Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 714 Sailing Trips activities in North America. Sort by Popularity. - Page 16Lahaina Maui Midmorning Whale Watch in the Humpback Sanctuary
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More
Lahaina Maui Midmorning Whale Watch in the Humpback Sanctuary
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North America
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Good3 reviews3.3
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....
Key West Champagne Sunset Sail with Drinks and Hors d Oeuvres
Experience the magic of a Key West sunset from the water on this elegant 2-hour sailing cruise departing from the historic Key West Seaport. As the sails are raised and the breeze carries you across the sparkling Gulf waters, unwi... More
Key West Champagne Sunset Sail with Drinks and Hors d Oeuvres
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North America
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Good3 reviews3.3
Experience the magic of a Key West sunset from the water on this elegant 2-hour sailing cruise depar....
Old Plank Adventures: Sail into Deep Tranquility
Old Plank Sailing Adventures is a boutique luxury sailing charter and aquatic expedition company, delivering gourmet 5-star experiences on the sparkling waters of Santa Monica Bay and beyond. Founded by Captain & Chef Matthew Manc... More
Private Tour
Old Plank Adventures: Sail into Deep Tranquility
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North America
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Superb2 reviews5
Old Plank Sailing Adventures is a boutique luxury sailing charter and aquatic expedition company, de....
Private Tour
Original Cruisin Tikis Shark Tooth and Sea Shell Scavenger Hunt
This interactive experience is perfect for families, kids, and anyone who loves the thrill of the hunt—whether you’re spotting shark teeth, collecting shells, or simply enjoying time on the water. We provide cooler, ice, bottl... More
Private Tour
Likely to Sell Out Original Cruisin Tikis Shark Tooth and Sea Shell Scavenger Hunt
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North America
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Superb1 review5
This interactive experience is perfect for families, kids, and anyone who loves the thrill of the hu....
Private Tour
Private Sunset and Eco Tour in Destin Up to 18 Guests
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a full restroom, as well as a... More
Private Tour
Likely to Sell Out Private Sunset and Eco Tour in Destin Up to 18 Guests
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North America
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Superb44 reviews5
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....
Private Tour
2-Hour Relaxing Chesapeake Day Sail on Lady Patty
Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in the picturesque views of St. Michaels, MD. Your journey includes gliding throu... More
Private Tour
Likely to Sell Out 2-Hour Relaxing Chesapeake Day Sail on Lady Patty
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North America
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Superb28 reviews5
Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise of....
Private Tour
JFarwell Sunset Wine and Cheese Yacht Sailing
Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to invite our guests to be involved in sailing - take the helm, hoist the sails, or sit back and enjoy the beautiful sights and wines ... More
Private Tour
Likely to Sell Out JFarwell Sunset Wine and Cheese Yacht Sailing
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North America
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Superb174 reviews4.9
Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to i....
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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Superb63 reviews4.6
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....
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
Private Tour
Likely to Sell Out Snorkel Adventure through the Sea of Cortez
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North America
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Exellent10 reviews4.5
Sail through the Sea of Cortez, a blue and shimmering spectacle around Cabo San Lucas. You will ride....
Private Tour
Jungle Tour In Cancun, drive a speedboat through the lagoon
Welcome to the most enigmatic activity in Cancun, the famous jungle tour, this is the best and quick way to know Cancun and all its beauty. Here you will know the Nichupte Lagoon that is a marvelous lagoon in Mexico, here you will... More
Private Tour
Likely to Sell Out Jungle Tour In Cancun, drive a speedboat through the lagoon
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North America
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Exellent4 reviews4.3
Welcome to the most enigmatic activity in Cancun, the famous jungle tour, this is the best and quick....
Private Tour
Tapas Tasting Sailboat Experience in Houston
Enjoy a unique sailing experience with our 2-hour tapas sail in Kemah, Houston. This curated event blends the elegance of sailing with Mediterranean-inspired tapas, allowing you to savor five seasonal dishes while cruising on a cl... More
Private Tour
Likely to Sell Out Tapas Tasting Sailboat Experience in Houston
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North America
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Exellent4 reviews4.3
Enjoy a unique sailing experience with our 2-hour tapas sail in Kemah, Houston. This curated event b....
Private Tour
Sunset Sail in the Gulf of Mexico for up to 6 Guests
Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the sun dips below the horizon. For two and a half hours, enjoy the stunning views along Fort ... More
Private Tour
Likely to Sell Out Sunset Sail in the Gulf of Mexico for up to 6 Guests
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North America
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Superb11 reviews5
Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the roman....
Private Tour
2 Hours Cocktail Sail Aboard Bella
Our experienced captains will sail you to the most beautiful local spots to watch the sunset on the water. Spot dolphins, seabirds, and other wildlife as you pass by islands and marshlands. The boat is fully equipped with air con... More
Private Tour
Likely to Sell Out 2 Hours Cocktail Sail Aboard Bella
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North America
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Superb2 reviews5
Our experienced captains will sail you to the most beautiful local spots to watch the sunset on the ....
Private Tour
Afternoon Catamaran to Isla Mujeres: Snorkel, Open Bar & Sunset
This is one of the few afternoon catamaran experiences available in Cancun. Discover Isla Mujeres on a relaxed afternoon catamaran tour from Cancun. Avoid the morning crowds and enjoy snorkeling, an open bar, beach club access, a... More
Private Tour
Likely to Sell Out Afternoon Catamaran to Isla Mujeres: Snorkel, Open Bar & Sunset
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North America
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Superb1 review5
This is one of the few afternoon catamaran experiences available in Cancun. Discover Isla Mujeres o....
Private Tour
Sea Daddy Private Yacht - 50 ft
Enjoy a day cruising with friends and family on the open water, explore local scenery, and experience the beautiful Cancun weather! Charter this amazing luxury Sea Ray Flybridge combining comfort & style for up to 16 people. Cab... More
Private Tour
Likely to Sell Out Sea Daddy Private Yacht - 50 ft
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North America
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Superb1 review5
Enjoy a day cruising with friends and family on the open water, explore local scenery, and experienc....
Private Tour
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More
Private Tour
Likely to Sell Out 3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People
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North America
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Superb1 review5
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour
Likely to Sell Out
Tour Sailing 4 Hours Private Magic Bacalar Up to 7 People
We will sail in a beautiful, clean sailboat, with full safety equipment and in good condition, boat equipped with bathroom for emergencies. Surrounded by lush nature and crystal clear waters of the most beautiful lagoon in the wor... More
Free Cancellation
Private Tour
(Saving 10% )
Likely to Sell Out Tour Sailing 4 Hours Private Magic Bacalar Up to 7 People
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North America
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Superb1 review5
We will sail in a beautiful, clean sailboat, with full safety equipment and in good condition, boat ....
Free Cancellation
Private Tour
(Saving 10% )
Likely to Sell Out
Cabo Private Sunset Sailing with Open Bar and Appetizers
Unlike crowded sightseeing boats, you will enjoy a private luxury sailboat experience with personalized service and a relaxed atmosphere designed for comfort and exclusivity. The experience includes an unlimited open bar, freshly ... More
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out Cabo Private Sunset Sailing with Open Bar and Appetizers
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North America
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Superb28 reviews4.9
Unlike crowded sightseeing boats, you will enjoy a private luxury sailboat experience with personali....
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out
Private Key West Sandbar and Paddle by Boat
Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats and wildlife refuges as well as spot an abundance of marine birds and sea life. Padd... More
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out Private Key West Sandbar and Paddle by Boat
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North America
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Superb41 reviews4.9
Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may....
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out
Los Cabos Sunset Sailing Adventure
Experience a breathtaking sunset sail on the Cabo San Lucas Bay aboard a luxury catamaran, complete with delicious appetizers and an international open bar. After being picked up from your hotel, embark from the Cabo San Lucas Mar... More
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out Los Cabos Sunset Sailing Adventure
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North America
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Exellent2 reviews4.5
Experience a breathtaking sunset sail on the Cabo San Lucas Bay aboard a luxury catamaran, complete ....
Free Cancellation
Private Tour
(Saving inf% )