Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 756 Sailing Trips activities in North America. Sort by Popularity. - Page 17Open Bar Boat Tour to Arcos, Animas, and Quimixto
This tour combines three of the bay’s most iconic locations in one all-inclusive adventure. Travelers love the balance of snorkeling, beach time, and jungle exploration—plus the comfort of a large double-deck boat with open ba... More
Open Bar Boat Tour to Arcos, Animas, and Quimixto
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North America
This tour combines three of the bay’s most iconic locations in one all-inclusive adventure. Travel....
2 Hour Sailing Adventure in Lake Michigan (up to 6 people)
Our trips are perfect for starters or advanced sailors. We offer a 2 -hour sailing trip overlooking views of the city of Racine and on clear day views of Milwaukee and Kenosha You can lay back and relax to the sounds of the wave... More
Private Tour
2 Hour Sailing Adventure in Lake Michigan (up to 6 people)
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North America
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Superb9 reviews5
Our trips are perfect for starters or advanced sailors. We offer a 2 -hour sailing trip overlooking ....
Private Tour
Vintage Yacht Experience Small Group 6 passengers maximum
Skip the crowded boats and enjoy a quiet, small-group sail with just six guests onboard. Sail San Diego Bay with Captain Phil—a fun, easy going captain with decades of experience—aboard his classic yacht "Liberty". Enjoy craft... More
Private Tour
Likely to Sell Out Vintage Yacht Experience Small Group 6 passengers maximum
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North America
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Superb81 reviews5
Skip the crowded boats and enjoy a quiet, small-group sail with just six guests onboard. Sail San Di....
Private Tour
Schooner Applejack Sunset Sail Tour in Boothbay Harbor
Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we... More
Private Tour
Likely to Sell Out Schooner Applejack Sunset Sail Tour in Boothbay Harbor
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North America
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Superb42 reviews4.9
Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....
Private Tour
Tiki Pub Glow Party Cruise (Adults only)
Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, sipping on your BYOB drinks. Experience the magic of the moonlit waters, paired with tunes and laughter. Join us for the most memora... More
Private Tour
Likely to Sell Out Tiki Pub Glow Party Cruise (Adults only)
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North America
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Superb16 reviews4.9
Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, si....
Private Tour
Likely to Sell Out
Adults-Only Sunset Catamaran Cruise to Isla Mujeres
Adults-Only Atmosphere Unlike typical family catamaran tours, this is exclusively for adults, creating a relaxed yet lively vibe perfect for couples, friends, and groups looking to unwind or celebrate. Stylish, Spacious Catamaran... More
Free Cancellation
Private Tour
(Saving 10% )
Likely to Sell Out Adults-Only Sunset Catamaran Cruise to Isla Mujeres
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North America
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Superb16 reviews4.9
Adults-Only Atmosphere Unlike typical family catamaran tours, this is exclusively for adults, creati....
Free Cancellation
Private Tour
(Saving 10% )
Likely to Sell Out
Speedboat and Snorkeling Adventure in Cancun
Pack your day with exciting water adventures in the vibrant Cancun jungle. Begin with a thrilling speedboat ride across the stunning Nichupte Lagoon. After the rush, ease into tranquility as you snorkel among the mesmerizing under... More
Free Cancellation
Private Tour
(Saving 20% )
Likely to Sell Out Speedboat and Snorkeling Adventure in Cancun
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North America
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Superb16 reviews4.9
Pack your day with exciting water adventures in the vibrant Cancun jungle. Begin with a thrilling sp....
Free Cancellation
Private Tour
(Saving 20% )
JFarwell Moonlight Yacht Cruise from Halifax Waterfront
Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the Captain and passengers for a social sail - or laying on the bow relaxing under the stars, this moonlight sail is ultimate freedom! ... More
Private Tour
Likely to Sell Out JFarwell Moonlight Yacht Cruise from Halifax Waterfront
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North America
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Superb48 reviews4.8
Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the C....
Private Tour
Likely to Sell Out
Isla Mujeres Catamaran Tour with Snorkeling Spinnaker and Lunch
Discover the beauty of Isla Mujeres on this 7-hour catamaran adventure from Cancun. Sail the vibrant Caribbean waters while snorkeling in a stunning reef, then take to the skies with a thrilling spinnaker ride. Once you reach Isla... More
Free Cancellation
Private Tour
(Saving 20% )
Likely to Sell Out Isla Mujeres Catamaran Tour with Snorkeling Spinnaker and Lunch
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North America
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Superb48 reviews4.8
Discover the beauty of Isla Mujeres on this 7-hour catamaran adventure from Cancun. Sail the vibrant....
Free Cancellation
Private Tour
(Saving 20% )
Full Day Luxury Catamaran Charter
Spend a full day exploring Tampa Bay aboard a private luxury catamaran! Swim, snorkel, and paddle at hidden islands like Egmont Key and Fort De Soto. Enjoy onboard charcuterie, a champagne or wine toast, and full crew service for ... More
Private Tour
Likely to Sell Out Full Day Luxury Catamaran Charter
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North America
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Superb48 reviews4.8
Spend a full day exploring Tampa Bay aboard a private luxury catamaran! Swim, snorkel, and paddle at....
Private Tour
Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar
Cruise aboard a private sailboat for just you and your group into the Sea of Cortes. Enjoy great photo opportunities as you pass by the famous Arch, Land's end, and Sea Lion Colony before you head out of the bay. Visit a secl... More
Private Tour
Likely to Sell Out Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Ba....
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North America
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Superb383 reviews4.9
Cruise aboard a private sailboat for just you and your group into the Sea of Cortes. Enjoy great ph....
Private Tour
Polynesian Canoe Sunset Sail
Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and bec... More
Private Tour
Likely to Sell Out Polynesian Canoe Sunset Sail
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North America
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Superb126 reviews4.9
Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) off....
Private Tour
Fun Boat Rental with Captain in Miami Beach - up to 6 people
Upon agreeing to embark on this adventure with us, you'll formalize the arrangement through a straightforward bareboat charter. Now, let's talk logistics. The captain's compensation is a separate matter, settled directly at the ... More
Private Tour
Likely to Sell Out Fun Boat Rental with Captain in Miami Beach - up to 6 people
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North America
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Superb53 reviews4.9
Upon agreeing to embark on this adventure with us, you'll formalize the arrangement through a straig....
Private Tour
America's Cup Evening Sailing Adventure Newport, RI
Get on board for the best hands-on sailing experience Newport, RI has to offer. A 2 hour sail around Narragansett Bay passed many iconic sights including New York Yacht Club, Ida Lewis Light, Fort Adams, Eisenhower House, Hammersm... More
Private Tour
Likely to Sell Out America's Cup Evening Sailing Adventure Newport, RI
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North America
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Superb28 reviews4.9
Get on board for the best hands-on sailing experience Newport, RI has to offer. A 2 hour sail around....
Private Tour
Key West Nighttime Full Moon Sail
Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or an evening out with family and friends. Departing in the evening as the moo... More
Private Tour
Likely to Sell Out Key West Nighttime Full Moon Sail
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North America
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Superb8 reviews5
Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1....
Private Tour
Cabo Blast Sunset Cruise: Iconic Views, Group Joy, Food and Drink
What Makes This Tour Unique? This isn’t just another sunset cruise—it’s the Cabo experience travelers dream about. You’ll sail right up to the legendary Arch, capturing postcard‑perfect photos as the colors of the sky s... More
Private Tour
Likely to Sell Out Cabo Blast Sunset Cruise: Iconic Views, Group Joy, Food and Drink
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North America
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Superb8 reviews5
What Makes This Tour Unique? This isn’t just another sunset cruise—it’s the Cabo experience t....
Private Tour
Harbor Sail Aboard the Tall Ship Denis Sullivan
Set sail on the magnificent tall ship Denis Sullivan, a Great Lakes schooner offering a unique opportunity to connect with the sea. Whether you choose to help the crew raise the sails or simply soak in the stunning views, this pub... More
Private Tour
Likely to Sell Out Harbor Sail Aboard the Tall Ship Denis Sullivan
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North America
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Superb8 reviews5
Set sail on the magnificent tall ship Denis Sullivan, a Great Lakes schooner offering a unique oppor....
Private Tour
Hawaiian Canoe Sailing Experience in Maui
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More
Private Tour
Likely to Sell Out Hawaiian Canoe Sailing Experience in Maui
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North America
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Superb60 reviews4.7
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....
Private Tour
Golden Hour Escape: Private Sunset Sail in Coastal Maine
Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the setting sun bathes the world in mesmerizing hues, crafting memories destined to endure. Set sail along Maine's exquisite coastline aboar... More
Private Tour
Likely to Sell Out Golden Hour Escape: Private Sunset Sail in Coastal Maine
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North America
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Superb20 reviews5
Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the settin....
Private Tour
Key West Sail and Snorkel Day Trip from Fort Lauderdale
Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it out for the first time! This day trip from Fort Lauderdale promises thrilling experiences and breathtaking sights both above and ... More
Private Tour
Likely to Sell Out Key West Sail and Snorkel Day Trip from Fort Lauderdale
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North America
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Good16 reviews3.1
Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it....
Private Tour