Key West Extreme Activities, Tours & Attractions

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Jun 18 - Jun 24
Parasailing-Smathers-Beach-by-Sunset-Watersports

Smathers Beach Parasailing Adventure

37 ratings
1 Hr.
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!
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Jet-Ski-Island-Tour-from-Parrot-Key

Jet Ski Island Tour from Parrot Key

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1.5 Hrs.
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!
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Do-It-All-Adventure-by-Sunset-Watersports

Do It All Water Sports Adventure Package

45 ratings
6 Hrs.
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!
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Key-West-Sunset-Sail-on-America-2-0-by-Classic-Harbor-Line

Key West Sunset Sail on America 2.0

45 ratings
2 Hrs.
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!
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FishMonster-Max-Half-Day-Party-Boat-Fishing

FishMonster Max Half-Day Party Boat Fishing

8 ratings
5 Hrs.
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!
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Booked 2 times in last 48 hrs
Barefoot-Billy-s-Jet-Ski-Tour-of-Key-West-from-the-reach-resort

Jet Ski Tour of Key West from The Reach Resort

2 ratings
90 Min.
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!
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Key-West-Premium-Head-Boat-Fishing-Experience

Key West Premium Head Boat Fishing Experience

11 ratings
4 Hrs.
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!
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Jet-Ski-Island-Tour-by-Sunset-Watersports

Jet Ski Island Tour of Key West from Cow Key Marina

30 ratings
2 Hrs.
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.
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Sunset-Snorkel-Sip-and-Sail-Cruise-with-Live-Music-by-Sunset-Watersports

Key West Sunset Snorkel Cruise

60 ratings
3 Hrs.
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!
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Island-Hopper-Excursion-with-Snorkel-by-Sunset-Watersports

Key West Safari Eco Tour

12 ratings
2.5 Hrs.
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!
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Island-Ting-Kayak-and-Snorkel-Tour-by-Sebago-Watersports

Key West Sailing, Kayak, & Dolphin Watching with Breakfast and Lunch

10 ratings
6 Hrs.
This fun-filled Key West tour combines three awesome adventures into one package. Enjoy a day of sailing, snorkeling, and a grand kayak tour through the mysterious mangrove backcountry. An awe-inspiring eco-tour of glorious Key West, you'll embrace nature in all of her glory as you encounter and observe diverse wildlife on land and under the sea. This all-day adventure includes delicious spreads for both breakfast and lunch, as well as an afternoon snack that is sure to please. Book your Key West adventure today!
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Key-West-Sandbar-Snorkeling-and-Island-Hopping

Private Key West Sandbar & Snorkeling Charter

9 ratings
4 Hrs.
Experience the beautiful Florida Keys and its lush mangroves, islands, turquoise waters, and marine life on this Private Key West Sandbar & Snorkeling Charter for up to 6 guests. Skip the usual trips with salty sailors and opt for a day with the nicest captain around. Cruise on a center console and snorkel and chill on a sandbar or opt for some island hopping fun, your trip is totally customizable. Don't miss out, book yours now!
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Private-Sandbar-Experience

Private Sandbar Experience

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2 - 4 Hrs.
There's no better way to spend your day than with this Private Sandbar Experience. Travel the crystal clear water of Key West with family and friends to the backcountry sandbars. Feel the sun and the salty breeze on your skin. Take in the 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 to splash and play! Swim, relax on floats, or dive down under the water and snorkel. Make lifelong memories, book this experience now!
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Rum-Runner-Bar-Boat-Castaway-Cruise

Rum Runner Bar Boat Castaway Cruise

9 ratings
4 Hrs.
Enjoy this Rum Runner Bar Boat Castaway Cruise and get out on the water for some fun to last the summer through. 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 and/or sample rum on board. So, don't miss the boat! Book your spot today!
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Beach Pass Watersports Package with Beach Chairs and Umbrella

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8 Hrs.
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!
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Rum-Runner-Sunset-Downtown-Tour

Rum Runner Sunset Downtown Tour

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1.5 Hrs.
Enjoy a sunset cruise on the best value bar boat in Key West. Cruise the gorgeous water on this Rum Runner Bar Boat and give a cheer for every gorgeous sight. Perfect for you and up to 15 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 at a discounted rate, this trip is a perfect way to end your day. So, don't miss the boat! Book your Rum Runner Sunset Downtown Tour now!
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Rum-Runner-Downtown-Morning-Cruise

Rum Runner Downtown Morning Cruise

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1 Hr.
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!
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Do-It-All-Water-Sports-Adventure-Package-with-Parasailing

Do It All Water Sports Adventure Package with Parasailing

6 ratings
6 Hrs.
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!
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Beach-Pass-Watersports-Package-with-Parasailing

Beach Pass Watersports Package with Parasailing

1 rating
8 Hrs.
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!
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Private-Key-West-Dolphin-Sightseeing-Charter

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