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Sailing Trips

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90-Minute Key West Harbor Sail

90-Minute Key West Harbor Sail

This 90 minute sailing trip in Key West is the best way to experience the water with friends and/or family…



All Inclusive Water Adventure Excursion in Key West

All Inclusive Water Adventure Excursion in Key West

This full day excursion from Key West includes all the fun things to do in the ocean - kayaking, snorkeling…



America's Cup Sailing Adventure on San Francisco Bay: Day Sail

America's Cup Sailing Adventure on San Francisco Bay: Day Sail

Welcome aboard for a thrilling 2.5 hour sailing adventure aboard USA 76, an International America’s Cup Class racing yacht that…



America's Cup Sailing Adventure on San Francisco Bay: Express Sail

America's Cup Sailing Adventure on San Francisco Bay: Express Sail

Welcome aboard for a family friendly 2 hour San Francisco Bay sailing tour aboard USA 76, an International America’s Cup…



America's Cup Sailing Adventure on San Francisco Bay: Sunset Sail

America's Cup Sailing Adventure on San Francisco Bay: Sunset Sail

Welcome aboard for a thrilling 2.5 hour sailing adventure culminating with sunset over San Francisco Bay. We will sail aboard…



Baltimore Inner Harbor Sailing Experience

Baltimore Inner Harbor Sailing Experience

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the…



Catamaran Sailing and Snorkel Adventure on Kane'ohe Bay

Catamaran Sailing and Snorkel Adventure on Kane'ohe Bay

Sail and snorkel in Oahu's Kaneohe Bay during a 3-hour cruise aboard a small catamaran. Set sail from He’eia State…



Chicago Skyline Sightseeing Cruise

Chicago Skyline Sightseeing Cruise

Leave the hustle and bustle behind! Explore Chicago's shores with a leisurely trip around Lake Michigan. Take in the world-famous…



Classic Sailboat Afternoon Harbor Tour

Classic Sailboat Afternoon Harbor Tour

Family-owned business offering small group sailing tours on San Diego Bay on a unique 1914 replica Friendship Sloop. All boat tours circle…



Classic Sailboat Sunset Sail

Classic Sailboat Sunset Sail

This unforgettable 2.5 hour tour will circle you around the San Diego harbor during the most dramatic part of a…



Craft Beer Sailing Cruise in New York City

Craft Beer Sailing Cruise in New York City

Step aboard one of the largest sailing ships in the US and cruise along New York Harbor while tasting some…



Half-Day Cruise with Kayaking and Snorkeling

Half-Day Cruise with Kayaking and Snorkeling

Don't miss one of the top things to do in Key West—a half-day sailing tour where you can explore the…



History of Chesapeake Bay Sailing Tour

History of Chesapeake Bay Sailing Tour

Learn about the maritime history of Baltimore and the Chesapeake Bay on this 1.5-hour sailing tour. Enjoy being on the…



Java Cat Sail, Kayak and Snorkel Charter

Java Cat Sail, Kayak and Snorkel Charter

Dolphins, sea turtles or "flyin" rays may cross your path as you enter "The Lake", jewel of the Key West…



Key West Backcountry Schooner Eco-Tour

Key West Backcountry Schooner Eco-Tour

Set sail aboard our classically-styled schooner as she departs Key West's Historic Seaport for a full day of sailing and…



Key West Sunset Snorkel Sail

Key West Sunset Snorkel Sail

3 Hour Sunset Snorkel SailSee the Living Coral Reefwatch the World Famous Key West SunsetHave a cool beverage.…



Kona-Kohala Coast Sunset Sail by Catamaran

Kona-Kohala Coast Sunset Sail by Catamaran

Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamaran. Catch the moment the sun…



Lahaina Champagne and Sunset Sail

Lahaina Champagne and Sunset Sail

A perfect Maui experience is not complete without witnessing the beauty of a sunset out on the ocean. Join us…



Lana'i Snorkel and Performance Sail

Lana'i Snorkel and Performance Sail

Sail Maui is proud to offer a destination snorkel sail to the exclusive island of Lana’i. Join us on Paragon…



Molokini Snorkel and Performance Sail

Molokini Snorkel and Performance Sail

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater…



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