Key West Extreme Activities, Tours & Attractions

Parasail the ocean blue skies of Key West where you’ll get a bird's eye view of Key West and Smathers Beach from 300 feet up in the sky! Fly high, have the time of your life, and float like an eagle on the wind. Take in the scenery, look out for marine wildlife, or simply enjoy the ocean air as you soar. So what are you waiting for?! Spread your wings and get ready for liftoff. Book your experience today!

Take a thrilling ride around the beautiful Key West by jet ski. Zip through the emerald waters and forget about your worries. See different sites such as, the Southernmost Point, Key West Harbor, and a local sandbar where you will have a chance to take a dip. While on the water, you may even catch a glimpse of bottlenose dolphins, pelicans, and many more marine animals in their natural habitats. Don't miss your bragging rights, book this thrilling Jet Ski Tour today!

Don't miss your chance to “Do it All” with a day-long Watersport Adventure Package in Key West. This all-inclusive experience gives you full access to a variety of awesome activities like kayaks, paddleboards, snorkeling, jet skis, floatables, water trampolines, and banana boat rides. Choose your activities and have your day your way with this Do It All Water Sports Adventure Package. Book today!

Embark on a spectacular sunset sailing adventure off the coast of Key West, Florida in search of the famed "Green Flash." Experience the magic and romance of sailing at dusk as you sip champagne and watch for dolphins and other marine wildlife in the surf. Your friendly captain and crew will teach you the basics of sailing and even let you take the wheel. So, take a turn at the helm of one of the fastest schooners in the United States, book today!

Get out on the water and enjoy Key West's newest and most luxurious party boat. FishMonster Max Half-Day Party Boat Fishing is your chance to fish the reef like never before. Cruise on this completely remodeled 64-foot twin engine catamaran, relax in the cool air-conditioned galley, or head up top for incredible 360 degree views of the ocean. Take your fish home to be enjoyed later or walk them over to any one of the numerous restaurants located along the dock and have it cooked just the way you like it! Spend your morning fishing and your evening enjoying your fresh caught dinner. This is the fishing trip of a lifetime, book today!

Explore beautiful Key West as you circumnavigate its tropical waters on this Jet Ski Tour. This exciting adventure travels over 27 miles of Caribbean water. Bask in the sun and and learn interesting facts about Key West as you take in its breathtaking beauty from your personal watercraft. You'll find the best way to see Key West is on a Jet Ski tour, conveniently departing from the Reach Resort! Reserve your spot today!

Head out on the water for a fishing adventure you will never forget! This party boat fishing charter offers a premium fishing excursion for anglers of all skill levels. Let the experienced captain and crew take you to their tried-and-true fishing spots across the aquamarine South Florida waters. Limited to 10 passengers, this fun, inshore expedition is a great way to introduce family and friends to a new sport, get the kids out on the water, or simply add an exciting Key West fishing experience to your island visit. Arguably the #1 most revered fishing destination in the world, the Florida Keys is the perfect place to plan a fishing trip. So don't miss the boat, book your spot today!

Treat yourself to an action-packed, 28-mile Jet Ski tour among the sparkling waters of Key West and beyond. Join entertaining and experienced guides as they lead you on a scenic tour around the island that includes a slew of fantastic sights like the Southern Most Point, Key West Harbor and a local sandbar where you’ll have a chance to take a dip! Choose the last trip of the day and take in the beautiful sunset! Don't miss out on this fast-paced adventure, book yours today.

Treat yourself to an evening of incredible snorkeling, delicious drinks, and groovy melodies on the Miss Valyn Catamaran. A twilight experience unlike any other, this is your opportunity to enjoy the nightlife while having the option to plunge into the depths by Florida's best reef! Take in the fleeting Key West sunset while indulging in an ambiance that only the cat delivers. Enjoy reef snorkeling, draft beer & wine on this snorkeling experience. Book your spot today!

Are you looking for the best kept secret in Key West?! If so, then hop in your own personal, mini speedboat and follow your knowledgeable guide into Key West's backcountry. You'll race through lush mangrove islands and see amazing marine wildlife along the way while boating in Key West's magical tropical waters. Book today and set out on an amazing adventure on the water with this Key West Safari Eco Tour!

Don't miss your chance to “Do it All” with a daylong Watersport Adventure Package with Parasailing in Key West. This all-inclusive experience gives you full access to a variety of awesome activities like kayaks, paddleboards, snorkeling, jet skis, floatables, water trampolines, and banana boat rides. Choose your activities and have your day, your way with this Do It All Water Sports Adventure Package with Parasailing. Book today!

Rise, shine, and hop aboard this Rum Runner Downtown Morning Cruise. Relax and start your day the right way as you sightsee, take photos, and search for marine life on this easy going morning cruise. Enjoy a worry free experience with your USCG licensed captain. Listen to stories of yesteryears and learn a little about Key West's colorful history. Don't miss this one, book your Rum Runner Morning adventure today!

Soar above an island paradise on a tropical breeze with a Key West Parasailing Adventure. Enjoy miles of breathtaking scenery and panoramic views as you rise above the clear water and spot dolphins, tropical fish, and more! Share this grand experience with 1, or even 2, of your favorite people as you experience the breathtaking views and thrilling ocean dips together! Venture out on a Key West Parasailing Adventure today for an extraordinary bird's-eye view of paradise! Book now!

Cruise the gorgeous water on the best value bar boat in Key West and give a cheers for every gorgeous sight. Perfect for you and up to 5 of your crew to kick back and chill or snorkel and swim at the stop at Wisteria Beach. See Sunset Key, Wisteria Island, a 100 year old shipwreck, and more. You can BYOB or grab drinks at the beach bar before at a discounted rate, so don't miss the boat! Book your Rum Runner Bar Boat Early Bird Cruise today!

Have you ever wanted to take the wheel or hoist the sails of a real schooner? If so, here's your chance! This half-day Bugeye Backcountry Tour is an amazing mix of sailing, snorkeling, and kayaking among the most scenic settings in the Florida Keys, including the Sponge Garden Reef and Mangrove Island. Discover the amazingly diverse ecosystem of Key West’s backcountry and observe the abundant wildlife from the water. This tour is a MUST for outdoor enthusiasts! Book your spot today!

If you are looking for something exciting to do over downtown Key West, then this is the adventure for you. Parasail the blue skies over Key West's eclectic and colorful downtown and see everything from 300 feet in the air! One of the most extreme and stunning activities around, so take in the scenery, look below for mesmerizing marine wildlife, or simply enjoy the salty ocean air as you soar. So what are you waiting for? Book today!

Enjoy everything Smathers Beach has to offer with this Beach Pass Watersports Package with Parasailing. Capture the magic of Smathers Beach with this all-day Ultimate Beach Pass. Jump on a paddleboard, kayak or hobie cat and explore the coast. Cruise through the crystal clear waters as you explore the largest beach in Key West. This pass includes your choice of a parasailing ride or chair & umbrella. A tremendous value and a great idea for groups, get your Beach Pass and get out on the water today!

Enjoy everything Smathers Beach has to offer with this Beach Pass Watersports Package with Beach Chairs and Umbrella. Capture the magic of Smathers Beach with this all-day Ultimate Beach Pass. This amazing pass offers something for everyone and includes volleyball, paddleboard, windsurfing, kayaking, Hobie Cat Sailboat, beach chair rentals, umbrella rentals, and float rentals. A tremendous value and a great idea for groups, get your Beach Pass and get out on the water today!

What better way to spend your day than with a shared sandbar experience? Travel the crystal clear water of Key West, Florida with family and friends to the backcountry sandbars of Key West. Feel the sun and the salty breeze on your skin. Take a moment and admire the natural beauty this part of Florida has to offer. Your captain knows the best spots to make your experience one to remember. Once at the sandbar, get out in the water! Relax on floats while the water gently rocks you or dive under the water as you snorkel. Make lifelong memories, book your Shared Sandbar Experience today!