Sailing Adventures from Key Largo, Florida

Sail Key Largo

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 Key Largo, Florida to experience The Florida Keys 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.

Key Largo Sailing Adventures

3 Hour Afternoon Sailing Trip

Key Largo Sailing Excursion

Set sail on a breathtaking 3-hour sailing adventure in Key Largo with True North Sailing Charters. Glide across the turquoise waters of the Florida Keys, where gentle sea breezes and stunning coastal views create the perfect escape. Whether you’re looking to relax, spot wildlife, or take the helm under expert guidance, this private charter offers an unforgettable experience.

Ideal for couples, families, or small groups, our intimate sailing trip is the perfect way to soak in the beauty of the Keys. No sailing experience needed—just bring your sense of adventure!

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

$79 per person
Public trip with up to six guests
or
$395 private boat
Private trip that includes up to 6 guests

1:00pm Daily

Book Now

FMB Sailing Sunset-min_edited_edited.jpg

2.5 Hour Private Sunset Sail

Key Largo Private Sunset Sail

Experience the magic of a Florida Keys sunset aboard True North Sailing Charters. This 2.5-hour private sailing adventure offers front-row seats to nature’s most stunning display as the sun dips below the horizon, painting the sky in brilliant hues of orange, pink, and gold.

Feel the gentle breeze, sip your favorite drink, and watch for dolphins and seabirds as you sail through the calm waters of Key Largo. Perfect for couples, families, and small groups looking to unwind and soak in the beauty of the evening sky. Relax, reconnect, and let the ocean set the perfect scene.

$79 per person
Public trip with up to six guests
or
$395 private boat
Private trip that includes up to 6 guests

1:00pm Daily

Book Now

Overnight Sailing Adventure 2-5 Nights

Florida Keys Sailing AdVenture

Set sail on an unforgettable adventure with True North Sailing Charters as we explore the breathtaking islands and coastline of Southwest Florida! Departing from Fort Myers Beach aboard our catamaran “Echo,” this customizable journey offers 2- to 5-day sailing trips tailored to your perfect getaway. Discover turquoise waters, pristine beaches, and hidden gems along the Gulf Coast, with opportunities to snorkel, relax on secluded islands, and soak in stunning sunsets. If you are seeking an escape from the cold this multi-day sailing adventure, promises relaxation, exploration, and lasting memories. Contact us today with your dates to plan your ideal trip!

$1,500 per day
Includes up to six guests

Key Largo Sunset Sail

Private Sunset Sail Aboard the Catamaran Echo

Key Largo, Florida

Step aboard the luxurious Catamaran Echo for an unforgettable sunset sail along the scenic coastline of Key Largo, Florida. This exclusive 2.5 hour experience offers a front-row seat to nature’s most breathtaking show as the sun sets over the shimmering waters of the Florida Keys.

Relax on the spacious deck of our sleek and stable catamaran, designed for comfort and panoramic views. As the warm gulf breeze gently surrounds you, sip on a refreshing drink and soak in the tranquil atmosphere. Look out for playful dolphins, gliding seabirds, and other marine life that often accompany our journey, adding an extra touch of magic to your evening.

Perfect for couples, families, or small groups, our sunset sail is the ideal way to celebrate a special occasion or simply unwind while experiencing the natural beauty of Florida’s coast. With our friendly and knowledgeable crew at the helm, your evening promises to be as relaxing as it is memorable.

Highlights:

• 2.5 sunset sail aboard the luxurious Catamaran Echo

• Stunning views of Key Largo and the Florida Keys

• Opportunities to spot dolphins and other marine life

• Intimate and relaxing experience with your private group

Whether you’re visiting Key Largo or a local seeking a unique evening escape, let the Catamaran Echo make your sunset sail a memory you’ll treasure forever.

Book your sunset adventure today!

Catamaran Sailing into the Sunset at Fort Myers Beach, Florida

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Afternoon Sailing Trip Itinerary

Discover the Joy of Sailing in Key Largo!

Embark on a captivating sailing trip from Key Largo, Florida, where every moment brings a new adventure. Your journey begins as we navigate the sparkling waters of Blackwater Sound and through the scenic mangrove-lined channels of the Florida Keys. Keep an eye out for playful dolphins, graceful manatees, and a variety of seabirds soaring above.

Once we reach the open water, the true magic begins. Feel the ocean breeze as we hoist the sails and glide into the turquoise expanse of Florida Bay or beyond to the Atlantic Ocean, depending on wind and weather conditions. Enjoy breathtaking views of the unspoiled coastline, nearby coral reefs, and endless horizons.

From there, it’s your choice! We can drop anchor in a secluded cove, where you can swim, snorkel, or relax on deck with a drink in hand. Or, continue sailing along the picturesque coastline, soaking in the serenity of the sea.

This flexible and personalized sailing experience is perfect for relaxation, adventure, and making unforgettable memories on the water. Book your Key Largo sailing adventure today!

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 the Florida Keys 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 Key Largo 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.

CLICK TO BOOK NOW!

On our Key Largo 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 Keys!