Top North America Sailing Trips

Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay, powered...

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as...

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail....

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego...

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat...

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your...

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on...

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way...

Experience Isla Mujeres the Xcaret way on a luxurious catamaran tour across the Caribbean Sea. Start your day snorkeling at the vibrant El Meco reef,...

Experience a breathtaking sunset sail on the Cabo San Lucas Bay aboard a luxury catamaran, complete with delicious appetizers and an international open bar. After...

You'll love visiting the Arch of Cabo San Lucas! - Experience breathtaking views of the stunning sunset where the Sea of Cortez meets the Pacific...

Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a...

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the...

If you are looking for the tropical getaway of your dreams, then get ready to discover Isla Mujeres, the women’s Island. Your day starts with...

Escape to the open waters of Vancouver on a sailing adventure that offers the best of the city’s scenic vistas. This 2.5-3 hour sailing experience...

This is a unique experience because you get to sail a 33' boat with a licensed captain. You can be involved as much or as...

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of...

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area...

Captain Hook’s Cancun tour offers an immersive experience unlike any in the area. More than just a cruise, it’s a dinner-show aboard an authentic 18th...

Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these waters back in 1792. From Seattle’s Shilshole...