7 Fun Key West Must-Do Experiences On Your First Visit

Key West Must Do Experiences - Night Kayaking Tour

Are you visiting Key West for the first time? It’s no exaggeration to say that a Key West vacation is a dream come true! Of course, knowing exactly where to go when traveling to Key West is essential for making the most of your time in paradise.

What are the fast facts to know before you visit Key West for your first vacation here? In addition to being the southernmost city in the contiguous United States, Key West is located just 90 miles from Cuba. Key West also boasts year-round warm temperatures and sunshine. While storm season in Key West lasts from June through November, you’ll find plenty of perfect, calm days all throughout summer and fall when you come for your road trip or jet-setting getaway.

As you build your itinerary in Key West Florida, you’ll find that this destination has no shortage of great museums, cultural attractions, beaches, parks, and opportunities for excursions. That includes chances to cruise around the island in search of glimpses of sandbar sunsets and sea life that top anything you’ll see from land.

Ready for your unforgettable trip to the Florida Keys? Here’s your Key West must-do list!


1) Go Night Kayaking In Key West Florida

How’s this for a once-in-a-lifetime experience? When you visit Key West, you can actually book a guided after-dark excursion through the moonlit mangrove tunnels of the Florida Keys!

At Night Kayak Key West, we offer the ultimate item for your Key West bucket list by providing LED-lit kayaks with clear bottoms that provide views of the marine life swimming beneath you as you paddle. Our tour guests enjoy:

  • Well-maintained equipment

  • Exceptional service from highly trained guides

  • Access to the spots where the nocturnal wonders of Key West come alive

  • Affordable rates

As a locally owned and operated Key West night kayaking tour provider, we know how to cover all the planning and preparation needed to give you a top-notch experience. With so many people eager to experience one of the most magical and unforgettable tours available in Key West Florida, openings book up quickly.

Make a plan to cruise in a kayak with us after dark! Book your spot with us for the ultimate Key West must-do experience!

Night Kayak In Key West


2) Visit Dry Tortugas National Park

Dry Tortugas National Park is a unique eco-attraction made up of seven small islands located about 70 miles away from Key West in the Gulf of Mexico. In addition to offering breathtaking views from land, Dry Tortugas is also one of the diving capitals of the world.

Here are some things you must do in Key West when adding this landmark to your list of stops:

  • Visit Civil War-era Fort Jefferson on Garden Key

  • Go kayaking or boarding

  • Go diving or snorkeling among coral

  • Spot birds and sea turtles during wildlife-viewing expeditions

Pro: tip: There’s even an option to camp at Garden Key to enjoy stargazing from what feels like the middle of the ocean! Just be aware that camping at Dry Tortugas should only be done by prepared, experienced campers due to the remote location of the park!

Visit Dry Tortugas National Park


3) Learn About Key West’s Famous People

As you cross items off of your Key West bucket list, you’re going to understand why so many artists and high-profile people have fallen in love with this place throughout modern history. Many have actually left legacies on the island that are still enjoyed by tourists today. Add these spots of interest to your Key West Florida map:

  • The Ernest Hemingway House at 907 Whitehead Street

  • The Harry S. Truman Little White House at 111 Front Street

  • The Tennessee Williams Museum at 513 Truman Avenue

Unfortunately, the home where Shel Silverstein wrote “The Giving Tree” in 1964 was destroyed beyond repair by a banyan tree during Hurricane Irma.

Historic Ernest Hemingway House


4) Tour The Key West Shipwreck Museum

Fans of seafaring should definitely consider a visit to this museum a must-do in Key West! This innovative museum uses actors, films, and actual artifacts as part of an interactive experience that tells stories covering nearly 500 years of shipwreck history in the Florida Keys.

This impeccably done experience truly brings you back in time to an era when hundreds of ships passed the island daily on their way to trade routes.

Key West Shipwreck Museum


5) Join The Nightly Party At Mallory Square

The sunset at Mallory Square is one of the most common items on any Key West bucket list. Show up about an hour before sunset to enjoy a fun celebration that has been going on for decades!

Food vendors and street performers will keep you happy and entertained while you wait for picture-perfect views of the tropical sun going down over the seaport!

Mallory Square's Sunset Celebration


6) Have A Lazy Beach Day During Your Key West Vacation

Key West’s beaches don’t require any introductions! You already know that the beaches here are glistening. However, you may be unsure about the best beach to visit for views, fun, and relaxation.

As the largest public beach in Key West, Smathers Beach is considered the go-to choice. Located on the island’s southern side, this half-mile beach butting up against the Atlantic Ocean always promises lively energy and beautiful views. You can even take advantage of these amenities:

  • Beach volleyball nets

  • Jet-ski rentals

  • Restrooms and showers

  • Volleyball courts

Pro tip: Open from sunrise to sunset, this public beach is a great free addition to any Key West bucket list that lets you enjoy a day of leisure and fun without paying for entry! Don’t skip it if you’re looking for a budget-friendly way to spend an afternoon.

Jet Ski Adventure in Key West


7) Have A Drink In Key West

Enjoying a tropical rum cocktail definitely needs to be on your Key West bucket list if you’re the type to try local libations during a travel adventure. In Key West, getting out on the town for a drink is synonymous with hanging out at the bars and clubs on Duval Street.

Most locals will tell you that a famous Key West watering hole called Sloppy Joe’s is the best place for a drink in Key West. Operating on Duval Street since 1933, Sloppy Joe’s offers live music, dancing, a bar, and a taproom. Notable cocktails from the menu include the Southernmost Munity, Spicy Watermelon Margarita, Frozen Rum Runner, Sloppy Rite, and Key West Lemonade. This bar also hosts fun events and live music.

Drink Cocktails on Duval Street in Key West


Planning Your Florida Key West Vacation – Book One Of Key West’s Best Tours

You should always expect the unexpected when you head to the southernmost point for your vacation! The best way to bring thrills and wonder to your upcoming vacation is to book a guided tour by kayak that brings you to moonlit waters to see a side of the island that few people ever get to experience.

Night Kayak Key West is proud to be Key West’s premier cruise and kayak excursion company. Our tours provide everything you need to safely enjoy fun and adventure while living it up on a Key West Florida honeymoon, family trip, friend getaway, and more.

Our kayaks fill up quickly! Book your adventure with us today!

Night Kayak Key West


1 hour 30 minutes
Group Size
Up to 18

Night Kayak Guided Tour

Get a single or double glass-bottom kayak illuminated with lights and follow our tour guide on this one of a kind, unforgettable and simply magical adventure.

This slow paced, immersive, and very relaxing experience will allow you to see some cool, active at night marine life as you are gliding through crystal clear waters of Key West.

Guests will experience going through narrow mangrove tunnels at night, floating around shallow and calm waters as the tour guide will look for interesting critters for everyone to see.

3 hours
Group Size
1 to 6

Key West Sandbar Trip

Key West sandbars are our local well kept secret. This is where we take our families to hang out and relax on our days off. This is the perk of our island lifestyle. Now we want to share this experience with you.

Turquoise shallow waters, epic picture worthy sights all around you that look like a postcard - that is what you're signing up for!