Sailing Trips in USA
Top 10 Best USA Sailing Trips
Found 415 Sailing Trips activities in USA. Sort by Popularity. - Page 14Waikiki Friday Night Fireworks Boat Cruise on O'ahu
Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring your favorite beverages and join us for Waikiki's weekly fireworks displ... More

Waikiki Friday Night Fireworks Boat Cruise on O'ahu
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USA
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Exellent27 reviews4.5
Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....
Key West Historic Schooner When And If Sunset Cruise
Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner When And If, commissioned by General George Patton in the late 1930s, and sail into a breathtaking Key West sunset. Raise a champ... More

Key West Historic Schooner When And If Sunset Cruise
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USA
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Superb99 reviews4.8
Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner....
2-Hour Sunset Sail from San Diego
Leave your worries behind as you cruise the San Diego Bay and marvel at the cityscape. The vibrant waterfront offers expansive views of Downtown, Point Loma, and Coronado Island. Experience the setting sun cast its brilliant color... More

2-Hour Sunset Sail from San Diego
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USA
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Superb72 reviews4.8
Leave your worries behind as you cruise the San Diego Bay and marvel at the cityscape. The vibrant w....
Friday Night Catamaran Fireworks Sail with Open Bar
Who doesn't love fireworks, especially with all inclusive drinks? The famous weekly Hilton Hawaiian Village fireworks display seen from the water feels like you’re right under the action! There's no better way to kick off the we... More

Friday Night Catamaran Fireworks Sail with Open Bar
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USA
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Superb55 reviews4.8
Who doesn't love fireworks, especially with all inclusive drinks? The famous weekly Hilton Hawaiian ....
Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate
Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht regattas. Fate is not only the most demanded but also the largest and nicest sailing yacht available for Charter in Charleston, kn... More
Private Tour

Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate
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USA
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Superb39 reviews5
Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht ....
Private Tour
Fun Boat Rental with Captain in Miami Beach - up to 6 people
Upon agreeing to embark on this adventure with us, you'll formalize the arrangement through a straightforward bareboat charter. Now, let's talk logistics. The captain's compensation is a separate matter, settled directly at the ... More
Private Tour

Fun Boat Rental with Captain in Miami Beach - up to 6 people
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USA
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Superb49 reviews4.9
Upon agreeing to embark on this adventure with us, you'll formalize the arrangement through a straig....
Private Tour
Private Sailing on the Miami Bay - Biscayne Bay
Let's go Sailing! Experience Miami's Biscayne Bay aboard one of Destino Charters Beneteau stylish vessels in the company of experienced, but mostly fun, well traveled, passionate captains. A Private Sailing tour aboard Destino ... More
Private Tour

Private Sailing on the Miami Bay - Biscayne Bay
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USA
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Superb74 reviews4.9
Let's go Sailing! Experience Miami's Biscayne Bay aboard one of Destino Charters Beneteau stylish....
Private Tour
Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay
We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We have made a commitment to sustainability and having a minimal impact on the environment ! It is a wholesome adventure that will le... More
Private Tour

Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay
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USA
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Superb12 reviews4.9
We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We ....
Private Tour
Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering
Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also the largest and nicest sailing yacht available for Charter in Charleston, kn... More
Private Tour

Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering
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USA
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Superb40 reviews5
Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht ....
Private Tour
Private Sailboat Charter on San Francisco Bay
Sunny winter days can be the Best on San Francisco Bay! No Fog, gentle breeze and sunshine! 3 hour PRIVATE Charter with a unique experience aboard Carmelita, our beautiful and pristine Catalina 42 sailboat. We provide our clients ... More
Private Tour

Private Sailboat Charter on San Francisco Bay
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USA
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Superb8 reviews5
Sunny winter days can be the Best on San Francisco Bay! No Fog, gentle breeze and sunshine! 3 hour P....
Private Tour
New York City Live Jazz Sail
Step aboard 105-foot Schooner America 2.0, a modern tribute to the first boat that won the America's Cup in 1851, for a 2-hour sail around New York Harbor. Sit back and relax while enjoying live Jazz music played throughout this s... More
Private Tour

New York City Live Jazz Sail
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USA
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Superb13 reviews4.8
Step aboard 105-foot Schooner America 2.0, a modern tribute to the first boat that won the America's....
Private Tour
Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor since 2012, our sailing yachts are the highest quality and operated ... More
Private Tour

Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique
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USA
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Superb31 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour
New York City Skyline Lights Sail
Experience New York City from the water on classic Schooner Adirondack. Gaze at the city lights from the water and enjoy a peaceful setting as you escape the city and take to a quiet harbor at night. Key points about this activ... More
Private Tour

New York City Skyline Lights Sail
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USA
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Superb13 reviews4.7
Experience New York City from the water on classic Schooner Adirondack. Gaze at the city lights fro....
Private Tour
Captain Steve's Sailing Experience on Long Island
Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best enjoyed from the water. With Captain Steve's Sailing Experience, you can experience the beauty of the area from a unique perspecti... More
Private Tour

Captain Steve's Sailing Experience on Long Island
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USA
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Superb10 reviews5
Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best ....
Private Tour

Private 2-Hour Day Sailing Experience
As the first and only sailing tour in Central Florida, Sailing Orlando is committed to sharing the joy of sailing with our community and its visitors. From day sailing to sunset cruises or learning the ropes, our private tours off... More
Free Cancellation
Private Tour
(Saving 20% )

Private 2-Hour Day Sailing Experience
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USA
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Superb45 reviews5
As the first and only sailing tour in Central Florida, Sailing Orlando is committed to sharing the j....
Free Cancellation
Private Tour
(Saving 20% )
Guided Seattle Sailing Adventure from Bainbridge Island
Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning waterfront homes, and maybe even spot whales. Or we could see a nuclear submarine, inbound container ships, or century-old schooners... More
Private Tour

Guided Seattle Sailing Adventure from Bainbridge Island
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USA
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Superb82 reviews5
Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning wa....
Private Tour
2-Hour Private Hilton Head Afternoon Dolphin Watching Sail
This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the North side of the island. During the day, this is generally filled with exciting winds for gre... More
Private Tour

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail
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USA
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Superb121 reviews5
This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind....
Private Tour
Awesome San Francisco Bay Private Sailing Adventure via Sausalito
Sail under the spectacular Golden Gate Bridge, and view the Marin Headlands, Alcatraz and the SF skyline. This is a Private Trip on a sailing yacht! Get a taste for what an experience living, working and voyaging on a sailboat c... More
Private Tour

Awesome San Francisco Bay Private Sailing Adventure via Sausalito
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USA
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Superb8 reviews5
Sail under the spectacular Golden Gate Bridge, and view the Marin Headlands, Alcatraz and the SF sky....
Private Tour
San Diego Half-Day Marine Wildlife Tour with Lunch
Experience an exciting adventure while sailing along the San Diego coastline. Venture off into the Pacific Ocean and catch a chance to see local marine wildlife in its natural habitat, including sea lions, pelicans, and migrator... More
Private Tour

San Diego Half-Day Marine Wildlife Tour with Lunch
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USA
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Superb27 reviews4.8
Experience an exciting adventure while sailing along the San Diego coastline. Venture off into the P....
Private Tour
Brunch Cruise with Buffet in Washington
Come sailing on Seattle’s Tall Ship, a historic 19th-century style gaff-rigged schooner. We offer three public sailing tours daily from Seattle’s downtown waterfront. Our beautiful sailing ship, the Bay Lady, evokes the romanc... More
Private Tour

Brunch Cruise with Buffet in Washington
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USA
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Very Good10 reviews4
Come sailing on Seattle’s Tall Ship, a historic 19th-century style gaff-rigged schooner. We offer ....
Private Tour