The Key West Watersports Tours You Shouldn’t Skip

Key West is surrounded by water, so this is one town that knows its watersports!   And in order to really experience what the Florida Keys are all about – you need to get on (or in!) that water!

Key West watersports are more varied than  you can imagine, and no matter what you’re looking for, you’ll find it here!  Grab your sunscreen, let’s find out what makes Key West’s waves so awesome.

Jet Ski Tours & Waverunner Tours

Want to see Key West from a different perspective?  Zooming around Key West on a jet ski is one way to accomplish that!  Exploring the beautiful blue waters around Key West is a memorable adventure you won’t want to miss.

Jet Ski Island Tour.  Experience the famous Key West sights from a different perspective on a jet ski with an expert tour guide!  Your guide will take you on a 28-mile tour around Key West, where you will hit hot spots – like the southernmost point – and see wildlife, like dolphins!  You’ll even get to stop at a local sandbar, where you’ll have time to take a swim.

Barefoot Billy’s Jet Ski Tour.  You will have no problem getting yourself to this jet ski tour!  This tour departs from the Marriott Beachside, and includes free to-and-from shuttle service to the location from your hotel!  Enjoy seeing historic Key West from your jet ski, as you ride around the beautiful waters.

Casa Marina Jet Ski Tour. Departing from Casa Marina Resort, this 2-hour guided tour takes you around beautiful Key West.  They provide free shuttle service from your hotel to the resort, and promise an exciting adventure as you learn all about everything Key West has to offer.

SCUBA Diving

Experience the beauty that’s underneath the tropical waters of Key West by scuba diving! Whether you’re a beginner or a seasoned scuba diver, Key West offers many different experiences for every skill level.

Beginner Scuba Diving Tour.  Have you always wanted to explore what’s underneath the beautiful, blue waters around Key West?  Well, here’s your chance!  Geared specifically toward beginners, this tour will have you learning alongside an expert instructor. You’ll be exploring under the sea in no time!  And don’t worry about those “pics or it didn’t happen” naysayers. Pictures and videos of your experience are included.

Wreck Dive.  On this tour with Lost Reef Adventures, scuba divers get to explore two different shipwrecks in the area.  Tropical fish and turtles now call these ships home, and this is your chance to explore them.  With many shipwrecks in the area, they can choose the locations you’ll visit depending on your skill level.

Key West SNUBA Experience.  Time to get your SNUBA on!  This 3.5-hour experience introduces you to the SNUBA apparatus and gets you in the water, exploring the oceans depths.  The SNUBA allows you to breathe underwater, without scuba gear or certification.  You can be swimming with Ariel in no time.

Hydrobike Tour

What is a hydrobike, you ask?  It’s similar to a bicycle, except instead of wheels, it has large floaties on the sides.   I mean, who hasn’t wanted to ride a floating bicycle around Key West?  Now’s your chance!

Key West Hydrobikes. Travel the waterways of Key West at speeds around 4-6 mph powered by you. Book for an hour, two hours or half the day with their personal rentals options at our four locations in Key West. We love the options for Castaway Island…and the sunset tour with GLOW bikes! LIVE AVAILABILITY!

Mallory Square Sunset Hydrobike Tour.  If you want to take in the best sunset views Key West has to offer – Mallory Square is where it’s at.  And if you want to be the coolest person taking in the sunset views at Mallory Square, then it’s time for you to get on the Sunset Hydrobike Tour!  You’ll peddle across the water in your glowing hydrobike, while taking in the beauty all around you.  Best part?  You can stash drinks in the mini cooler.

Castaway Island Tour.  I think we can all agree that the real star of the movie “Castaway” was Wilson. This self-guided tour lets you take a hydrobike out to visit the most famous volleyball ever.  And after that, you can visit a nearby island for snorkeling or relaxing on the beach!  I promise you won’t get stranded.


I personally think parasailing is the most relaxing watersport activity there is.  It’s the perfect combination of adventure and peace.  Key West is amazingly beautiful, and I can’t imagine a more perfect place to fly above the ocean and take it all in.

Smathers Beach Parasailing Adventure.  Let’s fly! Enjoy the views of Key West and Smathers Beach from 300 feet up on this parasailing adventure.  No matter the age of the people in your group, parasailing is one of those watersports that is perfect for everyone!  Once you’re in the air, you can spot wildlife, and enjoy the peacefulness of being above the ocean.  Sunset Watersports has departures throughout the day, giving you excellent flexibility.

Parasailing Historic Harbor.  Guests will enjoy this parasailing tour above Key West and Historic Harbor.  You’ll be hoisted 300 feet in the air, so you’ll be able to take in all the amazing views surrounding the popular Historic Harbor area.

Key West Parasailing.  Can’t choose which friend to fly with?  This parasailing adventure not only offers tandem flights, but triple flights too, so you can enjoy the panoramic views around Key West with multiple friends!  You’ll board a state-of-the-art parasailing boat before being hoisted 300 feet into the air! Keep your eyes peeled for dolphins and experience a bird’s eye view of the beautiful Key West area.

Sunset Sails

Key West is famous for its sunsets and its beautiful waters.  Time to combine both of those and enjoy the sunset from the water.  Whether you’re looking for relaxation, or a party on the water, there’s a tour for you.

Sunset Sail Key West.  This is definitely the perfect end to an island day. Capture the magic of it all without being on a boat crowded with people. Sit back while the captain and mate raise the sails, shut off the engine and sail off into the sunset! You can even take the wheel.. or just take in the sights as you sail through a tour of Key West harbor, past the crowds at Mallory square and cross the line of the Gulf of Mexico to the Atlantic Ocean! LIVE AVAILABILITY.

Key West Sunset Dinner Cruise. Is there anything better than enjoying dinner and drinks while watching the sunset on a boat in the waters around Key West?  No! This Sunset Dinner Cruise offers a made-fresh-on-the-boat tropical buffet, a bar, a climate-controlled cabin, and dancing on the deck while you enjoy the sunset.  Perfection.

Seabreeze Sunset Harbor Cruise.  Enjoy sushi, snacks and drinks while traveling on this boat that journeys to unobstructed views where the Gulf meets the Atlantic.  You will cruise past the southernmost point while enjoying the sunset on this relaxing adventure.

Key West Sunset Cruise.  Complimentary beer and wine, a light-up dance floor, live music, a climate-controlled cabin, and watching the sunset on an amazing catamaran are the ingredients for a wonderfully memorable trip.

Wind and Wine Sunset Sail.  Live the high life by taking part in this 2-hour sunset sail around Key West!  On the Wind and Wine Sail, you’ll sample eight wines from around the world, along with five different beers and an array of appetizers.  Sounds amazing!

Private Luxury Sunset Cruise. Ready to take in the sunset on your own private yacht?  This cruise is for you!  This 4-hour sunset cruise allows you to enjoy the waters around the Lower Keys with just your small group.  Courage Charters allows you to bring your own picnic aboard, or they will cater one for you by request.

Key West Sunset Sail on America 2.0.  Sit back, sip champagne, and watch for dolphins aboard this fabulous ship!  This 2-hour excursion takes you out on the waters in search of the elusive “green flash.” Beer, wine, champagne, and hors d’oeuvres are included, and Bloody Marys can be purchased for an additional fee.

Sunset Catamaran Party Cruise. Enjoy margaritas, beer, wine, champagne, and appetizers aboard this party catamaran!  You’ll dance the night away while enjoying live music out at sea.

Glass-Bottom Boat Cruise and Reef Tour.  For something truly unique, try out this cruise on a magnificent glass-bottomed boat!  Get a sneak peek at the coral reefs that usually only scuba divers get to see, while aboard this climate-controlled vessel.

Dolphin Watch Tours

It’s a fact that dolphins are the best. (Fact!) Watching these amazing animals while you’re visiting the Keys is a must-do, and with several tours to choose from, you’ll be able to observe these animals in a way that is perfect for you.

Wild Dolphin Adventures. Your adventure is limited to six people – a much more personalized experience that won’t break the bank. Your Captain will determine what the group is most interested in, and consider the weather when planning the day’s tour.  LIVE AVAILABILITY.

Seabreeze Dolphin and Snorkel Tour. Take a cruise on Barefoot Billy’s catamaran and look for dolphins before snorkeling in the warm waters of Key West!  This tour is perfect for people of all ages in your group, and includes snacks and drinks.

Triple Combo: Sunset, Dolphin, Snorkel Tour.  This tour has it all!  Sunset sailing, looking for dolphins, and snorkeling too!  What more could you ask for?  This is the perfect evening adventure, and it includes complimentary beer and wine and live music.

Dolphin and Snorkel Cruise.  Hop aboard this catamaran and enjoy watching pods of bottlenose dolphins playing in the beautiful blue waters of Key West.  You’ll then explore the reef and observe tropical fish in their natural habitat.  Complimentary beer, soft drinks, and water is included.

Kayak Tours

Explore Key West in a whole new way with a kayak trip around the islands!  Explore the islands’ mangroves, observe marine wildlife, and get out in nature with one of these amazing kayak tours.

Private Clear Kayak Excursion. A wonderful way to get up close with marine wildlife is to take out a clear kayak – so that you can see all around (and underneath!) you.  A catamaran will take you and your party out to the backcountry of Key West, before you’ll set out to explore the mangroves and sandbars in the area.  A beautiful way to escape the crowds, and get to see nature from a unique perspective.

Clear Kayak and Snorkel. After exploring the marine wildlife from your clear kayak, hop out and get an even closer look by snorkeling while on this combo tour.  With a maximum of 6 people on each excursion, you’ll be able to truly escape and enjoy the peace that being out in nature can bring.

Guided Backcountry Paddle Tour.  This 2-hour tour lets you choose between a paddleboard or kayak before an experienced tour guide leads you through island mangroves.  You’ll glide across the calm waters around Key West while learning about the plants, animals, and wildlife.

Morning Sail, Snorkel, and Kayak Adventure. Get your day started off right with this morning sail, snorkel, and kayak excursion with Danger Charters. This half-day adventure includes observing wildlife from a 64-foot Schooner, kayaking through mangrove forests, and snorkeling in the tropical waters.

Snorkel Tours

We know Key West is beautiful from land, but what about what’s underneath?  Explore the coral reefs around Key West with a snorkel tour!  With so many different choices, you’re guaranteed to find an adventure that’s perfect for you.

Reef Dive or Snorkel Excursion. Both certified divers and beginning snorkelers will enjoy this adventure that takes you to two different reef locations. This 4-hour excursion takes small groups out to observe tropical fish, turtles, and coral.

Private Snorkel and Sunset Sail.  How does snorkeling and enjoying the sunset with just your closest friends sound?  If it sounds good to you, this is the perfect adventure for your group! Your small group will go out on a sailboat, before diving in for some of the best snorkeling you’ll ever experience.  Then relax while watching the sunset on your way back.

Sunset Sail, Snorkel, and Kayak. You can do it all with this sunset sail, snorkel, and kayak adventure.  This half-day adventure begins and ends on the sailboat, while you’ll do plenty of snorkeling and kayaking in the middle.  And ending the day watching the sunset off the coast of Key West sounds like perfection.

Dip and Sip Afternoon Snorkel.  Ready for some fun in the sun?  On the Dip and Sip Afternoon Snorkel you’ll head out on a new catamaran and get to the reef quickly and in style, so you can get right to snorkeling your afternoon away.  And did I mention there’s an open bar?  There is.  Sounds like way too much fun, but I think you can handle it.

Rise and Reef Snorkel Trip. Breakfast and snorkeling?  Yes, please!  Enjoy a light breakfast on Sunset Watersports’ newest catamaran before snorkeling in the blue waters of Key West.  Sounds like a great way to get your day started right.

Afternoon Reef & Ritas Tour. On this tour you’ll explore the coral reef in the afternoon, before relaxing on the deck of the catamaran with a frosty margarita in hand!  And if margaritas aren’t your thing, they also offer a morning excursion with complimentary beer and wine after your snorkel.

Sunset Rum Reggae Afternoon Snorkel.  After exploring the amazing coral reef, you’ll enjoy the sunset while relaxing on a spacious catamaran.  Sipping rum punch while listening to reggae music sounds like the perfect way to end a Key West day.

Half- and Full- Day Adventures: DO IT ALL!

With so many awesome adventures to experience in Key West – what if you can’t decide which ones to do?  Well, don’t you worry!  If you can’t decide what to pick – I say, PICK THEM ALL!  You will never suffer from FOMO with these choices, because you will be doing it all.

Venus Charters. Get a little taste of everything on this trip showcasing the best things to do out on the Key West water. If there is only one trip you are thinking of going on, or if you only have one day to experience the Florida outdoors, this is the trip, an absolute Key West must do. You’ll snorkel near coral heads and mangrove islands, light-tackle bottom fishing for snappers or grouper, and enjoy dolphin watching. Plan it out right, and you can even end the evening with a Key West sunset. LIVE AVAILABILITY.

Do-It-All Adventure. Have you ever wanted to do pretty much every single watersport offered in Key West in 6 hours?  Well, now’s your chance!  The Watersport Adventure pass offered by Sunset Watersports allows you unlimited access to 12 activities in a day.  Kayaking, jet skis, snorkeling, water trampolines, banana boat rides, kneeboarding, wind surfing, and even parasailing are all part of the deal.  And when you’re done? They’ll buy you a beer.

Beach Pass with Parasailing at Smathers Beach. Get unlimited access to everything Sunset Watersports offers on Smathers Beach with their Ultimate Beach Pass.  You’ll have 8 hours to experience activities like a parasail ride, a Hobie Cat sailboat excursion, volleyball, wind surfing, kayaks, rafts, paddle boards, and floats.

Full Day Sail, Snorkel, Kayak Excursion.  You’ll be able to take your time and experience sailing, snorkeling and kayaking to the fullest on this all-day excursion with Danger Charters.  A buffet lunch, drinks (including beer and wine), and light snacks are included on this 6.5-hour adventure.

Sail, Kayak, and Snorkel Half-Day Eco Tour.  Escape the crowds and experience what Key West is truly about with this 4-hour tour.  You’ll enjoy a sailing adventure on a catamaran, observe marine wildlife while snorkeling, and kayak through mangrove forests on this trip.  Light snacks are included, or you can bring a picnic lunch to enjoy.

Private Harbor Day Sail.  This 1.5-hour sightseeing cruise is a truly unique way to learn all about Key West. You can relax with a drink while learning all about the history of the area, and you’ll even get a chance to sail yourself!

Private Chill Out Lily Pad Sail.  Escape the craziness and chill with your friends on this relaxing excursion.  A max of 6 people will head out on a sailboat before it drops anchor and lets you and your group relax on a giant, floating lily pad in the ocean.

Private Clear Kayak, Snorkel, Boat Cruise.  A private cruise and activities for just your group?  Yes!  If it’s getting too people-y in Key West for you, this private sunset boat cruise also includes snorkeling and a trip exploring the mangroves in a clear kayak.

Private Luxury Day Cruise. Skip those smaller boat rentals. You’ll be able to customize your day at sea aboard a luxury yacht on this 4-hour cruise that explores the islands in the Lower Keys.  Whether you want to explore a secluded island, or observe dolphins in their natural habitat, you are guaranteed to have a memorable experience.  You can also bring a picnic or have one catered for you as you glide across the blue waters.

Key West Full Day Tour From Miami Beach. While you’re in Miami, take a day to explore Key West!  This tour starts with them picking you up from your Miami hotel and taking you across the famous Overseas Highway 1.  Once there, you’ll have five hours to explore the city on your own.  Or you can book a 2-hour tour on a glass-bottom boat, or a 2.5-hour excursion to see dolphins and snorkel.  Whatever you’re ready for, this is one day trip you won’t soon forget.

Key West Ultimate Express Water Adventure.  For those who want to experience all the watersports in half a day – this adventure is for you! The Ultimate Express Water Adventure allows you to experience many different water sports in 3.5 hours.  You’ll parasail, go on a short jet ski tour, ride on a banana boat, and swim and play on giant water toys.  Then maybe consider taking a nap.

Pin This Post

Disclosure: 365 Atlanta Traveler is a Visit Florida Digital Marketing Program Partner. This post contains affiliate links at no cost to you.

Kate Gelsthorpe is a former TV news writer, and a born and raised Georgia girl who grew up camping with her family at state parks around central and south Georgia. After 18 years in Atlanta, her family recently moved to Athens, and in their spare time you can find them exploring their new hometown. She and her husband, Kevin, are the proud parents of an 8-year-old dinosaur expert, and a 6-year-old outdoor-loving fashionista.

Be the first to comment on "The Key West Watersports Tours You Shouldn’t Skip"

Leave a comment

Your email address will not be published.