TOP 30 Florida kayaking adventures in Islamorada, Florida

Paddle the Florida Keys is a top-rated institution located in Tavernier, Florida, offering kayak and paddleboard rentals, eco-tours, sales, and deliveries. Whether you're a beginner or experienced paddler, our professional guides will lead you on an unforgettable journey through the beautiful mangrove tunnels and seagrass meadows of the Florida Keys. With flat rates and the option to rent for 24 hours or longer, you can paddle at your own pace and explore at your leisure. Owner Deven Carrier, a lifelong Keys local and competitive paddle board racer, is passionate about the sport and has helped grow the local paddlesport community for over a decade. Our retail store offers a wide selection of paddle boards, skateboards, gear, and accessories, ensuring you have everything you need for a day on the water or onshore.

The Islands of Islamorada is a charming lodging institution located at 82779 Old Highway in Islamorada, Florida, United States. Nestled in the heart of the Florida Keys, this picturesque resort offers guests a serene and relaxing retreat surrounded by the beauty of the islands. With comfortable accommodations, stunning ocean views, and easy access to a variety of outdoor activities such as fishing, snorkeling, and kayaking, The Islands of Islamorada is the perfect destination for a peaceful getaway. Whether you're seeking a romantic escape or a family vacation, this institution provides a tranquil and unforgettable experience for all who visit.

I Can See CLEAR Kayaking is a unique travel agency located at 96 Madeira Road in Islamorada, Florida, United States. Specializing in clear kayaking adventures, they offer a one-of-a-kind experience where guests can explore the crystal-clear waters of the Florida Keys while paddling through mangrove forests and coral reefs. With knowledgeable guides and top-of-the-line equipment, I Can See CLEAR Kayaking provides a safe and unforgettable journey for nature lovers and adventure seekers alike. Join them for a truly immersive and mesmerizing kayaking experience unlike any other.

Pines and Palms Adventures is a travel agency located at 80401 Old Highway in Islamorada, Florida, United States. This family-owned resort offers boutique-style accommodations with oceanfront cottages and suites, creating a peaceful tropical village for an authentic Florida Keys experience. Guests can enjoy daily natural spectacles, fiery sunrises, and a laid-back lifestyle while staying at this resort. The oceanfront climate-controlled pool allows for a relaxing break in the day, with views of the Atlantic Ocean. Seasonal yoga classes are also available for guests to rejuvenate their body and soul in paradise. Pines and Palms Resort prides itself on personalized service that makes guests feel like family, leading to many returning visitors who appreciate the charm and hospitality offered here.

Florida Keys Boat Charters is a premier travel agency located in Islamorada, Florida. Our expert team specializes in providing top-quality boat charters for exploring the beautiful waters of the Florida Keys. Whether you're looking for a relaxing day on the water or an exciting fishing adventure, we have the perfect charter for you. With our convenient location on Overseas Highway, we make it easy for you to start your unforgettable journey through the stunning Florida Keys. Book your charter with Florida Keys Boat Charters today and experience the ultimate in luxury and adventure on the water.

Otherside Boardsports is a premier store located in Islamorada, Florida, specializing in all things boardsports. Whether you're into surfing, paddleboarding, or kiteboarding, this store has everything you need to hit the waves in style. From top-of-the-line equipment to stylish apparel and accessories, Otherside Boardsports is your one-stop shop for all your boardsport needs. Visit us at 82758 Overseas Highway and gear up for your next adventure on the water.

Sea Monkeys Water Sports is a premier destination for all your water adventure needs in Islamorada, Florida. Located at 80460 Overseas Highway, our store and travel agency offers a wide range of activities including Scuba Diving Trips, Night Diving Trips, Snorkel Trips, Sandbar Trips, Eco-Tours, and Sunset Cruises. Experience the thrill of diving in the Florida Keys with our Six Pack Diving trips, suitable for all experience levels. Our boat can quickly take you to dozens of dive and snorkel sites, with all dives including tank, weights, and wet suit. For a more intimate experience, our Night Diving trips are limited to 4 guests per boat and include the necessary equipment for a unique underwater adventure.

Located in the heart of Islamorada, Florida, Backcountry Cowboy Outfitters is your one-stop shop for all your outdoor adventure needs. Whether you're looking to rent a bicycle, kayak, or paddleboard for a day of exploration, or in need of high-quality outdoor clothing and gear, we have you covered. Since our opening in September 2004, we have been dedicated to providing top-notch customer service and expert advice to help you make the most of your outdoor experiences. Our knowledgeable staff can help you choose the perfect equipment for your individual or family adventures, whether you're looking for a relaxing sunset paddle or an exhilarating day trip.

Located at 81801 Overseas Highway in Islamorada, Florida, Cheeca Lodge & Spa offers a luxurious retreat surrounded by turquoise waters, towering palms, and calm breezes. This oceanfront resort invites guests to experience barefoot luxury and embrace the laid-back lifestyle of the Florida Keys. With a range of thrilling activities, luxurious accommodations, exceptional dining options, and unparalleled relaxation, Cheeca Lodge & Spa promises an unforgettable getaway. Whether you're looking to celebrate love with a picturesque oceanfront wedding or host a productive corporate retreat, Cheeca Lodge & Spa offers the perfect venue. With over 15,000 square feet of meeting space, impeccable service from event planners, and a stunning backdrop of the Atlantic ocean, this resort is ideal for weddings, sales meetings, conferences, and more.

Island Bay Resort is a tropical oasis located at 92530 Overseas Highway in Tavernier, Florida, United States. Our beachfront location on the Florida Bay offers stunning sunsets and a relaxing atmosphere surrounded by palm trees and flowering plants. Whether you're looking to unwind and escape everyday stress or seeking adventure in the Florida Keys, our resort has something for everyone. Centrally located between Key Largo and Islamorada, just two hours from Key West or the Miami/Ft. Lauderdale area, Island Bay Resort is the perfect destination for your next vacation. Enjoy our tiki huts, hammocks, swimming, snorkeling, boating, and sunbathing on our private beach.

Located at 80401 Old Highway in Islamorada, Florida, the Pines and Palms Resort is a charming lodging institution that offers boutique-style accommodations right on the Atlantic Ocean. The resort is designed as a peaceful tropical village, with oceanfront cottages and suites for an authentic Florida Keys experience. Guests can enjoy daily natural spectacles, fiery sunrises, and a laid-back lifestyle that embodies the essence of Keys life. The resort boasts an oceanfront climate-controlled pool for relaxation, as well as seasonal yoga classes for rejuvenation. With personalized service and genuine hospitality, guests are welcomed as family at Pines and Palms Resort. Visitors can take advantage of complimentary kayaks, paddle boards, and bike rentals, as well as sunset sails and private fishing charters for added adventure.

Blackwater Fishing Charters is a family-run business located in Islamorada, Florida, offering the best inshore fishing experience in the Florida Keys. Captain Eric Scoble, a fifth-generation Conch and expert backcountry fishing guide, leads the charters with over 25 years of personal experience. With a focus on light tackle fishing and using live bait, Captain Eric ensures a memorable and successful fishing trip for all guests. Whether you choose to explore the calm waters of Florida Bay or venture into the Gulf of Mexico, Blackwater Charters guarantees a day filled with action and beautiful sights. From catching Yellowtail Snapper to Tarpon and Redfish, the possibilities are endless with Captain Eric at the helm. The Gulf Wreck trip and Spanish Mackerel trip are also popular options for those seeking a variety of fish species. With Captain Eric's extensive knowledge of the local waters and dedication to providing a top-notch fishing experience, Blackwater Fishing Charters is the ultimate destination for anglers of all levels. Book your trip today and create lasting memories on the waters of Islamorada!

Barefeet Vacation Rentals is a real estate and travel agency located at 103400 Overseas Highway in Key Largo, Florida. Specializing in Key Largo and Islamorada vacation rentals, Barefeet Rentals offers a variety of private homes and condos to fit any budget, some even featuring docks for boaters. Whether you're a boater, fisherman, scuba diver, sun worshiper, or snowbird, Barefeet Rentals has something for everyone in the fabulous Florida Keys. From snorkeling coral reefs to deep-sea fishing excursions, there are endless activities to enjoy in this tropical paradise. Explore the Everglades National Park on an airboat tour or kayak through the Florida Keys for a unique eco-adventure.

Blackbeard Private Charters is a premier travel agency located at 85920 Overseas Highway in Islamorada, Florida. Specializing in private custom boat charters, Blackbeard Charters offers a unique opportunity to experience the Florida Keys like a local. Whether you're looking to relax at the Islamorada Sandbar or explore the vibrant reefs in the upper Keys, our experienced team is dedicated to providing you with the trip of a lifetime. Swim among tropical fish, soak up the sun, and create unforgettable memories with Blackbeard Private Charters.