Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 712 Sailing Trips activities in North America. Sort by Popularity. - Page 9The Boat People Cruise Private Harbor Cruises
Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We strive to create an unforgettable evening with contagious laughter and panoramic views of the Newport Bay. Bring your plus one or ... More
The Boat People Cruise Private Harbor Cruises
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North America
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Superb42 reviews5
Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We ....
Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor since 2012, our sailing yachts are the highest quality and operated ... More
Private Tour
Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique
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North America
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Superb32 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour
Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport
Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and family to see all the iconic waterfront sights of Newport and Narraganset... More
Private Tour
Likely to Sell Out Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport
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North America
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Superb40 reviews4.8
Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard ....
Private Tour
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
Private Tour
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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Superb80 reviews4.9
Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at ....
Private Tour
Cozumel Private Snorkeling and Charter Experience
We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On this tour, you'll have your own completely private charter visiting the famous 'El Cielo' and other amazing destinations to give you... More
Private Tour
Likely to Sell Out Cozumel Private Snorkeling and Charter Experience
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North America
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Superb25 reviews5
We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On th....
Private Tour
America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head
Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by the famous Dennis Connor. All trips take place under full sail. We only use our motor to get in a... More
Private Tour
Likely to Sell Out America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head
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North America
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Superb504 reviews4.6
Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, S....
Private Tour
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
Private Tour
Likely to Sell Out Halifax Sunset Cruise Ft. a Live Musician
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North America
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Superb47 reviews4.7
Experience golden hour, that magical time of night when the sun makes its way below the horizon, on ....
Private Tour
Catamaran Cruise from Costa Mujeres with Snorkeling and Lunch
Enjoy the cool ocean breeze and the sparkling turquoise sea as you cruise along the Mexican Caribbean on our spacious catamaran. With music, drinks, and a lively host to keep the good vibes going, this isn’t just a tour — it... More
Private Tour
Likely to Sell Out Catamaran Cruise from Costa Mujeres with Snorkeling and Lunch
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North America
Enjoy the cool ocean breeze and the sparkling turquoise sea as you cruise along the Mexican Caribbea....
Private Tour
Deluxe Day Sail in San Diego
Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego Bay offer a perfect blend of adventure and relaxation. With our passionate and kno... More
Private Tour
Likely to Sell Out Deluxe Day Sail in San Diego
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North America
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Superb56 reviews5
Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our person....
Private Tour
4-Hour St. Pete Pier to Egmont Key Experience by Ferry
From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stunning Sunshine Skyway bridge and perhaps see a dolphin or two! This is the only charter offering service from downtown St. Petersb... More
Private Tour
Likely to Sell Out 4-Hour St. Pete Pier to Egmont Key Experience by Ferry
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North America
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Superb303 reviews4.7
From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stu....
Private Tour
Key West Day Sail on Schooner America 2.0 with 2 Drinks
Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that won the first America's Cup Race in 1851. Admire her beauty on the clear, calm Caribbean... More
Private Tour
Likely to Sell Out Key West Day Sail on Schooner America 2.0 with 2 Drinks
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North America
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Superb188 reviews4.9
Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a ....
Private Tour
Private sailing tour of Bacalar Lagoon
Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper you. During the tour, you can enjoy a delicious fruit cocktail, water and beer. Our certified guides will make this tour an unfo... More
Private Tour
Likely to Sell Out Private sailing tour of Bacalar Lagoon
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North America
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Superb375 reviews5
Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper ....
Private Tour
Sail 4hr in the most SECRET Spot of Bacalar and Beach Club.
WELCOME to Mayan Paradise We are Liz (Biologist) and Danny (Sustainable Sailing) and we will guide you on this wonderful route created for you and your companions (Adventure Tourism, Nature and more). You are looking for TRANQUI... More
Private Tour
Likely to Sell Out Sail 4hr in the most SECRET Spot of Bacalar and Beach Club.
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North America
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Superb36 reviews5
WELCOME to Mayan Paradise We are Liz (Biologist) and Danny (Sustainable Sailing) and we will guide ....
Private Tour
Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall. Now operating from Ma'alaea Harbor, we invite you to join our cap... More
Private Tour
Likely to Sell Out Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran
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North America
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Superb82 reviews4.8
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....
Private Tour
Day Sailing Adventure in the Florida Marine Sanctuary
Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay”. Choose our popular 3-hour Day Sail through the Florida Keys Marine Sanctuary in Marathon, Florida. Our sailboat rides feature ... More
Private Tour
Likely to Sell Out Day Sailing Adventure in the Florida Marine Sanctuary
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North America
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Superb27 reviews5
Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay....
Private Tour
2.5 hr Sailboat Tour aboard Orion's Child
TripAdvisor Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel. Multiple daily sails that include a quarter day and sunset sail aboard a ... More
Private Tour
Likely to Sell Out 2.5 hr Sailboat Tour aboard Orion's Child
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North America
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Superb64 reviews5
TripAdvisor Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer t....
Private Tour
Afternoon Half-Day Catmaran Sailing and Snorkel Adventure
Want to enjoy a sailing tour, where you can snorkel and visit Isla Mujeres in just half a day? This is the tour for you! Enjoy sailing in one of our Catamarans and we will ensure that you enjoy your afternoon to the maximum. The t... More
Private Tour
Likely to Sell Out Afternoon Half-Day Catmaran Sailing and Snorkel Adventure
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North America
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Exellent70 reviews4.5
Want to enjoy a sailing tour, where you can snorkel and visit Isla Mujeres in just half a day? This ....
Private Tour
Sailing Charters in Wilmington
After a successful first season I am happy to be here for back to back seasons. Sail in style on the historic Wilmington river walk. Enjoy a personalized Charter experience with up to six guests. Very few sailboats are up for publ... More
Private Tour
Likely to Sell Out Sailing Charters in Wilmington
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North America
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Superb185 reviews5
After a successful first season I am happy to be here for back to back seasons. Sail in style on the....
Private Tour
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu
Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from December-March, of course, the annual humpback whales!... More
Private Tour
Likely to Sell Out Waikiki Sunset Cruise Catamaran Boat Tour on Oahu
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North America
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Superb17 reviews4.7
Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē....
Private Tour
Molokini Snorkel and Performance Sail: Mā’alaea Harbor
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
Private Tour
Likely to Sell Out Molokini Snorkel and Performance Sail: Mā’alaea Harbor
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North America
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Superb211 reviews4.8
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
Private Tour