Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 770 Sailing Trips activities in North America. Sort by Popularity. - Page 4Sunset 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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Superb627 reviews4.9
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....
Day Sails and Sunset tours on Schooner Surprise in Camden Maine
Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at most and have cushioned seating on board for all. Experienced crew will point out wild life, tell you history of our area and show... More
Likely to Sell Out Day Sails and Sunset tours on Schooner Surprise in Camden Maine
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North America
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Superb91 reviews4.9
Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at ....
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
Likely to Sell Out Half-Day Luxury Sailing Experience in Tulum with Open Bar
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North America
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Exellent256 reviews4.2
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....
Day's End Cocktail Sunset Sail
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. This isn’t a dinner cruise, it’s happy hour reimagined (a true ‘pau hana’ at sea) with handcrafted drin... More
Likely to Sell Out Day's End Cocktail Sunset Sail
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North America
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Superb84 reviews4.7
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....
Afternoon Sail & Snorkel to the Captain Cook Monument
A three hour tour you won't want to miss! 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 a... More
Likely to Sell Out Afternoon Sail & Snorkel to the Captain Cook Monument
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North America
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Superb733 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....
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
Likely to Sell Out Sunset Sail in Key West with Beverages Included
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North America
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Superb954 reviews4.9
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....
Deluxe Sunset & Day Sail Small Group
Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as the sky transforms into a masterpiece of color. Keep an eye out for playfu... More
Likely to Sell Out Deluxe Sunset & Day Sail Small Group
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North America
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Superb291 reviews5
Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect....
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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Exellent381 reviews4.4
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....
Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef
Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quality, comfort, and performance. Live the yachting lifestyle, walk barefoot on the deck, feel the sun and breeze on your face, dance ... More
Likely to Sell Out Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef
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North America
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Exellent302 reviews4.5
Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quali....
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
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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Superb39 reviews5
Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where ....
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
Likely to Sell Out Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar
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North America
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Superb2,366 reviews4.8
Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This ro....
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
Likely to Sell Out Monterey Bay Whale Watching
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North America
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Superb330 reviews4.6
Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watchi....
Waikiki Sunset Cruise from Oahu
Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point to observe marine life such as dolphins, whales, sea... More
Likely to Sell Out Waikiki Sunset Cruise from Oahu
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North America
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Superb61 reviews4.8
Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks an....
Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village
Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the island like never before as you set sail from the only pier in W... More
Likely to Sell Out Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village
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North America
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Superb26 reviews4.6
Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-bui....
Likely to Sell Out Key West Dolphin and Snorkel Experience
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North America
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Exellent356 reviews4.4
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....
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
Likely to Sell Out Newport Sunset Sail on Classic Sailboat
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North America
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Superb44 reviews4.8
Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a ....
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
Likely to Sell Out Newport Sightseeing Day Sailing Experience on Schooner Adirondack
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North America
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Superb78 reviews4.9
See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schoone....
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
Likely to Sell Out Half-Day Deluxe Molokini Snorkel Excursion in Maui
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North America
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Superb119 reviews4.9
Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....
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
Likely to Sell Out Sunset Sailing Cruise on a Tall Ship in Boston Harbor
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North America
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Superb419 reviews4.6
If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise....
Sunset Catamaran Cruise in Ft. Lauderdale
A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach as the sun slips slowly behind the lights of the city. This evening cruise calls for sun ... More
Likely to Sell Out Sunset Catamaran Cruise in Ft. Lauderdale
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North America
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Superb701 reviews4.8
A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....