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Key West - Outdoor Activities

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Ranked #1 of 137 Outdoor Activities in Key West
Category: Gear rentals; Outdoor Activities
Owner description: Enjoy a fun filled day in the Florida Keys. Spend a few hours sportfishing or family fun fishing. Plan a beach excursion,... more » Owner description: Enjoy a fun filled day in the Florida Keys. Spend a few hours sportfishing or family fun fishing. Plan a beach excursion, swimming, snorkeling, sight seeing,or a sunset cruise. See the annual powerboat races from the water. Design your day on the water with Captain Ron on the Blue Eyed Trader. « less
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Ranked #2 of 137 Outdoor Activities in Key West
Category: Water sports
Owner description: Stand up Paddleboard Eco-tours and lessons. Paddle through the amazing waters of Key West as well as the Magical Mangrove... more » Owner description: Stand up Paddleboard Eco-tours and lessons. Paddle through the amazing waters of Key West as well as the Magical Mangrove Forest!! Experience the water in a way unlike any other!! Learn about the environment and eco-system that surrounds our island!! Come enjoy our the Florida Keys with SUP Key West « less
Map | Visitor photos (69)
Ranked #3 of 137 Outdoor Activities in Key West
Category: Water sports
Owner description: Treat yourself to a one of a kind fishing experience in Key West Florida. High Stakes Charters offers a 53' Striker... more » Owner description: Treat yourself to a one of a kind fishing experience in Key West Florida. High Stakes Charters offers a 53' Striker Sportfishing vessel. A/C, twin engines, tournament grade tackle, 2 staterooms, 2 bathrooms, full service galley and a spacious lounge area with leather couches. High Stakes is located at Oceanside Marina which is on the south side of the island. This means we are closer to the fishing grounds allowing you more time fishing the beautiful crystal clear blue water of the Gulf Stream. Our professional crew with 35 years combined fishing experience work extremely hard to catch Blue Marlin, Sailfish, Wahoo, Mahi Mahi, Black fin Tuna, Yellowtail Snapper, Grouper, a vast variety of sharks and much, much more. « less
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Ranked #4 of 137 Outdoor Activities in Key West
Category: Dolphin & whale watching
Owner description: Located at the Historic Seaport in the heart of Old Town Key West, Dolphin Watch is Key West's original wild dolphin... more » Owner description: Located at the Historic Seaport in the heart of Old Town Key West, Dolphin Watch is Key West's original wild dolphin charter... ...Climb aboard Key West's original Dolphin Watch and for the next four hours, you'll come to realize why we've been consistently running the island's most enjoyable and successful tour of its kind since 1986! And while nearly 30 years of service is something few Key West activities -- land or sea-based -- can boast, it's really our trusty boat and dedicated crew that set this voyage apart. With the largest boat in its class, our six passenger maximum means loads of space for you to walk about, catch some rays, hide out in the shade, or even escape a passing rain shower inside our cozy cabin. Many passengers enjoy simply relaxing on the way to watch dolphins or while we cruise to our secluded snorkeling spot, while others are interested in the journey. If that's you, then hop up top and chat up our captain, who'll be delighted to point out wildlife, landmarks and other local knowledge concerning Key West's pristine marine ecosystems. « less
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Ranked #5 of 137 Outdoor Activities in Key West
Category: Other outdoor activities; Outdoor Activities
Owner description: Get out on the waters of Key West in comfort and privacy. Our deck boats are extremely comfortable and equipped with... more » Owner description: Get out on the waters of Key West in comfort and privacy. Our deck boats are extremely comfortable and equipped with everything needed; snorkel gear, fishing rods, stereo, toilet, freshwater rinse down, shade canopy, and grill. Some of the trips we offer are snorkeling, sandbar trips, fishing, lobstering, spearfishing, dolphin watches, sunset/booze cruises, island hopping, and more. Boats are also available for rental. Give us a call with any questions! « less
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Ranked #6 of 137 Outdoor Activities in Key West
Category: Other outdoor activities; Outdoor Activities
Owner description: Enjoy a relaxing day exploring the beautiful waters surrounding Key West aboard a comfort-driven 23ft Hurricane Deck Boat.... more » Owner description: Enjoy a relaxing day exploring the beautiful waters surrounding Key West aboard a comfort-driven 23ft Hurricane Deck Boat. The day is entirely yours! You can snorkel patch reefs, cruise to secluded islands, fish for snappers etc., watch for dolphins, sea turtles, stingrays...and/or just float on your own white sand bar. Discover the true beauty of the Keys, & have a day you will always remember « less
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Ranked #7 of 137 Outdoor Activities in Key West
Category: Bike tours
Owner description: Upon arriving at the bike shop, you'll be fitted with your bicycle and begin your approximately three-hour pedal through... more » Owner description: Upon arriving at the bike shop, you'll be fitted with your bicycle and begin your approximately three-hour pedal through town. You will see the highlights of Key West, of which there are many. Pass Simonton Street Beach, the Green Parrot Bar, Key West Cemetery, Higgs Beach and the Southernmost Point of the United States, just 90 miles north of Cuba. Of particular note is the Customs House, which presides over historic Mallory Square. Dating to 1891, the faithfully restored, four-story architectural gem was originally home to the island's customs office, postal service and district courts. "Old 91" is today a national landmark and headquarters of the Key West Art & Historical Society. Another slice of local history unfolds as you approach the Presidential Gates of the Harry S. Truman Little White House. Built in 1890 as the first officer's quarters on the submarine base naval station, the abode served as Harry S. Truman's base of presidential operations during his 11 visits to Key West. Of course, Key West also is known as the home of Ernest Hemingway. During your bike ride, you will see the residence located at 907 Whitehead Street, across from the Key West lighthouse, where the famed writer lived from 1931 to 1939. One of Hemingway's legendary haunts was Sloppy Joe's Bar. Founded in 1933, the bar was located on Greene Street, just off Duval Street, during Hemingway's day. The bar has since moved to its current location on Duval Street, taking with it its storied connections to Hemingway, who suggested the name for the establishment. Other landmarks on today's roster include Dog Beach, Flagler Train Depot, Jimmy Buffet's first house, and Jimmy Buffet's Margaritaville, the Duval Street watering hole that embodies the laid-back lyrics of the beloved singer/songwriter. After returning to the bike shop you will finish with a slice of Key Lime pie, a refreshing must-taste here in Key West. « less
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Ranked #8 of 137 Outdoor Activities in Key West
Category: Sports Camps/ Clinics; Water sports
Owner description: At Sunrise Kiteboarding we focus on the quality of your experience instead of a quantity of customers. Whether you are an... more » Owner description: At Sunrise Kiteboarding we focus on the quality of your experience instead of a quantity of customers. Whether you are an avid sportsman looking to try the great sport of Kiteboarding, or a group looking for an all around great day, We are here for you. Our goal is to serve you in a way no other outfitter will. From the incredible food cooked on our grill, private secluded islands or great watersports, its all about the over all experience. Our ultimate goal for our clients is to have them say "that was the best day ever!!" « less
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Book a Tour
$49* and up
Ranked #9 of 137 Outdoor Activities in Key West
Category: Water sports
Owner description: For over 24 years we are Key West's premier boat tour and water sports operator. Our fleet of sailing catamarans, parasail... more » Owner description: For over 24 years we are Key West's premier boat tour and water sports operator. Our fleet of sailing catamarans, parasail vessels, and schooners offer a wide variety of tours and private excursions that are also an excellent value. We invented and perfected the tours that others seek to imitate. Get the best price for Key West's #1 tours when you book online. « less
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Ranked #10 of 137 Outdoor Activities in Key West
Category: Kayaking & canoeing
Owner description: If you want to get off the beaten path with Kayak Kings.... then please join us for one of our AMAZING tours. From our... more » Owner description: If you want to get off the beaten path with Kayak Kings.... then please join us for one of our AMAZING tours. From our mangrove maze tour to an kayak/snorkel tour, to a full day of exploring our back country and beautiful sand bars. We always look for dolphins on are way back and almost always see them and turtles. We also offer kayak fishing...so let us capture a picture of you with the big one. All of our back country and snorkeling reefs and shipwrecks are tide/weather dependent. So please call and get the best time to go get off the beaten path! « less
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Ranked #11 of 137 Outdoor Activities in Key West
Category: Eco tours
Owner description: We offer a variety of options to explore and experience the natural wonders of the Florida Keys. World class birdwatching,... more » Owner description: We offer a variety of options to explore and experience the natural wonders of the Florida Keys. World class birdwatching, lush mangroves, coral & sponge gardens teeming with marine life. We offer guided eco tours, downwind kayak trails(easy paddling),paddleboard and kayak rentals, an all inclusive sail, kayak, snorkel charter, and evening sails. We cater to small groups which provide personalized service, we have a courtesy shuttle, we are The Best that there is to offer, with knowledgeable guides with over 15 years of experience in Key West. We are an owner/operator buisness. « less
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Ranked #12 of 137 Outdoor Activities in Key West
Category: Fishing charters & tours

If you're looking for a private charter with a top notch captain, Far Out Charters is right for you. Captain Chris Mendola will customize the trip a of a lifetime for you. From... more »

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Ranked #13 of 137 Outdoor Activities in Key West
Category: Gear rentals; Outdoor Activities
Owner description: We offer a fun & exciting way to enjoy seeing the sights in Key West for people with temporary or permanent mobility issues.... more » Owner description: We offer a fun & exciting way to enjoy seeing the sights in Key West for people with temporary or permanent mobility issues. We rent top quality & reliable Pride Mobility Scooters, Electric Wheelchairs & Manual Wheelchairs to enjoy what you want to see at your own leisure. We also have Fun Colorful Bicycles available for rent, all equipped with Baskets, Lights, Locks, & Koozies « less
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Ranked #14 of 137 Outdoor Activities in Key West
Category: Tours; Water sports
Owner description: 2 hour guided kayak tour, 4 hour guide kayak/snorkel tour, kayak rentals, stand up paddleboard rentals. Complimentary Shuttle... more » Owner description: 2 hour guided kayak tour, 4 hour guide kayak/snorkel tour, kayak rentals, stand up paddleboard rentals. Complimentary Shuttle available for tours!Our 2 hour tour explores the shallow, calm waters and mangrove habitats between Key West and Stock Island. Beginners welcome!!the 4 hour tour explores more remote back country areas and includes snorkeling.Kayak rentals available with map of the area included.No waves? No problem. Stand up paddleboarding is great fun!!!! « less
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Ranked #15 of 137 Outdoor Activities in Key West
Category: Fishing charters & tours
Map | Visitor photos (106)
Ranked #16 of 137 Outdoor Activities in Key West
Category: Fishing charters & tours
Map | Visitor photos (122)
Ranked #17 of 137 Outdoor Activities in Key West
Category: Water sports
Owner description: Over 41 years ago, Capt. Billy Wickers III followed in his grandfather's and father's footsteps. Now Billy is a 4th... more » Owner description: Over 41 years ago, Capt. Billy Wickers III followed in his grandfather's and father's footsteps. Now Billy is a 4th generation captain. Captain Billy grew up working in the family charter business, working as a mate for his dad, and got his captain's license at the young age of 18 in 1990. He captained his dad's boats, Linda D III and IV, and was able to buy his own boat the Linda D V in 2003 which he owns and operates. Captain Billy has been recognized for his fishing abilities by winning numerous awards since 1990 to present , including the prestigious Key West Fishing Tournament's Outstanding Guide Award, most releases in general division, and also most Sailfish and Marlin releases, which he has won for 5 consecutive years. He s been recognize as captain of the moth by Gray taxidermy..Also Linda D IV & V have been Awarded for the 2012 BEST OF KEY WEST AWARDS IN THE CHARTER BOATS Category by the Key West Award Promgram Committee. Capt. Billy Wickers III will definitely make your fishing trip a memorable event for you and your family. « less
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Ranked #18 of 137 Outdoor Activities in Key West
Category: Fishing charters & tours
Owner description: Key West fishing charters guided by a mostly inshore charter boat company that offers flats fishing, backcountry fishing, and... more » Owner description: Key West fishing charters guided by a mostly inshore charter boat company that offers flats fishing, backcountry fishing, and light tackle wreck and reef style fishing. Captain Kyle Kelso will take you on an exciting adventure to areas off of the Lower Keys, Key West, or Marquesas Keys that you will be sure to remember. Capt. Kyle only uses top of the line fishing equipment and has a brand new boat. « less
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Ranked #19 of 137 Outdoor Activities in Key West
Category: Other outdoor activities; Outdoor Activities
Owner description: Offering Kiteboarding lessons and rider trips, Stand-up paddle-boarding trips -- all by boat to nearby locations in the... more » Owner description: Offering Kiteboarding lessons and rider trips, Stand-up paddle-boarding trips -- all by boat to nearby locations in the national Marine Sanctuary. All gear included. « less
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Ranked #20 of 137 Outdoor Activities in Key West
Category: Other outdoor activities; Outdoor Activities
Owner description: Being in Key West is fine, but let’s get on the water! Here at Laid Back Key West, charters are customized to fit your needs.... more » Owner description: Being in Key West is fine, but let’s get on the water! Here at Laid Back Key West, charters are customized to fit your needs. Instead of having to choose one type of charter (such as fishing or snorkeling) we allow you to create a package deal so you can do exactly what you want, without having to rush due to time restrictions. We want to give you and your family an experience to remember! « less
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Ranked #21 of 137 Outdoor Activities in Key West
Category: Parasailing & paragliding
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Book a Tour
$46* and up
Ranked #22 of 137 Outdoor Activities in Key West
Category: Water sports

Fury Water Adventures is located in the magnificent island paradise of Key West, Florida and has been in business for over three decades in the “Southernmost” city.  Aboard Fury's... more »

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Ranked #23 of 137 Outdoor Activities in Key West
Category: Eco tours
Owner description: Nomadic SUP is the premier Stand Up Paddleboard tour company in Key West and the lower Florida Keys. We specialize in Eco... more » Owner description: Nomadic SUP is the premier Stand Up Paddleboard tour company in Key West and the lower Florida Keys. We specialize in Eco Tours which are both fun and informative. Our tours include transportation, snacks, water and professional instruction that ensures new and experienced paddlers will both have fun and safely be able to enjoy the sport of SUP in the pristine eco systems surrounding Key West. « less
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Ranked #24 of 137 Outdoor Activities in Key West
Category: Water sports
Owner description: Adventure Watersport Charters, specializes in daily and overnight liveaboard scuba diving, spear fishing and deep sea fishing... more » Owner description: Adventure Watersport Charters, specializes in daily and overnight liveaboard scuba diving, spear fishing and deep sea fishing charters from Key West to the Marquesas Keys, Dry Tortugas National Park and all points in between at land or sea. So whether you're an avid fisherman looking for the ultimate overnight fishing trip adventure, a SCUBA diver wanting to exploring the exotic underwater world of the Keys reefs & wrecks, or a family looking for a serene peaceful & leisurely way of reuniting your family from the hectic fast track of life, Adventure Watersport Charters is your ultimate destination where adventure exceeds imagination. « less
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Ranked #25 of 137 Outdoor Activities in Key West
Category: Other outdoor activities; Outdoor Activities
Owner description: Light Tackle Sportfishing. Charter fishing trips, reef fishing, offshore fishing. Snapper, Grouper,Tarpon, Sharks, Sailfish,... more » Owner description: Light Tackle Sportfishing. Charter fishing trips, reef fishing, offshore fishing. Snapper, Grouper,Tarpon, Sharks, Sailfish, Tuna, Mahi Mahi, Wahoo, Swordfish and Marlin. « less
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Ranked #26 of 137 Outdoor Activities in Key West
Category: Fishing charters & tours
Owner description: Ocean Energy Charters is Key West's most memorable fishing experience. She is a 40 ft. Custom Sport Fisherman with twin... more » Owner description: Ocean Energy Charters is Key West's most memorable fishing experience. She is a 40 ft. Custom Sport Fisherman with twin turbo-diesel engines, whose captain and crew are SERIOUS about fishing. We offer all sorts of trips including Reef, Wreck, Offshore, and Swordfishing trips. Come fishing aboard the Ocean Energy it is an experience you will NEVER forget. « less
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Ranked #27 of 137 Outdoor Activities in Key West
Category: Gear rentals; Outdoor Activities
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Ranked #28 of 137 Outdoor Activities in Key West
Category: Other outdoor activities; Outdoor Activities
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Ranked #29 of 137 Outdoor Activities in Key West
Category: Scuba & snorkelling
Scuba diving for the beginners and advanced alike, featuring dives to coral reefs and WWII wrecks.
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Ranked #30 of 137 Outdoor Activities in Key West
Category: Water sports
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Trusted travel advice about Key West