Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 23Private Luxury 42ft Sailing with Snorkeling in Los Cabos
Sail Cabo San Lucas aboard a luxurious 42 feet private sailing boat. Enjoy an unforgettable time Snorkeling with tropical fishes and cruise along the beautiful white beaches. Your yacht and crew will provide you with all the ameni... More
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Private Luxury 42ft Sailing with Snorkeling in Los Cabos
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North America
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Superb126 reviews5
Sail Cabo San Lucas aboard a luxurious 42 feet private sailing boat. Enjoy an unforgettable time Sno....
Private Tour
Private Luxury Adventure Tours in Cabo San Lucas
Want to go on Whale Watching at your own time and pace? December 15th thru April 15th, you can enjoy this amazing adventure for 2 hours departing at 09:00 am in the morning. Or you prefer more for a special day in the water that i... More
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Private Luxury Adventure Tours in Cabo San Lucas
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North America
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Superb15 reviews4.9
Want to go on Whale Watching at your own time and pace? December 15th thru April 15th, you can enjoy....
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Sailboat Cruise on Chesapeake Bay
Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay, powered only by wind! This cruise sails at 9 am, 12 Noon and 3 pm, Tuesday - Sunday and on Mondays fo... More
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Likely to Sell Out Sailboat Cruise on Chesapeake Bay
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North America
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Superb38 reviews4.8
Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides th....
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Private Sailing Charter in Brooklyn
Are you ready to set sail on a one-of-a-kind tour of New York Harbor? We've got an unforgettable adventure waiting for you! Departing from Brooklyn Bridge Park against the breathtaking backdrop of Lower Manhattan, Tantara sails s... More
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Likely to Sell Out Private Sailing Charter in Brooklyn
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North America
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Superb9 reviews5
Are you ready to set sail on a one-of-a-kind tour of New York Harbor? We've got an unforgettable adv....
Private Tour
Private Boat Snorkeling & Beach: 5 Hours + 1 Free in Vallarta
Sail on a private trip aboard our 26-foot boat. Ideal for up to 8 passengers. We are sure that with us you will know the best part of our beautiful bay of Puerto Vallarta. Do not miss the opportunity we offer you to make this rese... More
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Likely to Sell Out Private Boat Snorkeling & Beach: 5 Hours + 1 Free in Vallarta
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North America
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Superb2 reviews5
Sail on a private trip aboard our 26-foot boat. Ideal for up to 8 passengers. We are sure that with ....
Private Tour
Isla Mujeres, Snorkel, Lunch & Pick Up from Cancun to P.Morelos
Prepare for a thrilling day trip to Isla Mujeres from Cancun, tailored for nature lovers and fun-seekers with our two exciting options: Option 1: All-Inclusive Adventure We'll take you from your Cancun hotel to two incredible sno... More
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Likely to Sell Out Isla Mujeres, Snorkel, Lunch & Pick Up from Cancun to P.Morelos
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North America
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Very Good75 reviews3.7
Prepare for a thrilling day trip to Isla Mujeres from Cancun, tailored for nature lovers and fun-see....
Private Tour
Private Tour: Bacalar Lagoon Tour Sailboat or Pontoon Adventure
Experience the stunning Bacalar Lagoon like never before with my exclusive private tour. Whether you choose the elegance of a sailboat or the comfort of a pontoon boat, I’ll guide you through this mesmerizing natural wonder in a... More
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Likely to Sell Out Private Tour: Bacalar Lagoon Tour Sailboat or Pontoon Adventure
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North America
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Superb4 reviews5
Experience the stunning Bacalar Lagoon like never before with my exclusive private tour. Whether you....
Private Tour
Luxury Sailboat Tour at Sunset in Los Cabos + Snacks + Premium Drinks
Sail along the coast, enjoying the refreshing breeze in this exclusive sailing experience. Marvel at the beauty that makes Los Cabos a unique destination and enjoy this adventure aboard our luxurious French-made sailboats and cat... More
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Likely to Sell Out Luxury Sailboat Tour at Sunset in Los Cabos + Snacks + Premium Dr....
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North America
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Superb13 reviews5
Sail along the coast, enjoying the refreshing breeze in this exclusive sailing experience. Marvel a....
Free Cancellation
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(Saving 5% )
Schooner Applejack 2-Hour Day Sail from Boothbay Harbor
Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a 2hr. day sail on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we set a c... More
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Likely to Sell Out Schooner Applejack 2-Hour Day Sail from Boothbay Harbor
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North America
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Exellent35 reviews4.3
Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....
Private Tour
Private Whale Watching Sailing Tour
Amaze yourself appreciating our most awaited visitors of the year, the Humpback Whales! Book this half-day tour on a beautiful and comfortable sailboat while you enjoy the breeze , the sun and the tide while you look for whales, d... More
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Likely to Sell Out Private Whale Watching Sailing Tour
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North America
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Superb6 reviews5
Amaze yourself appreciating our most awaited visitors of the year, the Humpback Whales! Book this ha....
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2 Hour Sailing Lesson in Wrightsville Beach
Experience the thrill of sailing a 26' performance keelboat! Our knowledgeable captains will take you around the waterways of Wrightsville Beach and out into the Atlantic Ocean. You have the freedom to make this a learning experie... More
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Likely to Sell Out 2 Hour Sailing Lesson in Wrightsville Beach
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North America
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Superb8 reviews5
Experience the thrill of sailing a 26' performance keelboat! Our knowledgeable captains will take yo....
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
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Likely to Sell Out Key West Sail and Snorkel Day Trip from Fort Lauderdale
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North America
Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it....
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Private Sail New York with Brooklyn Sail (Reserve the entire boat)
2.5 hour sails for private groups up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, 159 Bridge Park Drive. Views of the Brooklyn Bridge, Statue of Liberty, World Trade Center, Ellis Island, Governor... More
Private Tour
Likely to Sell Out Private Sail New York with Brooklyn Sail (Reserve the entire boat....
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North America
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Superb125 reviews5
2.5 hour sails for private groups up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Br....
Private Tour
Likely to Sell Out Luxury Camden Sailing Experience
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North America
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Superb9 reviews5
Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Faste....
Private Tour
Portland Tall Ship Private Charter on Casco Bay
What better way to see the delights than in the style of a private charter for you and five friends or family members? Experience the beauty and serenity of the rugged coastline as you gaze upon seabirds, sea houses, and islands. ... More
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Likely to Sell Out Portland Tall Ship Private Charter on Casco Bay
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North America
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Superb9 reviews5
What better way to see the delights than in the style of a private charter for you and five friends ....
Private Tour
Private Eco-Tour on a Recreational Catamaran with Kayaks Included
Sailing Fun! Enjoy an easy and relaxing ride through the most beautiful places in the lagoon aboard a recreational catamaran. During this tour, you will swim in crystal clear waters, learn about the local flora and fauna, and enjo... More
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Likely to Sell Out Private Eco-Tour on a Recreational Catamaran with Kayaks Included
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North America
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Superb75 reviews5
Sailing Fun! Enjoy an easy and relaxing ride through the most beautiful places in the lagoon aboard ....
Private Tour
Enjoy The Spanish Galeon with a Romantic Night Dinner in Cancun
If you are visiting Cancun or Riviera Maya is time to live the most romantic experience sailing on our Columbus cruise, and live an unforgettable evening with that special someone with a dinner to choose between vegetarian, meat o... More
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Likely to Sell Out Enjoy The Spanish Galeon with a Romantic Night Dinner in Cancun
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North America
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Very Good4 reviews3.8
If you are visiting Cancun or Riviera Maya is time to live the most romantic experience sailing on o....
Private Tour
4hrs / 46ft Catamaran Private Charter From Cancun to Isla Mujeres
This catamaran has capacity up to 45 people. We provide a high quality service, nice boat and we take care of customer during the all the booking process, service and follow up after the tour is performed. Customer´s feedback is ... More
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Likely to Sell Out 4hrs / 46ft Catamaran Private Charter From Cancun to Isla Mujeres
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North America
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Superb3 reviews5
This catamaran has capacity up to 45 people. We provide a high quality service, nice boat and we tak....
Private Tour
Waikiki Private Sunset Sail Romantic and Private
Adventure Awaits aboard our Fabulous 48' private yacht. Bring along your family and friends for a spectacular Hawaiian sunset on your private yacht. Get a chance to see whales, dolphins and sea turtles. Immerse yourself in a bucke... More
Private Tour
Likely to Sell Out Waikiki Private Sunset Sail Romantic and Private
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North America
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Superb3 reviews5
Adventure Awaits aboard our Fabulous 48' private yacht. Bring along your family and friends for a sp....
Private Tour
Snorkel Adventure through the Sea of Cortez
Sail through the Sea of Cortez, a blue and shimmering spectacle around Cabo San Lucas. You will ride a luxurious and comfortable catamaran along the Cabo bays to admire the greatest landscapes of Baja. As you get immerse into Sant... More
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Likely to Sell Out Snorkel Adventure through the Sea of Cortez
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North America
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Exellent7 reviews4.4
Sail through the Sea of Cortez, a blue and shimmering spectacle around Cabo San Lucas. You will ride....
Private Tour