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Sailing Trips

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2-Hour Harbor Sail in San Diego with Maritime Museum Ticket

2-Hour Harbor Sail in San Diego with Maritime Museum Ticket

Welcome aboard the queen of the fleet in San Diego, the luxury yacht America, for the premium harbor cruise in…



2-Hour Monterey Bay Family Sailing Cruise

2-Hour Monterey Bay Family Sailing Cruise

Choose from two departure times when you book. Enjoy a 2-hour captained sailing excursion with your family and friends on…



3 Hour San Diego Sunset Sail

3 Hour San Diego Sunset Sail

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that…



3-Hr Private Endless Summer Special

3-Hr Private Endless Summer Special

This is a 3-Hour Private Sailing Charter that can accommodate up to SIX passengers.  A Licensed Captain will navigate your…



90 Min Key West Harbor Sail

90 Min 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…



Adirondack III City Lights Sail

Adirondack III City Lights Sail

Enjoy a 1.5-hour sail around Boston Harbor, see the city and iconic buildings light up the night, enjoy the glittering…



Adirondack III Day Sail

Adirondack III Day Sail

Enjoy a 2-hour sail aboard Adirondack III- inspired by the pilot schooners of the 1890s.  Sail past the seaport district,…



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…



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…



Bugeye Backcountry Schooner Eco Tour

Bugeye Backcountry Schooner Eco Tour

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



Catamaran Sailing and Snorkel Adventure on Kaneohe Bay

Catamaran Sailing and Snorkel Adventure on Kaneohe 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 Fireworks Sail

Chicago Fireworks Sail

A Special Event Sail! Relax and enjoy Navy Pier’s spectacular fireworks display from the best seat in town. Then, get…



Chicago Lakeside Architecture Tour

Chicago Lakeside Architecture Tour

Leave the hustle and bustle behind, and enjoy a leisurely Skyline Sail aboard Chicago’s Official Tall Ship. Our crew today…



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 Harbor Morning Cruise

Classic Sailboat Harbor Morning Cruise

Experience the bustling activity of the bay, wildlife, and a stunning view of the city skyline on a San Diego…



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…



Hawaii Pirate Ship Adventures

Hawaii Pirate Ship Adventures

Enjoy fun for the whole family during our live pirate show aboard the Treasure Seeker!  Join our pirates in their…



History of Chesapeake Bay Sailing Tour

History of Chesapeake Bay Sailing Tour

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



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