Skip to Content

Top 20 Things To Do in Key West

Top 20 Things To Do in Key West

All the way south on US1 lies one of our favorite beach vacation spots in the US: Key West. As Florida’s southernmost point, this small island city has so many attractions to offer, from historic homes, pristine beaches, endless water activities, incredible restaurants, and great nightlife. There’s no shortage of great things to do in Key West.

If you love road trips, consider driving from Miami to Key West for the ultimate road trip in the United States.

Just 90 miles north of Cuba, with warm temperatures throughout the entire year. Looking for a laidback, tropical, and cultural trip? Key West is the perfect spot.

Things to Do In Key West, Florida

If you’re looking for all the must-dos in Key West, we’ve put together a list of our favorite spots and activities for your next trip all in one place!

Aerial View of the lower keys and Key West - Road Trip Guide to the Florida Keys

1. Helicopter Ride over the Florida Keys

For a spectacular bird’s eye view of the Florida Keys, hop inside a helicopter for a whirlwind scenic tour. There’s nothing more magical than soaring high above the islands and ocean as you see the Keys from one of the most unique perspectives.

Depending on your timeframe and budget, there are plenty of Key West helicopter tours to choose from. Some tours are great for marine life watching, as you’ll be able to see dolphins, turtles, sharks, and stingrays lurking beneath the water.

A sunset tour of the Keys is another excellent choice. With the sky painted bright orange and pink, you’ll have an incredible time riding a helicopter during sunset.

Hemmingway House Outside Key West Floirda

2. Hemingway Home

As home to one of Key West’s most famous residents, the Hemingway Home was the residence of none other than author Ernest Hemingway. He lived in Old Town Key West for nine years during the 1930s, although he owned the house until he died.

This well-preserved home and museum are filled with Hemingway’s original decor and belongings. The lush outdoor garden is also perfect for a stroll or to escape the blazing Florida heat. Of all the museums in Key West, this is my favorite!

Hemingway Home kids petting cats

You’ll also find dozens of adorable cats running around the property. They love to be petted and often walk beside the visitors as they tour the different rooms of the house.

Aerial View of Mallory Square and cruise ship - Things to do in Key West

3. Mallory Square

Situated in the heart of Key West Old Town, Mallory Square has everything you need for a fun afternoon or evening in Florida. You’ll find dozens of the best restaurants in Key West, boutique shops, and entertaining bars dotted throughout the neighborhood, attracting thousands of locals and visitors each day.

Mallory Square is also great for live entertainment. On most days, you’ll find performers and vendors in the plaza. Come early and grab a seat, as it can get jam-packed towards the end of the night.

However, many people come to Mallory Square for the sunset. Located on the historic waterfront, you’ll have the best panoramic view of those famous, colorful Florida sunsets! There are several great restaurants on the water, and here are some of our favorites.

Related Article: Things to do in Key Largo

Aerial View of the Fort at Dry Tortugas National Park - Day Trips from Key West

4. Dry Tortugas National Park

The Dry Tortugas National Park consists of an archipelago of seven small islands known as the Dry Tortugas Islands. The national park is also home to Fort Jefferson, a red-brick building that was once used as a prison during the Civil War.

Visitors mainly come to Dry Tortugas National Park for the abundant sea life. The colorful coral reef is the least disturbed natural reef in all of the Keys. Besides marine life, you’ll also see plenty of exotic birds flying around the islands. Dry Tortugas National Park is home to almost 300 species of birds, although only eight are commonly seen by visitors.

If you want to visit Dry Tortugas National Park, you’ll have several options for transportation. The easiest and most popular way is to take the ferry, which takes about 2.5 hours each way. Day trips can be expensive, but it’s worth the price to see the untouched beauty of the park.

small pod of dolphins spot on a tour from Key West - Top things to do in Key West Florida

5. Dolphin Watch & Snorkel Tour

One of the most fun day trips you can take is out to the islands and natural marine preserves off of Key West. You can spot dolphins and jump out to do some snorkeling. The snorkeling is not with the dolphins but in shallow waters with some corals and small fish to check out.

We went with Honest Eco-Tours aboard their new electric boat. They take their environment seriously with one of the only electric-powered boats in Key West. Check out Honest Eco Tours here.

6. Explore Duval Street

Dissecting through the middle of Key West, Duval Street is jam-packed with action at almost every hour of the day. Lined with beautifully preserved Victorian houses and mansions, wandering down this mile-long street is one of the best things to do in Key West.

Come for a bite to eat at one of the many gourmet restaurants, including the very first Margaritaville in the US. Shop at the boutiques to pick up designer clothes, handmade gifts, and other souvenirs. Visit a local dive bar to watch the game or unwind with a glass of whiskey. No matter what you’re looking for, Duval Street has a place for you!

If you are still trying to figure out where to go, join the original Key West Pub Crawl. You will visit the best bars in Key West and make new friends with other tourists ready for a drink, and it includes five drinks. Another good tour is the Key West Haunted Pub Crawl and Ghost Tour. This tour does not include drinks though.

Sloppy Joe's Key West Florida at Night

7. Sloppy Joe’s

A visit to Key West wouldn’t be complete without a visit to Sloppy Joe’s, which has been around since 1933. It’s most known for its famous patrons Ernest Hemingway and the infamous rum runner Habana Joe.

Every year Sloppy Joe’s holds a Hemingway lookalike contest that draws a huge crowd. If you’re traveling to Key West in July, check to see when the contest is.

Escape the Florida heat and have one of their famous Sloppy Joe sandwiches and rum drinks, of course. It’s always a good time at Sloppy Joe’s.

Floating tiki bar docked in Key West - Things to do and day trips from Key West

8. Tiki Cruise

If you’re looking for a unique thing to do in Key West, then consider spending the afternoon on a tiki cruise! Essentially, a tiki cruise is a floating bar whipping delicious cocktails and taking you through the crystal-clear waters of the keys.

Your onboard bartender and captain will show you some of the best sights around the coast, and you might even get to spot a turtle or two! We recommend this private Tiki Bar sunset cruise in Key West. If you want to get out on the water longer, you can rent this Key West Tiki boat and cruise to a popular Key West Sand Bar.

Keep in mind that you’re required to bring your own food and alcohol. However, with a refreshing tropical cocktail in your hand and music blasting in the background, you can relax while you drift through the waters with you and your best friends.

If you find yourself in Key Largo, there is a similar tiki cruise. It is one of our favorite tiki bars in Key Largo.

Key West Butterfly & Nature Conservatory kids & family

9. Key West Butterfly & Nature Conservatory

One of the best things to do in Key West with kids is to visit the Key West Butterfly & Nature Conservatory. Both of our kids LOVED it!

As soon as you walk through the doors, there are thousands of butterflies flying around and landing on you. So many gorgeous colorful butterflies and plants.

This isn’t just something for kids. We have been before we had kids and think it is still a must-do Key West activity for everyone! I suggest going right when they open. We got there 15 minutes after opening and spent about 40 minutes there.

wooden boardwalk leading out to Smathers Beach - One of the best beaches in Key West

10. Smathers Beach

No trip to Key West would be complete without a little swimming and sunbathing in the famous Florida waters! Smathers Beach is the largest beach in Key West and is the perfect setting for relaxing or playing in the ocean. If you ask us, it is the best beach in Key West.

Lined with swaying coconut trees, you’ll get a real glimpse of the tropics here. For something more adventurous, you have kayak and paddleboard rentals at your disposal.

However, it’s the sugar-soft sand and calm surf that attract beachgoers. Rent a chair and umbrella, or take a dip in the water for a picture-perfect day in Key West.

Exterior View of the Shipwreck Museum - Things to see in Key West

11. Key West Shipwreck Museum

This living history museum takes you back in time to discover Key West’s maritime heritage. Led by live actors, your tour explores the history and livelihood of the infamous Isaac Allerton ship, which sank off the coast of the Keys in 1856.

You’ll relive the different stories of sailors as they battled the treacherous waves over 150 years ago. Not only will you have a deeper understanding of how Key West became a wealthy city, but you’ll also get to see real treasures excavated during the ship’s discovery.

The biggest highlight of the tour is the 65-foot lookout tower. You’ll be able to climb to the top and participate in the exciting action alongside the wreckers. Buy tickets online here.

Kermit's Key Lime Pie Key West

12. Kermit’s Key Lime Pie

Key Lime Pie, the dessert famous all over the USA, is best when eaten in Key West and Kermit’s Key Lime Pie Shoppe to be exact.

If you can’t make it into the shop you can have a Kermit’s Key Lime Pie shipped to you. You can order the famous pies online. Here is where to find the best Key Lime Pie in Key West. Make sure to bring home a bottle or two of Kermit’s Key Lime juice.

Come grab a slice of Kermit’s famous Key Lime Pie or cool down with a pie on a stick. We loved the chocolate-covered Key Lime Pie. There is also a cafe located on the side that is super popular with locals. We stopped in for lunch and highly recommend it.

Aerial Photo of Fort Zachary Taylor Beach - Things to do in Key West

13. Fort Zachary Taylor Beach

Located on the southern tip of the Florida Keys is one of the state’s most historic national parks. Fort Zachary Taylor was built in 1845, several years before the start of the Civil War. It’s now home to the largest Civil War armament collection on the planet.

A tour of the interior explains how the soldiers once defended the red-brick fort during both the Civil War and the Spanish-American War. Once a month, you’ll find live actors who bring the fort to life with stories and performances.

Besides visiting For Zachary, you can head to the southern point of the park for a beautiful, white-sand beach. On the beach, you can spend the afternoon unwinding with a picnic or swimming in the ocean.

Exterior view of the Harry Truman Little White House in Key West - Top Tourist Attractions

14. Harry Truman House

Step inside the winter vacation home of the 33rd president of the United States, Harry Truman. It was initially used as command headquarters for the Spanish-American War, WWI, and WWII and then eventually converted into a house in 1946.

Inside, you’ll be able to learn about the house’s extensive history and how it left a mark on Key West. A guided tour will shed even more light on political tensions throughout centuries of conflict. Buy tickets online here.

It’s best to check the calendar online for the museum’s opening schedule. The Harry Truman House is still used as a retreat for some of the world’s top political leaders.

Interior view of the Green Parrot Bar - Things to do in Key West

15. Visit one of the Oldest Bars in Key West

A favorite of both locals and tourists, the Green Parrot has been serving drinks since 1890, making it one of the oldest bars in Key West. This no-frills watering hole may not look like much from the outside, but its kitschy decor and friendly staff make it a worthwhile visit.

The Green Parrot also hosts live music almost daily, with bands and performers coming from all around the world. Whether you’re coming to honky-tonk, blues, or even acoustic ukulele night, you’ll be in for an entertaining visit.

It’s off the main road and the last bar on US1, making it tricky to find. But between the cheap drinks and award-winning music, this is just one of those places you won’t want to miss!

There are a ton of quirky fun bars to check out. Here is our Key West nightlife guide to pave the path for you.

Boat in Negril Parasailing with a colorful parachute

16. Parasailing in Key West

Soar way above the hustle and bustle as you float higher and higher with a parasail! You’ll enjoy a 360-degree view of the emerald-green waters and islands as the warm, tropical breeze blows through your hair.

You can go solo or take one or two of your friends with you for this epic adventure. In Key West, it’s common to spot marine life in the waters below, such as turtles, stingrays, and even dolphins.

Although you may be high above the water, parasailing is actually quite relaxing. It’s one of our favorite things to do in Key West!

Key West Sunset Cruise

16. Key West Sunset Cruise

One of the best places to watch the sunset in Key West is on a catamaran. Pair that catamaran with unlimited drinks and snacks, and you’ve got the perfect ending to the day.

This is the most popular Key West Sunset Cruise that includes unlimited drinks, Hors D’oeuvres, and live music. With over 2,500 five-star reviews.

Black Conch tour train driving on the streets of Key West - Top Tourist Attractions

17. Conch Tour Train

Explore all the best sights and attractions with a leisurely ride aboard the Conch Train! This Key West tradition dates back to 1958 and takes visitors on a narrated journey through Key West’s history.

Your lively conductor will tell stories about the city’s most famous residents, like Ernest Hemingway, Harry Truman, and even Tennessee Williams. You’ll also learn about the pirates and shipwreckers that put Key West on the map as one of the biggest maritime cities in Florida.

The tour starts in Old Town Key West and makes stops at Front Square Depot, Truman and Duval Depot, and Sails to Rails Museum. Buy tickets online here.

Key West Lighthouse

18. Key West Lighthouse

The 73-foot-tall lighthouse is one of the most iconic landmarks in Key West. Although the original lighthouse was destroyed in the Great Havana Hurricane in 1846, a new one was eventually built several years later.

Due to modern technological advancements, there was no need for a keeper in the lighthouse. It was decommissioned in 1969 and turned into a Key West historic landmark.

Today, you can climb 88 steps to the top to see the original working light. It’s also a small museum with photographs, stories, and other personal belongings from past lighthouse keepers.

woman standing in front of the mile marker 0 in Key West Florida - Road Trip Itinerary

19. Mile Marker Zero

When you visit Mile Marker Zero, you’ve officially made it to the end of one of the longest highways in America! This signpost signifies the start (or the end) of US1, which connects the south of Florida to the northern tip of Maine next to the Canadian border.

Although there isn’t much to do here, Mile Marker Zero makes a wonderful photo opportunity. It can be quite busy during the day, so expect a line of other visitors eager to pose in front of the sign.

woman in a striped dress standing next to the "Southernmost Point" Marker Buoy - top tourist attractions while driving to key west florida

20. Southernmost Point Marker

In Key West, you must take a trip to the southernmost part of the United States. This large, painted buoy sits at the corner of South Street and Whitehead Street and is one of the most popular tourist attractions in the city.

The buoy replaced an old wooden sign that hung since 1970. It survived several hurricanes, but the paint was partially destroyed in 2017 during Hurricane Irma. However, it was repainted by a local artist and stands brighter than ever today.

There is property owned by the US Navy and a small southern island that is believed to be even further south than the buoy. Although it’s debatable whether the marker is actually the southernmost point, it’s still worth a visit and a photograph.

Related Article: Best Cuban Food in Key West 

Latitudes Sunset Key Restaurant at Sunset

21. Lunch or Dinner at Latitudes on Sunset Key

One of the best restaurants in Key West is Latitudes, which is located on Sunset Key. As the name suggests, it’s a great spot for sunset. If possible, coordinate your dinner reservations with Sunset. It’s best to be seated at least 30 minutes before sunset.

Reservations are required. When boarding the free shuttle boat to Sunset Key, they’ll confirm your reservations. You can make reservations online here on Open Table. If you want dinner reservations, you’ll need to make them months in advance, especially during the high season.

If dinner reservations are fully booked up, consider going for lunch. The food and atmosphere are great, and the lunch prices are reasonable.

Related Article: Best Seafood in Key West

Southern Most Beach Resort Key West Florida

Where to Stay in Key West

If you’re road-tripping from Miami to Key West, we suggest spending at least two nights in Key West. As we’ve shown you, there are a ton of things to do in Key West you’ll want to spend a few nights.

We stayed at the Southern Most Beach Resort, which is located right in Key West. This was a great location for us to explore. We could easily walk to dinner, bars, and attractions. During the day, we typically took an Uber to places due to the summer Florida heat, but at night, the temperatures were nice, and we could walk to and from the hotel.

Hotels in Key West sell out during the high season (December- April), so make sure to book well in advance. Check prices online now.

14 Fun Things To Do in Fort Myers

Things to do in Fort Myers featured image woman standing between palm trees on Fort Myers Beach

With an average of 271 sunny days a year there isn’t a bad time to visit Fort Myers. The white sandy beaches are gorgeous, ton of things to do in Fort Myers, tasty restaurants, and much more to offer.