Key West is a gorgeous island in South Florida, located right at the end of the world-famous Florida Keys.
From incredible state parks and kayaking adventures to sunset sails and pub crawls – there is truly something for everyone!
I recently moved to Key West for four months and had the time of my life. But if you’ve never been, I know it can be a little overwhelming trying to figure out what there is to do in this beautiful place.
To help you plan your trip, I have put together this list of my favorite activities for first-time visitors and locals alike.
Table of Contents
- 1. Visit Fort Zachary Taylor State Historic Site
- 2. Explore the Local Art Scene
- 3. Paddle Through Mangroves on an Eco-Kayaking Adventure
- 4. Taste Fresh Seafood at one of the Many Restaurants
- 5. Join a Sunset Cruise
- 6. Visit Some Unique Bars and Restaurants
- 7. See a Movie
- 8. Taste Key Lime Pie
- 9. Catch a Drag Show
- 10. Visit Ernest Hemingway’s House
- 11. Visit Fort East Martello
- 12. Explore One of the Many Beautiful Beaches
- 13. Have a Drink at The Famous Sloppy Joe’s Bar
- 14. Take a Picture With the Southernmost Point Buoy
- 15. Watch the Sunset at Mallory Square Dock
- Bonus: Go on a Food Tour (One of the Best Things to do in Key West for Foodies)
- Now You Know What To Do in Key West
Key West really is one of the best places to visit in Florida, and a top destination in January.
Whether you want an active day or a relaxing one, these are some of the best attractions that Key West has to offer so that you get to experience all that life has in store for you down on the southernmost point of the continental USA.
If you are visiting Key West soon, I recommend checking out this guide on what to pack for Key West.
Here is a list of the top 15 things to do in Key West, Florida. Also, check out our list of 101 must-see places in the US.
1. Visit Fort Zachary Taylor State Historic Site
Fort Zachary Taylor State Park is a great place to be outside on a sunny day in this tropical paradise.
The park has excellent trails, both for hiking and biking, and a historic fort.
The historic fort itself is located along the waterfront of Key West, just off of Southard Street. Founded in 1866, it was constructed in an effort to protect the southern docks from would-be invaders during the American Civil War that was raging at this time.
Although no shots were actually fired here, there are numerous cannons on display, as well as a few other pieces of history you can see inside.
Another exciting thing to know about Fort Zachary Taylor State park is that it is regarded as a great snorkeling spot and one of the best beaches in Key West.
The water on the beach at Fort Zachary is crystal clear, and the marine life is very interesting to observe. If you’re looking for a relaxing day at the beach, this is the place to go.
2. Explore the Local Art Scene
The local art scene in Old Town Key West is thriving, with many great galleries and studios to explore.
Head down Whitehead Street or Duval Street to discover the works of local artists, from painters, photographers, and sculptors to potters in both traditional and modern styles.
The best part is that most of these artists frequently create works of art inspired by the island that make for amazing one-in-a-lifetime souvenirs to take home with you.
Some of Key West’s most famous artists are well-represented here in their own studios, but there are also several smaller galleries that have excellent works for you to enjoy and purchase as well.
Pro tip: The souvenir shop at the Key West Butterfly and Nature Conservatory sells amazing Key West-inspired art for a fair price. They even mail the pieces to your home if you need them to.
3. Paddle Through Mangroves on an Eco-Kayaking Adventure
Experience the mangroves and seagrass of the Florida Keys in an eco-kayak.
Mangrove ecoscapes are filled with plant, bird, fish, and animal life only found in these habitats. These protected areas are known as nursery grounds for many marine species.
The mangroves near Key West are some of the most protected in Florida, and a kayaking excursion is a great way to get up close. You may even be lucky enough to see a manatee or two.
Have a look at this affordable kayak trip which is approximately 2 hours long and includes a knowledgeable guide, equipment, safety briefing and is even dog friendly!
If you’d rather spend a bit longer on the water, this highly-rated day trip is around 6 hours — but first, you’re swept away to clear waters in a catamaran! After you reach the beautiful place, then you will start your paddle trip. Look for dolphins, stingrays, turtles and manatees from your kayak.
4. Taste Fresh Seafood at one of the Many Restaurants
Try a fresh seafood dish along Duval Street paired with a Key West cocktail.
From fish to conch, you’re sure to find anything and everything that the water has to offer in the many incredible restaurants on the island, so make sure to try some of the local catch.
Some of Key West’s most traditional seafood includes all things conch, like conch salad, conch fritters, conch chowder, and cracked conch. Besides, you can even get to try a conch margarita! It tastes better than it sounds, trust me.
If you’re more of a lobster type of person, try some Key West lobster roll or lobster bisque. I am absolutely sure that you will love it.
Some of the restaurants I recommend on Duval Street are DJ’s Clam Shack, Bagatelle, Caroline’s Cafe and Ocean Grill and bar.
5. Join a Sunset Cruise
Key West boasts some of America’s best sailing waters, making it a true paradise for any fan of the great outdoors.
Set sail on a sunset cruise as you watch endless shades of purple, pink, orange, and red spread across the sky. My favorite thing about Key West sunset cruises is that they always have great food and an open bar. Also, when I went, the crew was just fantastic.
Have a look at this top sunset sail on a 70-foot catamaran. The trip lasts around 2 hours and includes excellent appetizers, wine, sparkling wine, freshly made sangria and beer. This sunset trip is of excellent value. Learn more here.
Maybe you’d prefer to set sail into the sunset on an actual sailboat? This small-group trip lasts around 2 hours and includes 8 different wine samplings or 5 different beers. Plus, a selection of gourmet cheeses, meats, crackers, fruits and more. Learn about the trip here.
6. Visit Some Unique Bars and Restaurants
Key West has many excellent bars and restaurants to visit, especially those around Old Town Key West.
Take your pick from a variety of dive bars, sports bars, and nightclubs where you can dance the night away or just relax with friends over a Key Lime Mojito.
Stop by Blue Heaven for a meal of world-famous conch fritters and then head over to Captain Tony’s Saloon on the same block for live music that will keep you swaying long into the night.
After, head to the famous Green Parrot Bar, one of America’s oldest bars, to finish the night on a golden note.
7. See a Movie
Located in the heart of Old Town Key West, the Tropic Cinema is one of only two indoor theaters in all of Monroe County.
The cinema opened in 2004 and aims to bring quality movies to people who long for something more than Hollywood blockbusters — with plush seating and a concession that includes beer, wine and popcorn with real butter, it’s a great place to beat the heat!
When living in Key West, this is the place to see independent films, classics and unique shows. In keeping with the area, the theater has an unmissable aqua-blue Art Deco facade, a sculpture of Marilyn Monroe and a Hollywood Walk of Fame, with a twist.
The Tropic Cinema is a pretty cool place to experience and a unique thing to do in Key West. Find out more here.
8. Taste Key Lime Pie
Mallory Square Dock is a must-see for foodie travelers when visiting Key West.
The waterfront square hosts nightly sunset celebrations with an open-air market filled with local artists selling products and delicious food such as the traditional Key Lime Pie.
Key Lime Pie was invented in the Florida Keys and is the island’s most traditional dessert, so you can’t leave Key West without trying it.
If you have already had your share of the classic pie, try the chocolate-dipped Key Lime Pie or even Key Lime Pie on a stick (my fave).
Another option is to combine a little bit of exercise with a slice of pie. On this relaxed bicycle tour of Key West, you’ll learn all about the history of Key West, while taking photos and enjoying the views — at the end, you’ll enjoy a slice of key lime pie! Find out more here.
9. Catch a Drag Show
Drag shows are a Key West classic! They often feature some of the most talented performers in a fun bar atmosphere that you’ll have to see to believe. Check out Bourbon St. Pub and Parade Lounge.
Bourbon Street Singers perform every Friday and Saturday night and make for a truly enjoyable time! They always make unique and hilarious interpretations of popular songs that everyone knows.
Also, to make the nights even more enjoyable, the pub hosts nightly drink specials and boasts an impressive dance floor with bumping music to get your groove on. Learn more here.
10. Visit Ernest Hemingway’s House
The Hemingway House contains an extensive collection of artifacts and gifts that Ernest Hemingway received throughout his career and has now been turned into a museum in his honor.
Also, it offers the rare opportunity to see the inside of a well-preserved Key West home from the 19th century and learn about the life of one of America’s most celebrated authors.
If you’d like to learn more about the life of Ernest Hemingway, this walking tour (which includes food!) takes you to all of the places that he visited in Key West.
Some spots include where he refereed boxing matches, where his boat was kept, his first apartment, and where his books were sold. Of course, the museum and Hemingway House are also included. Find out more here.
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11. Visit Fort East Martello
Fort East Martello is a famous historical site and museum in Key West that was initially built as a Civil War fort.
The original structure of the tower is still visible but today contains many interesting artifacts and art exhibits related to its history.
One of the most curious things about Fort East Martello is that it is home to Robert The Doll.
Robert The Doll is a toy believed to be haunted, as his owner and creator, Robert Eugene Otto reported that it would move its head around at night when the family was not home. It is the doll that inspired horror movies such as Child’s Play and Anabelle.
12. Explore One of the Many Beautiful Beaches
Smathers Beach is one of the most popular beaches in Key West. The sunny white sand and calm waters make it a perfect place to relax after soaking up all that culture on Duval Street.
Smathers is best for sunbathing and practicing water sports. You’ll find public bathrooms and showers, chair and umbrella rentals, watersport rentals, and food trucks.
Higgs Beach is great for snorkeling but only along the break wall. Amenities include children’s playgrounds, a dog park, tennis and volleyball courts, restrooms, and showers.
South Beach is more of a lazing around kind of beach — I never saw many people swimming here. You’ll find chairs available to rent and a pretty cute seaside café.
Fort Zachary Taylor is a good place for snorkeling, paddling and scuba diving as well. Snorkel equipment is available for rent, plus you’ll find bathrooms, showers, and a café. Water shoes are recommended!
13. Have a Drink at The Famous Sloppy Joe’s Bar
Sloppy Joe’s Bar is for sure one of the most popular bars to visit in Key West!
Not only does it have a fun atmosphere, but it’s also rumored that Ernest Hemingway used to spend time there when he was in town.
Today, it is home to what locals consider to be the “best damn” key lime pie on the island and hosts live music and dancing every night of the week.
14. Take a Picture With the Southernmost Point Buoy
The Southernmost Point Buoy is a famous landmark in Key West. Located at the edge of Key West, this buoy marks the southernmost point in the continental United States.
People from all over the country and the world travel to take pictures with this symbolic icon.
My tip is: get there as early as you can! As with any popular Instagram spot, the Southernmost Point Buoy gets crazy lines and the best time to avoid them is early in the morning.
15. Watch the Sunset at Mallory Square Dock
Last but not least, is watching the sunset at the previously mentioned Mallory Square.
Once the sun sets, Mallory Square is a gathering place for locals and tourists alike to come together to watch a vibrant outdoor show.
Thousands of people gather around to enjoy performers such as musicians, mimes, jugglers and hula hoop artists that put on a beautiful performance right before the sky turns pink and orange and nature’s light disappears behind the horizon.
Mallory Square also hosts some of my favorite bars in Key West like El Mesón de Pepe Bar and Restaurant. I love the vibe at this Cuban restaurant and grabbing a drink after an incredible day in paradise!
Bonus: Go on a Food Tour (One of the Best Things to do in Key West for Foodies)
There is no better way to experience all the amazing food that Key West has to offer than by going on a classic food tour.
I recommend checking out the ones offered by Key West Food Tours, such as the Southernmost Food Tasting & Cultural Walking Tour (view on Viator or Get Your Guide), the Historic Seaport Food & Cultural Walking Tour (view on Viator or Get Your Guide) and the super fun Key West Pub Crawl.
Discover the Cuban and Caribbean influences in the food and sample Key West favourites such as conch fritters, key lime pie, fish tacos, and more. Visit Mexican cantinas, family-owned Cuban restaurants, bakeries, and an old speakeasy!
Note: if you have the chance, consider taking a flight from Miami or Ft. Lauderdale and exploring the Exumas in the Bahamas. The beaches and water are incredible! Plus, you’ve probably heard of the famous swimming pigs? Well, they’re located near Staniel Cay and are a must-see!
Now You Know What To Do in Key West
That’s a wrap! Now you know all the best things to do in Key West, Florida, and you are ready to have the time of your life.
I really enjoyed living on this beautiful island, and I love writing about it every time I get a chance to help people that dream of visiting it.
Key West is known as America’s last Caribbean city, so be sure to pack your bags and visit this vibrant island paradise filled with culture, seafood, and fun.
It doesn’t matter if you stay only for the weekend or for several months as I did, you will always discover new things to do. Thanks for reading and best of luck with your trip.
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