Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 3Toronto Tall Ship Boat Cruise
This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the historic 'Tall Ship Kajama,' a traditional 165-foot, 3-masted schooner boat, and sit back and relax with a cold drink from the bar or order fr... More
Toronto Tall Ship Boat Cruise
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North America
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Exellent737 reviews4.3
This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the historic 'Ta....
Sunset Sailing Cruise on a Tall Ship in Boston Harbor
If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise on a classic Boston tall ship! We depart Fan Pier Marina and raise the sails, then it’s time to just chill out and relax. Get a... More
Sunset Sailing Cruise on a Tall Ship in Boston Harbor
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North America
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Superb488 reviews4.6
If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise....
Tall Ship Silva Sailing Cruise Ft. a Live Musician
A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Halifax Harbour. Join us on our comfortable and thoroughly impressive vessel for this relaxing afternoon outing on the water. Your j... More
Likely to Sell Out Tall Ship Silva Sailing Cruise Ft. a Live Musician
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North America
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Exellent348 reviews4.3
A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Ha....
St. Augustine Live Music Sail with Drinks & Sunset Option
Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience! Opt for a two-hour live music sunset sail with all sails raised, or unwind on a 90-minute After Dark Live Music Cruise (no sailin... More
Likely to Sell Out St. Augustine Live Music Sail with Drinks & Sunset Option
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North America
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Superb399 reviews4.7
Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience!....
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985... More
Likely to Sell Out Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
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North America
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Superb997 reviews4.9
2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....
Turtles & Tacos Luxury Catamaran Snorkel
Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and snorkel alongside Hawaiian green sea turtles and colorful tropical fish at ... More
Likely to Sell Out Turtles & Tacos Luxury Catamaran Snorkel
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North America
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Superb153 reviews4.7
Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....
Dolphin Sunset Cruise in Panama City Beach on the "Island Time"
The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in Panama City Beach, FL. Enjoy a rum punch while cruising along the beautiful Gulf Coa... More
Likely to Sell Out Dolphin Sunset Cruise in Panama City Beach on the "Island Time"
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North America
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Superb2,091 reviews4.9
The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which....
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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Superb246 reviews4.9
Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience ....
Halifax Sunset Cruise Ft. a Live Musician
Experience golden hour, that magical time of night when the sun makes its way below the horizon, on the Halifax Sunset Cruise aboard our signature ship, the Tall Ship Silva. Purchase wine, beer, cocktails, and other beverages from... More
Likely to Sell Out Halifax Sunset Cruise Ft. a Live Musician
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North America
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Superb85 reviews4.6
Experience golden hour, that magical time of night when the sun makes its way below the horizon, on ....
Likely to Sell Out
Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More
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Likely to Sell Out Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed
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North America
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Superb2,132 reviews4.7
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....
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Snorkel Sail Adventure off Ka'anapali Beach in Maui
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buff... More
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Likely to Sell Out Snorkel Sail Adventure off Ka'anapali Beach in Maui
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North America
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Superb49 reviews5
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....
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Key West Afternoon Reef Snorkeling with Open Bar
Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key West living reef where you will see coral and tropical fish. All snorkeling equipment is provided an... More
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Likely to Sell Out Key West Afternoon Reef Snorkeling with Open Bar
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North America
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Exellent479 reviews4.5
Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....
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Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More
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Likely to Sell Out Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
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North America
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Superb200 reviews4.7
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....
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Waikiki Turtle Snorkel and Sail on Hawea Catamaran
Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island relaxation in one extraordinary outing. Swim among sea turtles and tropical fi... More
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Likely to Sell Out Waikiki Turtle Snorkel and Sail on Hawea Catamaran
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North America
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Superb1,767 reviews4.8
Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This pop....
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Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vess... More
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Likely to Sell Out Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
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North America
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Superb196 reviews4.7
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....
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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
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Likely to Sell Out 2.5-Hour Small-Group Catamaran Sail with Drinks
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North America
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Superb340 reviews5
Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your ....
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Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar
Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based on weather, tides, and ocean conditions. • Explore Lana... More
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Likely to Sell Out Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar
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North America
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Superb73 reviews5
Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where ....
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Newport Sightseeing Day Sailing Experience on Schooner Adirondack
See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schooner Adirondack. You'll pass by many iconic sights, bridges, lighthouses and more during this 1.5-hour experience!... More
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Likely to Sell Out Newport Sightseeing Day Sailing Experience on Schooner Adirondack
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North America
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Superb144 reviews4.9
See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schoone....
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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
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Likely to Sell Out Honolulu Sunset Sail from Kewalo Harbor Including Drinks
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North America
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Superb208 reviews4.8
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....
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Monterey Bay Whale Watching
Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey Bay Canyon, one of the largest underwater canyons in the wor... More
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Likely to Sell Out Monterey Bay Whale Watching
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North America
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Superb370 reviews4.6
Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watchi....
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