Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 723 Sailing Trips activities in North America. Sort by Popularity. - Page 22Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar
Admire the peaceful waters of the Caribbean Sea, aboard a classic or luxury catamaran and enjoy a spectacular day sailing to Isla Mujeres on a fun-filled experience where music, drinks and incredible views will never be lacking. ... More

Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar
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North America
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Very Good35 reviews3.7
Admire the peaceful waters of the Caribbean Sea, aboard a classic or luxury catamaran and enjoy a sp....
Brunch Cruise with Buffet in Washington
Come sailing on Seattle’s Tall Ship, a historic 19th-century style gaff-rigged schooner. We offer three public sailing tours daily from Seattle’s downtown waterfront. Our beautiful sailing ship, the Bay Lady, evokes the romanc... More

Brunch Cruise with Buffet in Washington
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North America
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Very Good10 reviews4
Come sailing on Seattle’s Tall Ship, a historic 19th-century style gaff-rigged schooner. We offer ....
Hidden Beach - Marietas Islands
Spend the day exploring and enjoying the marine life of the Marietas Islands on this 5-hour excursion, departing from Puerto Vallarta. Even those without experience can feel comfortable participating in guided snorkeling excursion... More

Hidden Beach - Marietas Islands
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North America
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Exellent42 reviews4.4
Spend the day exploring and enjoying the marine life of the Marietas Islands on this 5-hour excursio....
Monterey Private 3 - 4 Hour Whale Watching Cruise
Enjoy a 3 - 4 hour sailing cruise on the Monterey Bay. This Marine Mammal and Wildlife Safari is a private guided tour and can accommodate up to 6 people. Whale sightings are NOT guaranteed. However, this tour is designed to give... More
Private Tour

Monterey Private 3 - 4 Hour Whale Watching Cruise
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North America
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Superb2 reviews5
Enjoy a 3 - 4 hour sailing cruise on the Monterey Bay. This Marine Mammal and Wildlife Safari is a p....
Private Tour
Private Catamaran from Cancun to Isla Mujeres | For up to 40 pp
Enjoy a day sailing through the Caribbean Sea aboard on a 46 ft Catamaran. Decide if you want to go on a trip to Isla Mujeres or just sail on the bay. Snorkel and discover the natural beauty of the great reefs of Cancun. Private... More
Private Tour

Private Catamaran from Cancun to Isla Mujeres | For up to 40 pp
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North America
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Exellent67 reviews4.3
Enjoy a day sailing through the Caribbean Sea aboard on a 46 ft Catamaran. Decide if you want to go....
Private Tour
Private sailing excursions, nice spacious sailboats.
We are a new sailboat tour agency in bacalar ~ are sailboats stand out with ease access, very comfortable, 2 canopy’s to keep you protected from the elements and a 5 star crew. We provide an atmosphere for you to take over and T... More
Private Tour

Private sailing excursions, nice spacious sailboats.
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North America
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Superb24 reviews4.9
We are a new sailboat tour agency in bacalar ~ are sailboats stand out with ease access, very comfor....
Private Tour
Private Oahu Sunset Charter with Tasting and Drinks
This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people while enjoying the West Oahu Sunset on this 2.5-hour experience. There’s more than enoug... More
Private Tour

Private Oahu Sunset Charter with Tasting and Drinks
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North America
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Superb46 reviews5
This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world....
Private Tour

Private Sailing Tour of Bodega Bay
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North America
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Superb86 reviews4.8
This is a unique experience because you get to sail a 33' boat with a licensed captain. You can be i....
Private Tour

Private Catamaran Tour
Our starting point is the iconic Casa China with incredible views of the lagoon from its 360° lookout tower. Our friendly bilingual staff enlivens the tour with stories of the place and important facts about the local ecosystem. ... More
Free Cancellation
Private Tour
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Private Catamaran Tour
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North America
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Superb155 reviews5
Our starting point is the iconic Casa China with incredible views of the lagoon from its 360° looko....
Free Cancellation
Private Tour
(Saving 15% )
2-Hour Morning Sail in San Diego
Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma, San Diego Bay and the downtown waterfront. This two-hour adventure on a Catalina sailboat is limited to a maximum of six (6) gues... More
Private Tour

2-Hour Morning Sail in San Diego
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North America
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Superb26 reviews4.8
Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma,....
Private Tour
Baltimore Inner Harbor Sunset Sail on Summer Wind
Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of the skyline. Bring wine for a special experience on this Inner Harbor sunset sail. S... More
Private Tour

Baltimore Inner Harbor Sunset Sail on Summer Wind
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North America
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Superb58 reviews4.9
Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun s....
Private Tour
Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles
This 8 hour private tour includes a 5 hour custom tour of the island, and a 2.5 hour sail on a sailboat including swimming or snorkeling with turtles. You can pick and choose the stops on the island tour and go at your own pace. ... More
Private Tour

Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles
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North America
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Superb3 reviews5
This 8 hour private tour includes a 5 hour custom tour of the island, and a 2.5 hour sail on a sailb....
Private Tour
Okanagan Lake Sailing Tour from Penticton & Naramata BC
Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht into the sunny waters of Okanagan Lake. We provide hands on instruction and lots of opportunities to learn or just relax. And it is ... More
Private Tour

Okanagan Lake Sailing Tour from Penticton & Naramata BC
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North America
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Superb48 reviews5
Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht int....
Private Tour
Deluxe Catamaran to Isla Mujeres, with Drinks, Snorkel & Buffet
Get ready to venture into a fantastic experience aboard our catamaran to Isla Mujeres. You will board the catamaran and we will begin our tour together with our guides and entertainers so that you have a pleasant time. You can as... More
Private Tour

Deluxe Catamaran to Isla Mujeres, with Drinks, Snorkel & Buffet
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North America
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Good22 reviews3.4
Get ready to venture into a fantastic experience aboard our catamaran to Isla Mujeres. You will boa....
Private Tour
Luxury Cruise with Dinner and Music in Los Cabos
Los Cabos offers unforgettable experiences and one not to be missed is to visit the famous Arch of Cabo San Lucas and to enjoy a sunset cruise. There are many similar options that offers this tour, but a few are unique and offers ... More
Private Tour

Luxury Cruise with Dinner and Music in Los Cabos
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North America
Los Cabos offers unforgettable experiences and one not to be missed is to visit the famous Arch of C....
Private Tour
2 hours - Private Sunset Sail along Historic Bay Front
We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to assist in making your experience a wonder memory. This 2-hour sail gives passengers a ... More
Private Tour

2 hours - Private Sunset Sail along Historic Bay Front
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North America
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Superb29 reviews4.9
We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our sta....
Private Tour
Key West Dolphin Watch and Sunset Sail on Catamaran
Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of wind. This tour is perfect for all ages and offers a wide-open, unob... More
Private Tour

Key West Dolphin Watch and Sunset Sail on Catamaran
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North America
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Superb25 reviews4.7
Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lig....
Private Tour
Private 90-Minute Harbor Sailing Charter in Key West
Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida Keys and view the city from the water in peace and tranquility. You may even get to see some fri... More
Private Tour

Private 90-Minute Harbor Sailing Charter in Key West
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North America
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Superb17 reviews4.9
Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-mi....
Private Tour
Private Boat Charter to Johns Pass, Shell Key and Egmont Key
The sunset cruise is a nice 3 hour tour to Pass A Grille after cruising around for a few hours, see the most beautiful sunset this side of the state! Bring your drinks and your cameras and make some lifetime memories. ... More
Private Tour

Private Boat Charter to Johns Pass, Shell Key and Egmont Key
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North America
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Superb3 reviews5
The sunset cruise is a nice 3 hour tour to Pass A Grille after cruising around for a few hours, see ....
Private Tour
Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound
Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these waters back in 1792. From Seattle’s Shilshole Bay Marina we sail west across Puget Sound toward the magnificent Olympic Mountains. A... More
Private Tour

Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound
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North America
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Superb23 reviews5
Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these wate....
Private Tour