Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 687 Sailing Trips activities in North America. Sort by Popularity. - Page 7Mexico City: Xochimilco at sunrise + Breakfast and transportation
Navigating through the channels of Xochimilco while the sun rises behind living volcanoes is an activity that can only be experienced in Xochimilco Mexico, and doing it by experts committed to sustainability and history makes it a... More

Mexico City: Xochimilco at sunrise + Breakfast and transportation
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North America
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Superb65 reviews5
Navigating through the channels of Xochimilco while the sun rises behind living volcanoes is an acti....
Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar
*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting from our crew who will provide you with unmatched service throughout the excursion. *Take a moment for a photo opportunity with y... More

Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open....
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North America
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Superb63 reviews4.7
*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting ....
Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience
Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own private catamaran. Complete with a professional captain & crew , your group will enjoy spacious accommodations and a premium, pers... More
Private Tour

Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience
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North America
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Superb509 reviews5
Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own ....
Private Tour
Afternoon Sail & Snorkel to the Captain Cook Monument
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adve... More
Private Tour

Afternoon Sail & Snorkel to the Captain Cook Monument
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North America
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Superb223 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....
Private Tour
Pau Hana Sunset Cocktail Cruise
Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed catamaran. This cruise includes unlimited soft drinks, tropical juices, beers, wines, cocktails and a variety of appetizers.. Great f... More
Private Tour

Pau Hana Sunset Cocktail Cruise
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North America
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Superb48 reviews4.8
Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed cat....
Private Tour
Molokini Snorkel and Performance Sail from Ma'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

Molokini Snorkel and Performance Sail from Ma'alaea Harbor
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North America
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Superb198 reviews4.9
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
Private Tour

Polynesian Canoe Sunset Sail
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More
Free Cancellation
Private Tour
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Polynesian Canoe Sunset Sail
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North America
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Superb118 reviews4.9
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Free Cancellation
Private Tour
(Saving 10% )
Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres
Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a delicious drink and the entertainment from the crew. Unique and quality service is our priority. We are sure that you will love all... More
Private Tour

Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres
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North America
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Exellent286 reviews4.4
Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a d....
Private Tour
Visit Private Beaches around Puerto Vallarta in a Private Yacht
Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours don’t go. Also enjoy the explanation from our captain on the art of sailing. This is not a boat trip, this is an experience to enj... More
Private Tour

Visit Private Beaches around Puerto Vallarta in a Private Yacht
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North America
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Superb81 reviews5
Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours do....
Private Tour
Mangrove Kayak + Snorkel & Sunset Sail hosted by Honest Eco
I founded and own HONEST ECO. With Kentucky bluegrass roots and a B.S. in Biology, I found a world with a blue sea too alluring to ignore. I arrived to Key West in 2005. Now I have 10+ years of experience studying Biology and bein... More
Private Tour

Mangrove Kayak + Snorkel & Sunset Sail hosted by Honest Eco
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North America
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Superb150 reviews5
I founded and own HONEST ECO. With Kentucky bluegrass roots and a B.S. in Biology, I found a world w....
Private Tour
Sailing Tour through the Lagoon of the 7 Colors
Sail with people who share your passion for adventure! You will explore fascinating places along the lagoon of the 7 colors. Our small groups guarantee you excellent attention and service from our crew. Disconnect from the world ... More
Private Tour

Sailing Tour through the Lagoon of the 7 Colors
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North America
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Superb996 reviews4.9
Sail with people who share your passion for adventure! You will explore fascinating places along the....
Private Tour
Sightseeing Day Sail around Boston Harbor
Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail past the seaport district, Castle... More
Private Tour

Sightseeing Day Sail around Boston Harbor
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North America
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Superb382 reviews4.7
Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner....
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

Sailing Charters in Wilmington
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North America
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Superb145 reviews5
After a successful first season I am happy to be here for back to back seasons. Sail in style on the....
Private Tour
Windjammer Classic Sunset Sail from Camden, Maine
Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. She is a modern windjammer with luxurious accommodations and plent... More
Private Tour

Windjammer Classic Sunset Sail from Camden, Maine
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North America
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Superb332 reviews4.9
Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....
Private Tour
Sailing Tour through the Laguna de los Siete Colores
Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, being your best option to know this magical place without damaging the ecosystem. Guided by a team of professionals, with whom you ... More
Private Tour

Sailing Tour through the Laguna de los Siete Colores
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North America
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Superb1,324 reviews5
Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, b....
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. We wi... More
Private Tour

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
2.5-hour Guided Sailboat Tour
2.5 hour sails for 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's Island and M... More
Private Tour

2.5-hour Guided Sailboat Tour
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North America
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Superb164 reviews4.9
2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, ....
Private Tour
Reef Snorkel, underwater adventure in Puerto Morelos With Transportation & Lunch
Snorkel activity in a caribbean reef. Amazing sightseeing and shore excursion. This is consider a must activity in Cancun. You will visit one of the most bigger reef in the world, this is consider as the 2nd one worldwide. Imagi... More
Private Tour

Reef Snorkel, underwater adventure in Puerto Morelos With Transpo....
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North America
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Very Good3 reviews4
Snorkel activity in a caribbean reef. Amazing sightseeing and shore excursion. This is consider a mu....
Private Tour
Suncoast Sailing's Sunset Sailing Experience!
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Treasure Island, Florida! You’ll set sail about an hour before sunset to give you plenty of time to catch the full range of hues p... More
Private Tour

Suncoast Sailing's Sunset Sailing Experience!
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North America
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Superb220 reviews4.9
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Tre....
Private Tour
Luxury Catamaran Sailing Charters in Maine
Sail in luxury on a 44-ft catamaran yacht! We are one of the only sailing catamaran charters in Maine, and our luxurious yacht makes for a relaxing and fun experience. Our catamaran is stable and does not bounce in waves, providin... More
Private Tour

Luxury Catamaran Sailing Charters in Maine
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North America
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Superb85 reviews4.9
Sail in luxury on a 44-ft catamaran yacht! We are one of the only sailing catamaran charters in Main....
Private Tour