Top North America Sailing Trips

The Hidden Gem Tour! Explore Bacalar’s secret lagoons and the historic Pirate Route, float gently in peaceful currents, spot wildlife, and enjoy fresh snacks and...

Discover with us the breathtaking lagoon of the seven colors. We tell you the true stories of the Pirates of the Caribbean. Learn more about...

As a team we try to create journeys that are worth investing your time and confidence. We try to do our best to get out...

This tour combines three of the bay’s most iconic locations in one all-inclusive adventure. Travelers love the balance of snorkeling, beach time, and jungle exploration—plus...

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon....

Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This romantic sunset cruise on Cabo San Lucas Bay...

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that...

This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is best to go see our San...

This private morning sail is a great way to start the day. Mornings are best to go see San Diego's wildlife because there is little...

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cruise along the stunning Waikiki coastline aboard the either...

Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the water, and offers a great introduction to sailing. Guests are encouraged...

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under...

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran...

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both...

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention...

This interactive experience is perfect for families, kids, and anyone who loves the thrill of the hunt—whether you’re spotting shark teeth, collecting shells, or simply...

• Enjoy the turquoise waters of Cozumel aboard one of our luxury sailing catamarans. • Snorkel and marvel at the wide array of tropical fish...

Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau sailboats, taking in breathtaking views of Puerto Vallarta’s coastline and the majestic Sierra...

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty...

Start your day with a hotel pickup or directly at the marina, then head out to open sea through the spectacular mangrove channels. The bar...