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Sailing Trips

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2 Hour Day Sail to the Statue of Liberty

2 Hour Day Sail to the Statue of Liberty

Offering a premium sailing experience, the Schooner America 2.0 is the newest, largest, most elegant ship designed for our fleet. Added to…



2-Hour Monterey Bay Family Sailing Cruise

2-Hour Monterey Bay Family Sailing Cruise

This cruise departs at 11 A.M and returns to port by 1 P.M! Enjoy a 2-hour captained sailing excursion…



3 Hour Private Sail For Up To 6 People

3 Hour Private Sail For Up To 6 People

Feel the wind in your hair as you sail through the bay as you sip on wine or champagne! With…



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…



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 Afternoon Sail

America's Cup Afternoon Sail

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars…



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…



Big Island Hilton Waikoloa Sunset Sail

Big Island Hilton Waikoloa Sunset Sail

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



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 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…



City Lights and Boston Skyline Harbor Sail

City Lights and Boston Skyline Harbor Sail

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



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…



Cruise Boston Harbor on our 67 Foot Tall Ship Schooner

Cruise Boston Harbor on our 67 Foot Tall Ship Schooner

Come aboard the "little sister" of our tall ship fleet, the 67-foot  Liberty Star and take a trip back in time…



Day Sail to Statue of Liberty on Adirondack

Day Sail to Statue of Liberty on Adirondack

Offered April through early November: Experience New York like you never have before on this two-hour sail aboard the Adirondack, an…



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…



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