Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 769 Sailing Trips activities in North America. Sort by Popularity. - Page 4Sunset 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
Sunset Sail in Key West with Beverages Included
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North America
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Superb973 reviews4.9
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....
Half-Day Luxury Sailing Experience in Tulum with Open Bar
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so that makes the experience better. The snorkeling is amazing, as you will see much colorful fish, st... More
Half-Day Luxury Sailing Experience in Tulum with Open Bar
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North America
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Exellent260 reviews4.2
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views ... More
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
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North America
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Superb200 reviews4.8
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....
2.5-Hour Small-Group Catamaran Sail with Drinks
Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail. Designed for comfort and stability, these modern catamarans featu... More
2.5-Hour Small-Group Catamaran Sail with Drinks
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North America
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Superb313 reviews5
Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your ....
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
Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger
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North America
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Superb708 reviews4.9
The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos.....
Newport Sunset Sail on Schooner Adirondack
Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! 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 sailbo... More
Likely to Sell Out Newport Sunset Sail on Schooner Adirondack
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North America
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Superb120 reviews4.8
Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of th....
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More
Likely to Sell Out Four Winds Molokini Snorkeling Tour from Maalaea Harbor
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North America
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Superb844 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
Sailing on Historic Schooner Yacht in Salem, MA
Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience the majesty aboard John G. Alden's personal schooner yacht Malabar X. Winner of the 1930 and 1932 Newport to Bermuda race and open... More
Likely to Sell Out Sailing on Historic Schooner Yacht in Salem, MA
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North America
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Superb198 reviews4.9
Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience ....
Kauai’s Na Pali Coast Snorkel and Sail Tour
Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making it the top choice for fami... More
Likely to Sell Out Kauai’s Na Pali Coast Snorkel and Sail Tour
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North America
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Superb569 reviews4.8
Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour cat....
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
Likely to Sell Out 2-Hour Sunset Sail on the San Francisco Bay
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North America
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Superb418 reviews4.7
Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....
Sunset Sail Along the San Diego Skyline
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water. Our San Diego Bay Sunset Sailing Cruises provide an up-close and personal view o... More
Likely to Sell Out Sunset Sail Along the San Diego Skyline
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North America
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Superb637 reviews4.9
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....
Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant sailing experience. Guests board a spacious Fury Catamaran, part of the largest luxury fleet in the Florida Keys, and sail to North Ame... More
Likely to Sell Out Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail
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North America
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Exellent383 reviews4.4
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....
Best of Halifax Harbour Boat Tour
This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside our Captain and Deckhand throughout the relaxed harbour tour as they share Halifax's history and present day facts!... More
Likely to Sell Out Best of Halifax Harbour Boat Tour
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North America
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Superb90 reviews4.9
This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside ....
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
Likely to Sell Out Key West's Favorite Afternoon Dolphin Sail
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North America
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Superb209 reviews4.6
Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....
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
Likely to Sell Out El Cielo Snorkel by Private Boat
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North America
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Superb366 reviews4.8
- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and co....
Private Tour
Waikoloa Signature Catamaran Sunset Sail
End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers a smooth, comfortable ride with panoramic views of Mauna Kea... More
Private Tour
Likely to Sell Out Waikoloa Signature Catamaran Sunset Sail
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North America
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Superb413 reviews4.7
End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. De....
Private Tour
San Francisco Bay Sailing Cruise
Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sail away from bustling city and enjoy photo ops from the vantage point of the water. You’ll coast past the city skyline, the Gold... More
Private Tour
Likely to Sell Out San Francisco Bay Sailing Cruise
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North America
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Superb649 reviews4.9
Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sa....
Private Tour
Windjammer Classic Sunset Sail from Camden, Maine
Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. She is a modern windjammer with luxurious accommodations and plent... More
Private Tour
Likely to Sell Out Windjammer Classic Sunset Sail from Camden, Maine
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North America
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Superb456 reviews4.9
Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....
Private Tour
Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience
Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own private catamaran. Complete with a professional captain & crew , your group will enjoy spacious accommodations and a premium, pers... More
Free Cancellation
Private Tour
(Saving 5% )
Likely to Sell Out Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience
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North America
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Superb655 reviews5
Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own ....
Free Cancellation
Private Tour
(Saving 5% )
Likely to Sell Out
Small-Group San Diego Afternoon Sailing Excursion
This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five friends and fill up the whole boat!). Sit back, relax and enjoy the com... More
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out Small-Group San Diego Afternoon Sailing Excursion
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North America
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Superb556 reviews4.9
This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing....
Free Cancellation
Private Tour
(Saving inf% )