Sailing Trips in USA
Top 10 Best USA Sailing Trips
Found 431 Sailing Trips activities in USA. Sort by Popularity. - Page 9Polynesian Canoe Morning Sail
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More
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Polynesian Canoe Morning Sail
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USA
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Superb18 reviews5
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Free Cancellation
(Saving 15% )
Chicago's Fireworks Show aboard Tall Ship Windy!
Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a lei... More
Likely to Sell Out Chicago's Fireworks Show aboard Tall Ship Windy!
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USA
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Superb14 reviews4.8
Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Na....
Fort Lauderdale Sailing Charter
You Embark on an unforgettable journey starting in Fort Lauderdale on our New River also known as the “Venice of America." The New River offers a blend of natural beauty, luxurious homes, and fascinating history. Your adventure ... More
Likely to Sell Out Fort Lauderdale Sailing Charter
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USA
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Superb388 reviews5
You Embark on an unforgettable journey starting in Fort Lauderdale on our New River also known as th....
New York City Sunset Sail to the Statue of Liberty
Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic sailboat is 105-feet in length and has about 3600 square feet of sail ... More
Likely to Sell Out New York City Sunset Sail to the Statue of Liberty
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USA
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Superb66 reviews4.9
Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of B....
Likely to Sell Out Waikiki Fireworks Cocktail Cruise
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USA
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Exellent7 reviews4.4
Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a b....
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
Likely to Sell Out Private Sailing on the Miami Bay - Biscayne Bay
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USA
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Superb75 reviews4.9
Let's go Sailing! Experience Miami's Biscayne Bay aboard one of Destino Charters Beneteau stylish....
Private Tour
Seattle's Best Private Sailing Adventure on the Puget Sound BYOB!
Escape the hustle and bustle of city life and embark on an exclusive 3-hour private sailing tour in the Puget Sound. This personalized voyage is designed for up to six passengers, offering an intimate and unforgettable experience ... More
Private Tour
Likely to Sell Out Seattle's Best Private Sailing Adventure on the Puget Sound BYOB!
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USA
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Superb126 reviews5
Escape the hustle and bustle of city life and embark on an exclusive 3-hour private sailing tour in ....
Private Tour
Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goa... More
Private Tour
Likely to Sell Out Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
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USA
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Superb126 reviews4.6
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....
Private Tour
Pastries & Prosecco Aboard a Tall Ship in Boston Harbor
What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable views of the city. Your ticket includes complimentary coffee and fresh-baked pastries from the incomparable Flour Bakery + Cafe. F... More
Private Tour
Likely to Sell Out Pastries & Prosecco Aboard a Tall Ship in Boston Harbor
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USA
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Superb14 reviews5
What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable v....
Private Tour
Newport Sunset Sail on Classic Sailboat
Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailboat and see all of Newport's iconic sights from the water including histor... More
Private Tour
Likely to Sell Out Newport Sunset Sail on Classic Sailboat
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USA
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Superb42 reviews4.8
Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a ....
Private Tour
Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15
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
Private Tour
Likely to Sell Out Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15
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USA
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Exellent31 reviews4.5
Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....
Private Tour
Chicago Air and Water Show VIP Cruise or Skydeck Experience
Chicago Air and Water Show 2025 Great for friends & family! PLEASE READ CAREFULLY Experience Chicago’s Air & Water Show from the Best Seat on the Lake! 10AM SAIL: Our first sail will depart at 10am sharp. Our first event wil... More
Private Tour
Likely to Sell Out Chicago Air and Water Show VIP Cruise or Skydeck Experience
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USA
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Superb2 reviews5
Chicago Air and Water Show 2025 Great for friends & family! PLEASE READ CAREFULLY Experience Chic....
Private Tour
2.5 hr Sailboat Tour aboard Orion's Child
TripAdvisor Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel. Multiple daily sails that include a quarter day and sunset sail aboard a ... More
Private Tour
Likely to Sell Out 2.5 hr Sailboat Tour aboard Orion's Child
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USA
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Superb73 reviews5
TripAdvisor Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer t....
Private Tour
Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran
Set sail on Maui's only floating tiki bar aboard a hand-built catamaran, where sunsets and handcrafted cocktails create unforgettable memories. Enjoy a relaxing evening of island tunes, light snacks, and an open bar as you glide o... More
Private Tour
Likely to Sell Out Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran
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USA
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Superb73 reviews5
Set sail on Maui's only floating tiki bar aboard a hand-built catamaran, where sunsets and handcraft....
Private Tour
Private Sunset Catamaran Sail in Cocoa Beach
Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the bea... More
Private Tour
Likely to Sell Out Private Sunset Catamaran Sail in Cocoa Beach
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USA
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Superb73 reviews5
Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a....
Private Tour
2-Hour Private Sailboat Charter in the San Francisco Bay
Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Just kick back and celebrate your special event under the romance of sail. Private sailboat charters are a great way to celebrate you... More
Private Tour
Likely to Sell Out 2-Hour Private Sailboat Charter in the San Francisco Bay
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USA
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Superb21 reviews4.9
Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Jus....
Private Tour
Private Hilton Head Sunset Sailing Tour with Dolphin Watching
This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island - generally best conditions for sailing). During Sunset, This is generally still pretty breezy with some goo... More
Private Tour
Likely to Sell Out Private Hilton Head Sunset Sailing Tour with Dolphin Watching
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USA
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Superb118 reviews5
This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound ....
Private Tour
Private Catamaran Charter in Waikiki (1-6 Guests)
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on the front of the boat, as well as 2 small nets on the back of the boat. Not only does Hawa... More
Private Tour
Likely to Sell Out Private Catamaran Charter in Waikiki (1-6 Guests)
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USA
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Superb21 reviews5
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....
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
Likely to Sell Out 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
Private Guided Sunset and Eco Tour up to 6 Passengers
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a cooler with bottled water a... More
Private Tour
Likely to Sell Out Private Guided Sunset and Eco Tour up to 6 Passengers
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USA
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Superb74 reviews5
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....
Private Tour