Top North America Sailing Trips

This experience combines three things you rarely get in one outing: a small-group boat tour, yoga on a Casco Bay island, and a celebratory drink...

Would you like to give your partner the best birthday or anniversary gift during the holidays? Join us in this great adventure that takes you...

Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht into the sunny waters of Okanagan Lake. We...

Within the activities of this tour, it will be bird watching, sailing in an ecological way without motor. We will swim in the places with...

While visiting Puerto Vallarta is a must to take the Pirate Sailboat tour. Enjoying magnificent views of Banderas Bay, take unforgettable photos of this amazing...

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...

Sail along the coast, enjoying the refreshing breeze in this exclusive sailing experience. Marvel at the beauty that makes Los Cabos a unique destination and...

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning...

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 • World Famous Captain Cook Monument at Kealakekua Bay • Red...

Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leaving from Keauhou Bay Pier. Set sail along...

You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see...

Let's go Sailing!  Experience Miami's Biscayne Bay aboard one of Cool Shore Excursions Beneteau stylish vessels in the company of experienced, but mostly fun, well...

You will discover an underwater world. Admire the colorful variety of fish and the different forms that the coral reef has. El Cielo reef is...

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...

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...

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...

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

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...