t want to spend the whole day on their feet.

The Key West Conch Tour Train has run through Key West since 1958 and has transported more than 15 million people in that time. It’s not a train on tracks; it’s more of a long line of seats pulled by a train-shaped engine. On this 75-minute train tour through the Conch Republic, you can learn about Key West’s history and famous residents. 

Another good option for getting around Key West without having to walk too far is the Key West Hop-On Hop-Off Trolley Tour. A one- or two-day pass takes you around more than 100 Key West attractions — with interesting narration along the way.

And if you’d rather tour Key West with private guide, check out the private pedi-cab tour, which can be customized to your preferences.

Explore Key West by Bike

Key West is an excellent destination to explore by bike, even if you’re not ordinarily a bike tour kind of person. The island is extremely flat, and most of the areas have limited traffic rather than a constant terrifying stream of cars.

You can discover the highlights of Old Town Key West on this three-hour guided bike tour, which takes in sights like Mallory Square, the Southernmost Point, Mile Marker Zero, and the White Street Pier. Helmets and water are provided.

Go on a sunset boat tour 

I do think you should spend one sunset at Mallory Square — and another sunset out on a boat! On my first trip to Key West, I did a sunset sailing cruise with an open bar, and BOY was that a fun night!

(Amusingly, that boat happened to be full of Boston sports fans decked out in Red Sox and Patriots gear. I’m from Boston, Gronk was apparently on a boat nearby, and it led to a LOT of bonding and we finished the night at Kevin’s Irish Pub! I’m still Facebook friends with some of those people!)

There is a huge variety of sunset cruises in Key West. Some are booze cruises, while others are more relaxed. It’s important to find the right cruise for you.

If you’re interested in an open bar sunset catamaran cruise like mine, take a look at this one. It includes live music and appetizers as well.

A similar option is the Key West Sunset Sail, which is also a catamaran with an open bar, but also has live music by local musicians, and hearty appetizers like peel-and-eat shrimp.

The tiki bar boat cruise is BYOB — any booze you want, you must bring, and it’s a small boat with a maximum of six people. A fun choice if your group wants the boat to yourselves (but book early for that).

The sunset sail and dolphin watching cruise is a more relaxed option, and it includes wine and tapas.

And if you’d like to combine snorkeling and sunset, check out the Rum n’ Reggae snorkel and sail. 

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Visit Judy Blume’s Bookstore

Did you know that beloved children’s author Judy Blume lives in Key West — AND co-founded a bookstore here? Books & Books is an independent, nonprofit bookstore located on the corner of Eaton and Simonton Streets, right in the heart of Key West.

At Books & Books you’ll find a wide selection of books across all kinds of genres, as well as a full schedule of events, literary and otherwise. I often enjoy picking up a book by a local author as a souvenir, and this couldn’t be a better place to do it!

And of course — if you do happen to run into the fabulous Ms. Blume herself, please be respectful.

Explore Key West by water

Your water adventures in Key West don’t have to stop with boat tours and cruises. There are lots of water sports and aquatic activities you can enjoy.

How about snorkeling? So much underwater wildlife lurks just off shore! You can try a half-day snorkeling excursion on a reef just off Key West. There’s also a snorkeling tour with breakfast and unlimited mimosas.

Anything else? You can explore the Florida coast on a 90 minute guided jet ski tour or spend the day on a water sports catamaran and try kayaking, snorkeling, parasailing and jet skiing.

You can also learn to SNUBA — a cross between scuba diving and snorkeling with no prior experience required — which is definitely one of the cooler things to do in Key West.

Go kayaking or paddling

If you’re interested in doing a bit of paddling, Key West offers lots of opportunities to kayak through the mangroves, along sandy beaches or in the clear waters at night. 

Head out on a two-hour guided Key West Mangrove Kayak Eco Tour, paddle further on a three-hour mangrove maze guided tour, or spend a half-day sipping drinks on the sandbar, snorkeling with sea turtles and kayaking through the mangroves during Key West’s Ultimate Sandbar Adventure.

And if you’d rather do your own thing without a guide, you can always book a half-day kayak rental — ideal for people who would rather explore independently.

Now if you want to do something REALLY cool, sign up for a Night Glow Kayak Paddle Session! I did this in Key West and it was so cool! You float on the water in a glass-bottomed kayak lit up with LED lights, so you can see the underwater wildlife that you never get to see by day! It’s one of the most unique things to do in Key West. 

Visit Key West beaches

How have we come this far in the post and not talked about Key West’s beaches? There are, as you’d expect, some really nice beaches in town. Smathers Beach and Higgs Beach especially deserve a visit.

Smathers Beach is the largest public beach in Key West and perfect for swimming or relaxing under a palm tree. There are lots of facilities, food vendors and water activities to enjoy. Being such a beautiful and accessible beach, Smathers can get crowded, especially during spring break.

Higgs Beach, on the other hand, is much less popular, despite being closer to Old Town Key West. In addition to a sandy beach and palm trees, Higgs Beach is also home to picturesque piers, a civil war era fort, and the African Refugee Memorial and burial site.

Fort Zachary Taylor Historic State Park, located in the westernmost part of the island, also has a lovely beach to explore, with some snorkeling just off shore. There are also walking paths, bicycle trails, and a cafe.

Climb the Key West Lighthouse

The Key West Lighthouse was first opened in 1848 to guide military and commercial vessels through the coral reefs. Fun fact: the first lighthouse keeper was a woman named Barbara Mabrity! This was extremely rare in the 19th Century.

Today, the lighthouse operates as a museum showcasing the area’s maritime history and offering a beautiful view off the coast. The museum is open daily from 10:00 AM-5:00 PM. 

Entrance costs $17 for adults, $13 for seniors, locals, college students with ID and retired military service members, $9 for youth ages 7-18, and free for children under seven or active military service members. Discounts are available if you book your tickets online. 

Visit more cultural sights in Key West

There is lots more culture, history and natural beauty to explore in Key West. Here are a few more places to add to your Key West itinerary: 

The Key West Butterfly and Nature Conservatory is home to over 50 butterfly species plus exotic birds and more, while the Audubon House and Gardens features a 1840s home filled antiques and the lush gardens that surround it.

The Key West Aquarium is a great place to learn about marine life, with a Touch Tank, lots of aquatic wildlife, and regular conservation talks. The Florida Keys Eco-Discovery Center is another great place to learn about tropical plants and animals.

For something a bit different, head to the Key West Cemetery. I’m a big fan of the quirky headstones! You can also tour the Key West First Legal Rum Distillery and enjoy rum tastings and a mojito making class.  

And if you’re into shipwrecks, you’re in luck. You can visit the Mel Fisher Maritime Museum and see what they’ve recovered from 17th Century shipwrecks and then head over to the Key West Shipwreck Museum to discover 400 years of shipwrecks off the coast of the Florida Keys. 

Go on a Key West food tour

Key West cuisine is about more than just key lime pie! It’s also well known for its fresh seafood, Bahamian food, and Cuban food. Food tours are one of my favorite activities to do anywhere, and Key West is no exception.

Explore the mom and pop eateries of Old Town Key West on a three-hour food and culture tour, sample tasty seafood and get a history lesson on this three-hour food tour through the Key West Historic Seaport, or figure out where the locals eat on this 2.5-hour secret food tour.  

Go fishing

Take part in one of Ernest Hemingway’s favorite Key West pastimes and head out on a fishing expedition. Whether you’re fishing for fun or for your dinner, this is a Florida Keys must-do activity. 

Set sail on a 64′ catamaran for a half day fishing tour through the Florida Keys, perfect for the whole family, or try your hand at deep-sea fishing on this six hour Gulfstream Fishing Tour. 

For experienced anglers, join a sportfishing charter for you and five friends to see who can reel in the biggest catch of the day. 

Enjoy Key West’s legendary nightlife

Just because Key West is the “Home of the Sunset,” that doesn’t mean the party stops when the sun goes down. In fact, for many Key West visitors, it’s just getting started! 

Duval Street is the main drag for nightlife, and you might find yourself singing along with Parrotheads at Margaritaville or dancing at Sloppy Joe’s. Or, if you meet a rollicking group of Bostonians on your sunset cruise, you might end up at Irish Kevin’s, just in time for the Guinness chugging contest.

Want to meet new friends on your nightlife journey? Check out a Key West craft cocktail crawl.

You can even get on the other side of the bar in a tiki cocktail class, where you’ll learn to make four different drinks and enjoy a rum tasting!  

Take a SUP Yoga Class

On one of my trips to Key West, one of the surprising highlights was a SUP yoga class, done on a paddleboard out on the water, surrounded by mangroves. Lazy Dog Yoga offers both yoga classes and eco tours, on Stock Island, just east of Key West.

You don’t have to be a hardcore yogi to enjoy this class — it’s for all levels. Even if you’re new to yoga, you’ll appreciate how much holding poses on a paddle board helps your core strength!

This is a great option for a morning class, before it gets too hot for the day — but you might not want to plan it for the morning after your booze cruise.

Take a Day Trip to Dry Tortugas National Park 

Dry Tortugas National Park is a collection of small islands just west of Key West, accessible only by boat or air. These islands make up a unique national park in the US, thanks to their remote location, and access is limited.

Once at Dry Tortugas, you can spend your time exploring Fort Jefferson, snorkeling off the keys, swimming and enjoying the beautiful scenery. The white sand beaches at Dry Tortugas are gorgeous — some of the best beaches in the Florida Keys.

There is only one public ferry to Dry Tortugas National Park and one seaplane company that flies there, so you’ll want to book as soon as you have your trip dates. (Trust me — I’ve wanted to go to Dry Tortugas every time I’ve been in Key West, and they’ve always been sold out.) You can find the ferry information here.

Attend one of Key West’s legendary festivals

Key West is one of the most festival-driven cities in the United States, and it’s so worth coming to celebrate! Just keep in mind that festival times bring sky-high prices and limited availability. Book early, because a lot of regulars book their accommodation a full year out.

So what festivals should you know about? Here are a few:

Key West Songwriters’ Festival (May) — Did you know that Key West is home to the largest songwriters’ festival in the world? Expect performances from all kinds of genres here!

Key West Pride (June) — Key West is one of the most fabulously queer destinations in the United States, and Pride is off the hook! There’s a huge parade here, along with plenty of drag shows, performances, and even a vibrator race (don’t ask).

Hemingway Days (July) — I attended Hemingway Days, a tribute to Ernest Hemingway, including the Hemingway Lookalike Contest, which is one of the funniest events I have ever witnessed. There’s also a bull run!

Fantasy Fest (October) — The 10 days leading up to Halloween are filled with parades, balls, and all kinds of costumed events — most of them VERY much adults-only. Expect elaborate costumes, more than a bit of nudity, and sharing the island with 75,000 of your new best friends.

The Bight Before Christmas (late November through December) — The month leading up to Christmas is filled with all kinds of events from people who know that you don’t need it to be a White Christmas to enjoy it! The Lighted Boat Parade is the major event of the season.

How Much Time to Spend in Key West

I recommend giving yourself a minimum of three days in Key West to enjoy all of the sights. There are so many cool things to do in Key West, as you by now surely know, but this isn’t a destination where you want to run yourself ragged checking every attraction off your list. Part of the fun here is the chilling out.

That said, if you want to spend longer than three days here, you absolutely can. (And enough people spend the whole winter season here!)

I would happily visit Key West for a week or so, and that gives you time to do more day trips — not just Dry Tortugas, but perhaps up the Overseas Highway toward Marathon and back.

Personally, I think the best Florida Keys trip would split a few days in Key West with a few days in the Upper Keys — both Key Largo and Islamorada are great options.

How to Get to Key West

The easiest way to get to Key West is to fly into Key West International Airport, which has direct flights from many cities in the Eastern US. If you don’t have a direct flight, there are plenty of connections.

Otherwise, you can fly into Miami International Airport, which has extensive connections both nationally and internationally. From Miami it’s a 3.5-hour drive to Key West, and if you have a rental car, I definitely recommend spending time in Keys along the way.

If you don’t have a rental car and want transportation from Miami to Key West, this private shuttle from Miami to Key West comes highly rated.

Where to Stay in Key West

Key West has no shortage of hotels, motels, inns and resorts for your stay. Accommodation here can get quite expensive, thanks to Key West being a small geographic area with a lot of tourism.

Here are the top-rated places to stay in Key West:

Top-Rated Luxury Hotel in Key West — Parrot Key Hotel & Villas is a gorgeous resort on Florida Bay featuring four pools, on-site dining, and activities like kayaking and massages. They also offer a complimentary shuttle to Old Town Key West. 

Top-Rated Mid-range Hotel in Key West — Simonton Court Historic Inn & Cottages is an adults-only inn with tons of character, just minutes from Key West’s top attractions. There are four on-site pools and all rooms have a balcony or patio.  

Top-Rated Budget Hotel in Key West — Blue Marlin Motel is a simple motel with clean rooms a short walk from the action on Duval Street, and offers a continental breakfast and heated outdoor pool for guests. 

Find deals on places to stay in Key West here.

Best Time to Visit Key West

In my opinion, the best time to visit Key West is the spring: think March, April and May. At this time you have warm, summery days without the overbearing humidity of the summer months, and the weather is perfect for swimming and snorkeling.

Key West can be very busy in the winter months, and it can get chilly at night — don’t forget a light jacket! Summer can be incredibly hot and humid, and if I hadn’t been visiting for Hemingway Days in July, I would not have wanted to go at that time of year at all. But it depends on your personal tolerance for heat and humidity.

I strongly recommend being very careful about fall trips to Key West, as this coincides with hurricane season. While hurricane season technically runs from June to November, most hurricanes tend to hit Key West in September and early October. If you are in Key West during a severe storm, listen to the authorities and do what they say.

No matter what time of year you decide to visit Key West, book everything on the early side. This is not a destination where you want to rock up last minute with nowhere to stay.

You may also want to visit Key West during one of its famed festivals or special events. You can check out Key West Pride (June), Hemingway Days (July), ​​Fantasy Fest (October), or The Bight Before Christmas (December). Note that prices and crowds surge during any big festivals in Key West, so plan accordingly.

Read More: The Best Time to Visit Key West

Is Key West Worth It?

I mean, do you think Key West is worth it after reading all these words about how madly in love I am with this destination? Key West is the best! It’s so fun and so friendly and everyone seems to be in the best mood!

Whether you’re visiting on a Florida Keys road trip or just a quick getaway, I think you’ll really love your time in Key West.

I hope you have the best trip ever! Then come back and tell me all about it!

More on the Florida Keys:

• Ultimate Florida Keys Packing List
• Solo Female Travel in Key West and the Florida Keys: The Ultimate Guide
• 24 Fabulous Things to Do in Key Largo, Florida
• 22 Fun Things to Do in Islamorada, Florida Keys
• Best Time to Visit Key West and the Florida Keys
• 25 Best Florida Keys Beaches
• 11+ Best Beaches in Key Largo
• 13 Best Key Lime Pies in Key West
• A Sizzling Summer Trip to the Florida Keys
• Key West, You Are My New Favorite
• Welcome to the Florida Keys

More on Florida:

• 17 Tips For Your First Trip to Disney World as an Adult
• Seaside, Florida: The Town from The Truman Show is a Real Place
• Miami is Nice, so I’ll Say It Twice

Have you been to Key West? What do you love to do there? Share away!