Fort Myers Beach Sailing Trips | True North Sailing

Sailing Adventures from Fort Myers Beach, Florida

Sail Fort Myers Beach

Black and white image of a sailboat sailing on open water under clear skies.

Come sail away on a true adventure! True North Sailing Charters offers captained sailing trips that take you on an unforgettable sailing experience in Fort Myers Beach, Florida to experience the Gulf by water on a beautiful sailing catamaran.

This unique experience is perfect for travelers who want to get out and explore one of the most beautiful sailing destinations in the world.

Fort Myers Beach Adventures

3 Hour Sailing Adventure

Fort Myers Beach Sailing Excursion

Set sail on a three-hour adventure from Fort Myers Beach. Begin your journey through lively Matanzas Pass, a hub of bustling boat traffic, people-watching, and playful dolphins riding the current.

Once in open water, hoist the sails and explore the Gulf of Mexico. Depending on the conditions, we’ll sail along Fort Myers Beach or toward the scenic shores of Sanibel Island.

Customize your trip with an optional stop at Bunche Beach Preserve in San Carlos Bay, where you can swim, paddleboard, or explore by Super Dinghy. Or, continue sailing the Gulf, soaking in the beauty of the water and coastline.

This flexible trip offers the perfect mix of relaxation, exploration, and unforgettable memories.

$395
Private trip that includes up to 6 guests

1:00pm Daily

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2 Hours Mangrove Raft Adventure

Adventure Rafting in the Mangroves

Experience an unforgettable adventure rafting trip through the serene mangroves of Fort Myers Beach on an adventure raft! Drift through winding waterways, marvel at the lush surroundings, and spot incredible wildlife like manatees, dolphins, and exotic birds. Perfect for nature lovers and thrill-seekers alike, this guided journey blends relaxation, exploration, and adventure.

$40 per person
$10 child discount

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Sailing Trip Itinerary

Discover the Joy of Sailing in the Fort Myers Beach!

Embark on a captivating sailing trip from Fort Myers Beach, where every moment offers something new to discover. Your adventure begins with a journey through Matanzas Pass, a lively waterway nestled between Estero Island and San Carlos Island. Here, you’ll enjoy excellent people-watching, bustling boat traffic, and perhaps even a visit from playful dolphins riding the current.

Once clear of the channel, the real magic begins. Feel the breeze as we hoist the sails and head into the Gulf of Mexico. Depending on wind and wave conditions, we’ll glide along Fort Myers Beach or make our way toward the scenic shores of Sanibel Island.

From there, it’s your choice! Anchor in the tranquil Bunche Beach Preserve within San Carlos Bay, where you can swim, paddleboard, or explore by super dinghy. Alternatively, continue sailing the Gulf, enjoying scenic views and the serene rhythm of the water.

This flexible and personalized journey is perfect for relaxation, exploration, and making unforgettable memories on the water. Book your adventure today!

Photos

Hands holding seashells over calm blue water.

Straw hat hanging on a sailboat helm, with ocean views in the background

Reviews

Drone view of Echo, a sailing catamaran, gliding on calm blue waters during a scenic Fort Myers Beach sailing tour.

The Boat

Take a look at "Echo", our 35 foot Catamaran featuring a comfortable shaded back salon with steps right down to the water. The first thing you notice when stepping inside Echo is all the natural light that the large windows bring in so even when your inside during your adventure you won't miss a thing. The main salon is the heart of the boat, a gathering place for great conversation.

"Adventure Raft"

The Ultimate Adventure Raft

Our 13’ catamaran-style Adventure Raft is perfect for exploring the narrow mangrove trails that only a small shallow draft boat can navigate. With its stable design, it provides a smooth ride for a small private group or couple. It is perfect for beach landings and accessing secluded spots. Whether it’s a quick hop to a quiet shore or a longer ride to explore coastal mangrove trails, This little boat ensures an unforgettable adventure!

Red 13’ Takacat dinghy floating on calm water, ready for beach access and exploration during a sailing trip.

Silhouette of a person walking along a sandy beach by calm, reflective water

Hands gently holding white sand dollars against a backdrop of soft beach sand.

Hand holding a single seashell with the ocean in the background

Waterfront Views

Dolphin and Wildlife Watching

Shelling and BeachCombing

See Fort Myers Beach like never before on a captained sailing adventure. Glide across the sparkling Gulf waters, taking in stunning coastal views and the vibrant marine life. Relax on deck, feel the sea breeze, or cool off with a swim in the calm waters. This unique perspective of Fort Myers Beach combines relaxation, exploration, and unforgettable memories on the water.

Witness the beauty of dolphins in their natural habitat as they often swim and play alongside the boat. While sightings can’t be guaranteed, these playful creatures are known to frequent the area, creating magical moments for our guests. Enjoy a relaxing sail with the chance to spot one of the Gulf’s most beloved residents!

Discover some of the Gulf Coast’s most pristine beaches, perfect for shelling enthusiasts. Stroll along sandy shores, searching for unique and beautiful shells washed in by the tide. Whether you’re looking for a rare find or simply enjoying the peaceful rhythm of the waves, this activity offers a relaxing connection to nature and a chance to take home a piece of paradise.

Plan to bring your own personal items and clothing. The key to being comfortable is having a layer. Activities can include swimming, being on the deck out in sun and wind, and enjoying an evening sunset in a cool breeze.

Young boy playing in the sand on a secluded beach during a family-friendly sailing adventure.

Doodle dog sitting on the deck of a sailboat, enjoying a calm and sunny day on the water.

We are dog friendly! We are happy to welcome your small to medium well behaved dog on your sailing trip. However please do consider how having your dog along will affect your trip as dogs can react differently to being on a boat. Trip itineraries and sailing times may need to be adjusted depending on their needs. Our sailboat is not a good fit for large dogs, multiple dogs, or high shedding dogs.

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On our Fort Myers Beach sailing trips, you’ll have the incredible opportunity to see dolphins playing in the wake, gentle manatees gliding through the water, and an array of coastal wildlife such as sea turtles, pelicans, and ospreys. The odds of spotting dolphins are exceptionally high, as these waters are home to a thriving population. While manatees are a bit more elusive, sightings are common, especially during warmer months. Every trip offers a chance to connect with the vibrant wildlife of the Gulf!