Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 5Casco Bay Morning Windjammer Sail
Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. (NOTE: This is NOT a ... More
Casco Bay Morning Windjammer Sail
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North America
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Superb39 reviews4.9
Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the per....
Snorkel with Manta Rays Guaranteed
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More
Snorkel with Manta Rays Guaranteed
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North America
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Superb757 reviews4.8
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....
Paragon Lahaina Sunset Sail
Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the glassy, miraculous ‘au’au Channel is like floating inside an infinite ... More
Paragon Lahaina Sunset Sail
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North America
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Superb30 reviews4.9
Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from L....
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
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North America
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Superb761 reviews4.6
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....
Deluxe Sail & Snorkel to the Captain Cook Monument
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters a... More
Deluxe Sail & Snorkel to the Captain Cook Monument
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North America
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Superb576 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....
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
New York City Sunset Sail to the Statue of Liberty
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North America
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Superb75 reviews4.8
Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of B....
2-Hour Private Sailing Experience in San Diego Bay
Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing to obtain in today's world. With all the stress life brings we are happy to provide a peacefu... More
Private Tour
2-Hour Private Sailing Experience in San Diego Bay
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North America
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Superb179 reviews5
Our unique sail displays a peace sign because that is exactly what we share with our customers, peac....
Private Tour
Key West's Favorite Afternoon Dolphin Sail
Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! Enjoy sailing aboard a 60' catamaran to the dolphin playground to view wild dolphins play and frolic in their natural habitat. Atla... More
Private Tour
Key West's Favorite Afternoon Dolphin Sail
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North America
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Superb214 reviews4.6
Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....
Private Tour
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that... More
Private Tour
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali
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North America
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Superb31 reviews4.9
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....
Private Tour
Half-Day Deluxe Molokini Snorkel Excursion in Maui
Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical fish and coral reefs. Your adventure continues with a second snorkel... More
Private Tour
Half-Day Deluxe Molokini Snorkel Excursion in Maui
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North America
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Superb130 reviews4.9
Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....
Private Tour
El Cielo Snorkel by Private Boat
- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and coral formations - Stop over at a secluded pristine white sandy beach away from the crowds - Taste a delicious fish ceviche and co... More
Private Tour
El Cielo Snorkel by Private Boat
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North America
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Superb370 reviews4.8
- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and co....
Private Tour
Sunset Sail in Key West with Beverages Included
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the... More
Private Tour
Sunset Sail in Key West with Beverages Included
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North America
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Superb983 reviews4.9
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....
Private Tour
Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar
Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This romantic sunset cruise on Cabo San Lucas Bay includes unlimited drinks from an open bar, accompanied by a delightful menu of small b... More
Private Tour
Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar
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North America
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Superb2,408 reviews4.8
Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This ro....
Private Tour
Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor
Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, socialize with friends and family and take in the spectacular Maui sunset.... More
Private Tour
Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor
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North America
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Exellent24 reviews4.5
Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, ....
Private Tour
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More
Private Tour
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
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North America
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Superb317 reviews4.8
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....
Private Tour
Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger
The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk like a pirate then climb aboard the Black Sparrow and set sail in search of treasure! But wait it's no... More
Private Tour
Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger
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North America
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Superb729 reviews4.9
The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos.....
Private Tour
Private Luxury Yacht Charters, BYOB & Dolphins
We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the water on one of our sailboats. We offer hourly, daily, or customized tours according to you... More
Private Tour
Private Luxury Yacht Charters, BYOB & Dolphins
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North America
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Superb424 reviews5
We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the....
Private Tour
Top Rated San Diego Sunset Sail Classic Yacht 6 Guests
Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with Captain Phil, a USCG-licensed captain with 55 years of sailing experience. ... More
Private Tour
Top Rated San Diego Sunset Sail Classic Yacht 6 Guests
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North America
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Superb358 reviews4.9
Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San ....
Private Tour
Vancouver Sailing Experience on a 50 Foot Sailboat
I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for 20 of those, have extensive sailing and local knowledge, 12 years experience volunteering... More
Private Tour
Vancouver Sailing Experience on a 50 Foot Sailboat
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North America
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Superb112 reviews5
I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over ....
Private Tour
2-Hour Sunset Sail on the San Francisco Bay
Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous traditional vessel to take in the sights at the most bewitching time of d... More
Private Tour
2-Hour Sunset Sail on the San Francisco Bay
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North America
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Superb424 reviews4.7
Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....
Private Tour