Top Key West Kayaking Tours

Paddle a kayak through mangrove creeks and shallow water on a Key West kayaking tour that offers an up-close look that this unique coastal environment. This guided tour is the perfect way to spot Florida wildlife in a natural habitat.

Kayaking is a great way to experience the Florida Keys but your views are typically limited to what's above the surface of the water. This small-group tour provides clear kayaks that let you discover the underwater world as well. As you paddle, you just need to look below your feet to spot nurse sharks, turtles, jellyfish and more.

Cool off in Key West on a 6-hour water sports tour that features 12 different water activities for you to try, from snorkeling to windsurfing to Wave Runners. Lunch is included, as is a draft beer on the way back to the marina for those over the age of 21.

Enjoy a day of fun in the sun on the Island T’ing adventure off the coast of Key West. Sail away from the island city of Key West to the beautiful blue waters of the Gulf of Mexico on a large catamaran. Hop in a kayak and enjoy a paddle around a natural stand of mangrove. Look for dolphins, stingrays, sea turtles, manatees and more on this full-day adventure. A full breakfast and buffet lunch, plus beer, wine, soft drinks and homemade sangria are included.

Get access to a remote nature sanctuary, known only to Key West locals, during this island adventure. Choose to paddleboard, kayak, snorkel, or just lounge on the sandbar and take in the natural ambiance. Snack, lunch, and use of snorkel equipment included; wine and beer available after activities.

Get ready for fun in the sun on this half-day sailing, kayaking and snorkeling adventure off the coast of Key West. Choose from a morning or afternoon excursion and set sail. Kayak through a maze of mangrove-canopied canals and streams, home to a tropical array of birds, rays, sharks, sport fish and more. Then jump into the water for a snorkeling session above a coral reef with 600 different species of marine life. Relax, feel the warm sea breeze and enjoy the day. Snacks, beer, wine, sodas and water included.

Watch the sun set and the moon rise off the coast of Key West on this sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 70-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset as the sun glistens and gently settles into the water. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer and soft drinks are included.

Explore the clear, calm waters of Key West at your own pace with a single or double kayak rental. Choose a morning or afternoon session, and after a brief introductory lesson, head out on the water. Glide over seagrass and through mangrove tunnels, keeping your eyes open for fish, birds, sharks, rays, and manatees.

Enjoy an afternoon of swimming and snorkeling on this cruise off the coast of Key West. Spend a relaxing afternoon on a 69-foot catamaran headed to North America's only living coral barrier reef for the adventure of a lifetime. Pass some of Key West’s top attractions on the way, then dive right in to see more than 600 species of colorful fish, coral, and other sea life. This cruise includes professional snorkeling gear and instruction plus beer, wine, and soft drinks.

Explore the only living coral reef in North America during this snorkeling adventure from Key West. Sail aboard a state-of-the-art catamaran as you voyage toward the reef. Receive snorkeling guidance from your knowledgeable crew, making this experience perfect for first-time snorkelers. Use of sanitized snorkel gear and beer, water, and champagne on the morning trip or margaritas on the afternoon trip provided.

Paddle through the mangroves, located at the southwest corner of the island, before reaching the salt ponds on this guided kayaking tour. Learn about the history of Key West and South Florida, as well as the local flora and fauna along the way. You also paddle through the Gulf of Mexico and Cow Key Channel as you head to the mangroves.

Explore the patch reefs, mangrove islands, and waterways of Key West on a 6-hour cruise and snorkeling tour aboard a wooden sailing schooner. Take a hand at the wheel on your way across the Gulf of Mexico, kayak through the mangroves, then snorkel through patch reefs and sponge gardens. This 6-hour tour includes lunch and access to an open bar on the return sail to Key West.

Save time and money in Key West on this all-inclusive, full-day excursion. Enjoy a day of sailing, snorkeling, and kayaking off the coast. Visit the Key West National Wildlife Refuge and explore an underwater world full of colorful fish and coral. Includes a buffet lunch with unlimited beer, wine, and soft drinks.

If Key West isn’t a paradise enough, you can up the ante and spend the perfect day on the water with this half-day, customizable private boat trip. Jump on board and let the captain help you make the experience as memorable as possible. Fishing? Snorkeling? Kayaking and sunbathing? You can do it all with equipment provided by the captain. Float on a pool noodle and sip on soda while you enjoy quality time under the sun.

This trip was uniquely created for a brand new experience in the florida keys. Explore the back country and secluded sandbars like never before done in Key West.

Nature lovers and eco-adventurers will love this low-key tour. Take a pontoon boat to explore mangrove forests, winding waterways, and mangrove-lined tidal creeks. Enjoy kayaking, stand-up paddleboarding, or snorkeling in a diverse marine ecosystem. Snacks and drinks are provided and guests are welcome to bring lunch, which can be savored on a deserted sandbar.

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass.

Explore the Gulf of Mexico from Stock Island and witness an unobstructed view of the sunset on this guided kayaking tour. This tour is designed for all skill levels and includes all of the necessary kayaking gear including lifejackets, lights, and whistles. Plus, score beautiful photos of your experience with an assist from your guide.

It’s important to note why your paddleboard and kayak experience will be unique with Up the Keys Watersports. There are a lot of variables we consider to ensure you get the very most out of your Key West watersport experience. Based on the wind, tide, current and water clarity, your professional tour guide intentionally plans your paddleboard and kayak launch spots the week of your scheduled trip. The safety of our customers and employees is our number one priority and we work hard to make sure that we minimize any risks related to unsafe conditions. With this model, we can also minimize the number of cancellations due to unsafe conditions that might have been present at a pre-designated launch spot. No experience is necessary! The tour will start with a quick overview for anyone that is new to the sport or needs a refresher.

Help beautify the environment while learning about the Florida ecosystem during this Key West waterway cleanup and educational tour. Join the Blue Moon Kayak group in cleaning up Cow Key Channel. As you pick up trash and debris, the guides will teach you about decomposition rates and how these items negatively impact the landscape. You’ll help reduce pollution while enjoying a relaxed kayak excursion.

Smathers Beach full day pass and activities. This is Key West’s best public. Jump on a paddle board, kayak or hobie cat & explore the Key West Atlantic coast. Sail on a Hobie cat in the crystal clear waters. Beach pass includes a choice of a parasailing ride or chair & umbrella. Enjoy a full day with this all inclusive activity package.

Fun in the sun when you make it over to Smathers Beachand have the best day with unlimited use of water activities. Go kayaking, paddle boarding, sailing or just seat in your beach chair and umbrella and enjoy the sun. Make sure to be at the check in for you sunset cruise with live music and open bar no later than 4:15 check in for a 5pm departure. On the 2 hour Sunset cruise you will have an open well bar which includes rum-runners, margaritas, mixed drinks, draft beer, wine, champagne & soft drinks. We will service finger food appetizers like Jamaican jerk chicken sliders on Hawaiian rolls, BBQ meatballs, veggie trays, cheese & cracker trays, Pita & hummus.