Watersports and Kayaking

The Florida Keys are known as the Pearl of the Caribbean. It’s a long strand of islands surrounded by water on all sides. If you ‘re visiting the islands for the first time, make sure you plan on spending some time on the water. The true wonder and grandeur lies off-island. And, there are so many ways to experience it. You can experience the splendor and adventure of sailing on a Tall Ship in Key West, or take a fairy to the wilds of the Dry Tortugas (also out of Key West).  You can explore the wonders of the Florida reefs by taking the  glass-bottom boat tour out of Pennekamp park in Key Largo, or see the glorious reef first-hand via a snorkeling trip. You can also kayak or paddle-board the tranquil waters of the Back-Country. Regardless of the method you choose to experience the waters… you will find it awe-inspiring.

Key Largo

If you are visiting the keys – it’s all about getting out on the water, and there are lots of options. Families with smaller children can book a trip on the glass bottom boat at John Pennekamp Park. Kayaking, paddle-boarding or jet-skiing are great options for the more adventurous. 

Key Largo Princess Glass Bottom Boat
Daily 2-hour tours departing from John Pennekamp Coral Reef State Park. View the underwater world of the Key Largo National Marine Sanctuary. This is an excellent way to experience the ocean for families with young children or folks unaccustomed to boating, fishing and swimming.
99701 Overseas Highway
Key Largo, Florida 33037
(786) 749 – 9033
www.keylargoprincess.com

Garl’s Coastal Kayaking
Kayak the Everglades with knowledgeable guides that know the Everglades and backcountry as if it were their own backyard. Experience the wonder of this wilderness with guides and naturalists. This is a must-see for outdoor enthusiasts. You’ll definitely want to check this off your bucket list.
99010 Overseas Hwy
Key Largo, FL 33037
(305) 393-3223
www.garlscoastalkayaking.com

Caribbean Water Sports And Excursions
Located at the Key Largo Hilton, Caribbean Water Sports offers activities including Jet ski and Wave runner rentals, parasailing, enviro-tours and  eco-tours. They also offer sailing tours to Everglades National Park, snorkeling tours of the coral reefs of Pennekamp State Park and the Florida Keys National Marine Sanctuary, and Sunset Cruises on Florida Bay.
97000 S Overseas Hwy
Key Largo, FL 33037 (305) 852-4707
www.caribbeanwatersports.com

Tropic Water Sports
Located at mile marker 94.5, next to Snappers Oceanfront restaurant, Tropics water sports offers paddle-board, raft, kayak, clear kayak and jet-ski rentals, plus snorkeling and eco-tours. Explore the out-lying mangrove islands, Dove and Rodriquez Keys and Dove Creek. Guests can expect to see wading birds, dolphins, manatees and more.
139 Seaside Ave
Key Largo, FL 33037 (305) 709-9898
www.tropicwatersports.com

Action Watersports
A great place to rent jet-skis and get out on the waters surrounding key largo.
107690 Overseas Hwy
Key Largo, FL 33037
(305) 998-8190
www.jetskikeylargo.com

Sunshine Water Sports
Located at Gilbert’s resort at the entrance to the keys. Sunshine Water Sports rents jet-skis, kayaks stand-up paddle boards and jet-boats.  Explore beautiful Jewfish Creek and Blackwater sound. See mangroves, great blue herons, dolphins, manatees  and more.
107900 Overseas Hwy
Gilberts Resort
Key Largo, FL 33037
(305) 440-9954
www.sunshinewatersports.com

Tiki Watersports
Kayak and Sailboat rentals.
94381 Overseas Hwy
Tavernier, FL 33070
(305) 852-9298
www.tikiwatersports.com

Keys Adventures Water Sports
Located at the famous Jimmy Johnson’s Big Chill Grill. Take part in para-sailing, or rent paddle boards, kayaks jet-skis or even jet-packs! They also offer eco-tours and sunset cruises. Explore the surrounding waters, then return to the Big Chill and enjoy the pool, restaurant and JJ’S sports bar.
104000 Overseas Hwy
Key Largo, FL 33037
(305) 731-9472
www.keysadventureswatersports.com

Tavernier/Islamorada

Tavernier and Islamorada have some of the largest and best Watersports Outfitters. Several offer boat rentals, that come complete with snorkeling and fishing equipment. Some outfitters offer eco-tours. You can also rent Hobie Cats or Sunfish sailboats. Almost all the major resorts rent jet-skis, kayaks and stand-up paddle-boards.

AquaBlue Adventures
Located at the Marker 88 restaurant, Aquablue offers full-day, half-day and 3 hour boating trips for up to 6 passengers as well as 2 hour sunset or eco-tours. The tours explore the waters surrounding Islamorada and include snorkeling equipment, fishing equipment, 2 Stand-up paddleboards, rafts, lounge chairs, footballs, frisbees, digital photography, and lunch.
Islamorada, Florida 33036
(305) 900–7350
www.aquaadventures.com

Island Boat Rentals
Offering hourly, 1/2 day, daily, weekly and monthly boat rentals. They have a wide variety of boats to choose from. The boats are equipped with bimini tops to provide shade during your boating adventure, swim & dive ladders, gps, depth finders, rod & cup holders, live bait wells, fish boxes, coolers, dive flags and charts.
84001 Overseas Highway
Islamorada, Florida 33036
(305) 664-0091
www.boatrentalsinthekeys.com

A1A Watersports & Boat Rentals
Located behind the Days Inn in Islamorada, they Offer jet-ski, boat, stand-up paddleboards, kayaks, snorkeling gear and fishing pole rentals.
(305) 664-8182
www.keyswatersports.com

JSK Watersports of the Florida Keys
Located in Tavernier, next to the Old Tavernier restaurant, they rent jet-skis for exploring the surrounding waters.
90311 Old Highway
Tavernier, Florida 33070
(305) 998 -9373
www.jskwatersports.com

All In Watersports
Located at Hog Heaven is Islamorada, they offer  a variety of watersports including parasailing, snorkeling,  jet skiing, completely clear kayaks and stand up paddle boards. They also offer full “Day Of Fun” packages on the “Tiki Boat” that include multiple watersports, inflatable water toys and lunch.
85361 Overseas Highway
Islamorada, Florida 33036
(305) 900 – 6498
www.allinwatersports.com

Spray Waterports
They are located on the beach at the newly renovated Postcard Inn (formerly Holiday Isle). Jet ski and boat rentals are offered as well as an award-winning 26 mile guided jet-ski tour.
84001 Overseas Highway
Islamorada, Florida 33036
(305) 664-0075
www.spraywatersportsofthekeys.com

Seamonkeys Watersports
Located at AmaraCay resort in Islamorada, Seamonkeys is a full service dive shop that also offers waterspouts rentals. They have Hobie Cat sail boats, stand-up paddleboards, kayaks, wave -runners and paddleboat rentals.
80001 Overseas Highway
Islamorada, Florida 33036
(305) 664-4555
www.seamonkeydivers.com

Islamorada Watersports
2 locations – one at Whale Harbor marina and the other at Bud & Mary’s marina. IWC rents boats and jet-skis and offers fishing/snorkeling charters as well as eco-tours and sunset cruises.
84001 Overseas Highway
Islamorada, Florida 33036
(305) 664-2463
(305) 432-9788
www.sevensports.com



Marathon

Marathon is located in the middle of the Florida Keys, and the famous Seven-Mile Bridge at it’s western edge is the gateway to the lower keys. There are several outfitters on the island that rent boats. You can explore the waters around the island, local reefs and/or fish the abundant waters under  the Seven-Mile Bridge. 

Crusin’ Tikis Marathon
1021 11th Street – Ocean Next to Lazy Days South Marathon, FL 33050
(855) 539-8454
www.cruisintikismarathon.com

Marathon Boat Rentals
12240 Overseas Hwy, Marathon, FL 33050
(305) 731-0595
www.marathonboatrental.com

All Aboard Boat Rentals
63 Coco Plum Drive Marathon, FL 33050
(305) 849-5567
www.allaboardboatrentals.com
www.allaboardboatrentals.com

Coco’s Boat Rentals
50 Coco Plum Drive Marathon, FL 33050
(305) 432-7021
www.cocosboatrentals.com

Island time Boat Rentals
Between 7 Mile Bridge & Conch Key Marathon, FL 33050
(305) 998-8592..
www.islandtimeboatrental.com

Key West

Most of the resorts in Key West have watersports amenities that include, boat, kayak,  jet-ski and stand-up paddle-board rentals, but Key West is also home to the Tall Ships, Cruisin’ Tiki’s franchises and Ferry to the Dry tortugas and Fort Jefferson. Experience a thrilling sailing adventure on a Schooner, or motor around the island with a group of friends on you own private floating Tiki Bar!

Dry Tortugas National Park and Fort Jefferson Ferry
100 Grinnell Street Key West, FL 33040
(305) 294-7009
www.drytortugas.com

Fun In The Sun Charter Boat Rentals
6000 Peninsular Avenue Key West, FL 33040
(305) 510-3523
www.boatrentalsinkeywest.com

Fury Water Adventures
241 Front Street Key West, FL 33040
(855) 407-2475
www.furycat.com

Goal Tending Services
5130 Overseas Hwy Slip #18 Hurricane Hole Marina Key West, FL 33040
(305) 916-0990
www.goaltendingservices.com

Key West Party Boats
711 Eisenhower Drive Key West, FL 33040
(305)t 916-0990
www.keywestpartyboats.com

Low Tide Charters
Hurricane Hole Marina5130 Overseas Highway, Key West, FL 33040
(305) 600-1301 
www.lowtidecharter.com

Native Sun Private Charters
5950 Peninsular Avenue Key West, FL
(305) 923-9119 
Classic Harbor Line Sailing Ship
Behind Schooner Wharf Bar, 202 Williams St, Key West, FL 33040
(305) 293-7245
www.sail-keywest.com

Cruisin’ Tikis Key West
Mellow Ventures 1605 N. Roosevelt Blvd, OR Hurricane Hole Marina 5130 Overseas Hwy, Key West, FL 33040
(833) 845-4759
www.cruisintikiskeywest.com