Otherside Boardsports

THE STORIED FLORIDA KEYS SET THE STAGE FOR SOME OF THE BEST PADDLING IN THE WORLD. TRANQUIL BLUE & GREEN SEAS STRETCH AS FAR AS THE EYE CAN SEE INTO BOTH THE FLORIDA BAY AND THE ATLANTIC OCEAN. CLEAR, CALM, SHALLOW WATERS HOST AN INCREDIBLY RICH ECO SYSTEM ABOVE AND BELOW THE SURFACE AND WE CAN'T WAIT TO SHARE YOUR PADDLEBOARDING OR KAYAKING ADVENTURE WITH YOU! LET US GUIDE YOU TO THE VERY BEST SECRET SPOTS, OR CHOOSE TO RENT OUR TOP NOTCH EQUIPMENT AND EXPLORE ON YOUR OWN. oTHErside also offers advanced excursions for experienced paddlers that include two of our offshore state parks (Indian Key State Historic Site, Lignumvitae Key Botanical State Park) as well as paddle/snorkel trips to Alligator Reef Lighthouse, Cheeca Rocks or Caloosa Gardens. Paddleboard yoga classes are available upon request with our certified yoga instructors.

Islamorada Watersports Company @ Bud N' Mary's Marina

For over 15 years, the Islamorada Watersports Company has been serving locals and visitors to the Florida Keys with all kinds of fun out on the water. We specialize in making your vacation experience unforgettable, easy and fun! Call or email us now to begin to plan your trip! Our main activities include Boat Rentals, Waverunner Rentals and the popular "Jet Ski Tour". We have paddleboards and kayaks available for rent too. We operate in Islamorada from Whale Harbor Marina and Bud N Mary's Marina on the north and south end of Upper Matecumbe Key. We can deliver and are happy to ride along to help show you the beautiful area we call home.

Bump and Jump Boat Rental

Sundance Watersports

Experience Classic Keys Activities SNORKELING, PARASAILING, SUNSET CRUISES, SNUBA™, AND PRIVATE CHARTERS Sundance Watersports offers on-the-water excitement for all ages to make for a thrilling and unforgettable vacation. Cindy and George Shattuck opened the doors of Sundance Watersports in 1994 right here in the Florida Keys, and ever since, they’ve been around providing family fun and the best watersports experiences you can get in the Keys. They’re quite proud to have set up shop in Robbie’s on Islamorada, a funky marina that was voted the #1 place in the Keys that every tourist should visit.

Islamorada Watersports Company @ Whale Harbor Marina

For over 20 years, the Islamorada Watersports Company has been serving locals and visitors to the Florida Keys with all kinds of fun out on the water. We specialize in making your vacation experience unforgettable, easy and fun! Call or email us now to begin to plan your trip! Our main activities include Boat Rentals, Waverunner Rentals and the popular "Jet Ski Tour". We operate in Islamorada from Whale Harbor Marina on the north end of Upper Matecumbe Key. We can deliver and are happy to ride along to help show you the beautiful area we call home.

Sand Hopper Adventures

Contagious Offshore Fishing Charter

Welcome aboard! Let Captain Brian Cone help you enjoy a great day fishing! Whether you are an experienced saltwater angler or a total novice, your day on the Contagious will be one you won't ever forget! Because of the spectacular fishing off the shores of Islamorada, this charming fishing community has long had the title, “Sportfishing Capital of the World.” The charter frequently begins at the edge of the reef, catching live bait! You'll enjoy seeing how this is done! There's an art to it and there is no better teacher than Captain Brian! In the winter months, you may be lucky enough to catch a sailfish close to shore. In the summer months, dolphin are the prize and there is no one better at finding the big ones than Captain Brian. Snapper, groupers, kingfish, and tuna are other favorites. Time: We leave the dock at 7:30 am, but we can be a little flexible - it's your trip!

Cruisin' Tikis Islamorada

Enjoy a truly unique cruise along the beautiful waterways of Islamorada. …Tiki Style!

Aquablue Adventures Sandbar Charter & Boat Tours - Islamorada

Aqua Blue Adventures provides an array of full service watersports adventures that can only be had in Islamorada. Whether it’s paddle boarding, snorkeling or a boat charter that includes a combo of all our services, we can do it all. Contact us today, we are located at the Docks of Island Grill or visit our web site to schedule your adventures.

Aquaholic Adventures

Aquaholic Adventures services Key Largo and Islamorada. We specialize in our premium eco tours Day or Night. We have the best mangrove tunnel tours in all of the Florida Keys! Sign up for premium guided mangrove tunnel day or night tours. We have several launch sites throughout the keys, however one of our most popular is Post Card Inn at mile marker 84. You can also head out on your own and leave from the beach and head to the famous sandbar at mile marker 84 Holiday Isle/Postcard Inn. Don’t forget to ask about the Dolphin Paddle in Key Largo. Free delivery to any location though, just ask we know all the best places for the given wind conditions. We aren’t limited to one spot! We can also come to you! Free Delivery to your doorstep!