Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 7Kona Tradewind Catamaran Day Sail
Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails as you glide across the water, taking in panoramic views of volcanic cliffs, sparklin... More
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Kona Tradewind Catamaran Day Sail
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North America
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Superb50 reviews4.8
Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing ca....
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Private Sailing Charter on San Diego Bay
San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural wonder aboard a beautiful sailing yacht with a knowledgeable and friendly Captain? This private charterÂ... More
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Private Sailing Charter on San Diego Bay
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North America
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Superb50 reviews4.9
San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. W....
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Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms
Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the sky transform into a palette of golden hues as the sun dips be... More
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Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms
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North America
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Superb91 reviews4.7
Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. Th....
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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
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Newport Sunset Sail on Schooner Adirondack
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North America
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Superb125 reviews4.8
Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of th....
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Luxury Sunset Sail on Serendipity Catamaran in Charleston
Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seabreeze Marina in downtown Charleston. Enjoy stunning waterfront views and local wildlife as the sun dips below the horizon. This up... More
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Luxury Sunset Sail on Serendipity Catamaran in Charleston
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North America
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Superb23 reviews5
Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seab....
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Sunset Dolphin Sail Aboard the Privateer Catamaran
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer, our 78-passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mex... More
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Sunset Dolphin Sail Aboard the Privateer Catamaran
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North America
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Superb744 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
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JFarwell Adventure Yacht Sailing in the Halifax Harbour
Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the water, and offers a great introduction to sailing. Guests are encouraged to be as hands on with the sailing process as they would... More
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JFarwell Adventure Yacht Sailing in the Halifax Harbour
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North America
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Superb156 reviews5
Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the....
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Daytime Sailing Along San Diego's Skyline
Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor Sunroad Marina on Harbor Island on San Diego Bay, we often s... More
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Likely to Sell Out Daytime Sailing Along San Diego's Skyline
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North America
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Superb157 reviews4.9
Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....
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Beach Island Shelling Cruise to Keewaydin Island Tour
Enjoy a family favorite cruise aboard the Sweet Liberty, a 53' sailing catamaran, that can accommodate up to 44 passengers. Cruise along the Gordon River in Naples Bay and head out to Keewaydin Island, a 7-mile barrier island, wit... More
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Likely to Sell Out Beach Island Shelling Cruise to Keewaydin Island Tour
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North America
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Superb93 reviews4.9
Enjoy a family favorite cruise aboard the Sweet Liberty, a 53' sailing catamaran, that can accommoda....
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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
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Likely to Sell Out Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience
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North America
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Superb664 reviews5
Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own ....
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Spectacular Sunset Sail on San Diego Bay
A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group limited to six people, local captain sharing stories, hands-on sailing, and unforgettable vistas of San Diego. Watch for playful sea lions, dolphins, a... More
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Likely to Sell Out Spectacular Sunset Sail on San Diego Bay
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North America
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Superb38 reviews5
A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group limited to six people....
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Bimini or Grand Bahama Island Day Cruise
Just a 50-mile ferry ride from Florida, the beautiful Bahamas awaits! With over 700 stunning islands, this tropical paradise is famous for white-sand beaches, crystal-clear turquoise waters, and vibrant culture. Turn your getaway ... More
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Likely to Sell Out Bimini or Grand Bahama Island Day Cruise
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North America
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Good22 reviews3.2
Just a 50-mile ferry ride from Florida, the beautiful Bahamas awaits! With over 700 stunning islands....
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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... More
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Likely to Sell Out Deluxe Sail & Snorkel to the Captain Cook Monument
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North America
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Superb482 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....
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Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More
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Likely to Sell Out Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch
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North America
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Superb222 reviews4.8
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
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Puerto Vallarta Luxury Snorkel Sail with Open Bar and Lunch
Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau sailboats, taking in breathtaking views of Puerto Vallarta’s coastline and the majestic Sierra Madre mountains. This small-group experience offers a pe... More
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Likely to Sell Out Puerto Vallarta Luxury Snorkel Sail with Open Bar and Lunch
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North America
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Superb320 reviews4.8
Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau sailboats, taking in br....
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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
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Likely to Sell Out Half-Day Luxury Sailing Experience in Tulum with Open Bar
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North America
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Exellent262 reviews4.2
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....
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Key West Sailing & Snorkeling: A Reef Adventure
Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More
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Likely to Sell Out Key West Sailing & Snorkeling: A Reef Adventure
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North America
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Superb248 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
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Classic Key West Schooner Sunset Sail with Full Open Bar
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Ke... More
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Likely to Sell Out Classic Key West Schooner Sunset Sail with Full Open Bar
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North America
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Superb265 reviews4.9
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....
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Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar
*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting from our crew who will provide you with unmatched service throughout the excursion. *Take a moment for a photo opportunity with y... More
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Likely to Sell Out Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open....
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North America
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Exellent89 reviews4.5
*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting ....
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Sunset Sailing Cruise in Monterey Bay
Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience Monterey Bay. Departing daily, 90 minutes before sunset, this dreamy 1.5-... More
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Likely to Sell Out Sunset Sailing Cruise in Monterey Bay
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North America
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Superb57 reviews4.8
Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is....
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