Top North America Sailing Trips

A unique two-hour sailing Experience aboard our 35-foot sailboat, Luna. Limited to six people. Watch for playful dolphins, sea lions, and pelicans. Get hands-on or...

Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seabreeze Marina in downtown Charleston. Enjoy stunning waterfront views and local...

To cross the calm waters of the Caribbean, there is no better means of transportation than a catamaran. These specialized sailboats have multiple hulls so...

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of...

Celebrate Mexican culture like never before at Xoximilco by Xcaret—a one-of-a-kind floating fiesta through the canals of Cancun! Step aboard a colorful trajinera (traditional gondola-style...

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa,...

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers...

Join one of the most wonderful wildlife experiences in Cancun during the whale shark season! Explore the Caribbean Sea aboard a small-group boat for a...

Experience an unforgettable encounter with the world's largest fish in the crystal-clear waters of the Mexican Caribbean! Enjoy a small-group experience with a maximum of...

Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural beauty, the tranquility of the sunrise and respect for...

Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in...

From Sailboatcancun we offer sailing courses aboard a 75 feet sailboat with an experience of more than 25 thousand miles sailed by different oceans. The...

Set sail on a 3-hour journey through the stunning St. Margarets Bay, blending sailing excitement with the beauty of Nova Scotia’s coastline. Departing from Shining...

Step aboard a boat and experience whale watching like never before. On this special cruise, see humpback whales in their natural habitat and hear them...

Ideal for cruisers with at least 8 hours in Costa Maya. Chacchoben + Bacalar: Sailing or The Rapids Your adventure begins at Costa Maya Cruise...

This Key West experience lets you enjoy all that the island has to offer. Sail on a sleek catamaran along the smooth waters of the...

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted...

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and...

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and...

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the...