Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 723 Sailing Trips activities in North America. Sort by Popularity. - Page 25Sail away! Hobie Cat Tour Bacalar
Discover with us the breathtaking lagoon of the seven colors. We tell you the true stories of the Pirates of the Caribbean. Learn more about cenotes and stomalites and immerse yourself in the mystical world of the Maya.... More

Sail away! Hobie Cat Tour Bacalar
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North America
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Superb28 reviews5
Discover with us the breathtaking lagoon of the seven colors. We tell you the true stories of the Pi....
Private Sunrise Tour with Breakfast on Board
A unique activity in Bacalar that you won't find with anyone else. Enjoy an incredible breakfast at dawn, guided by a team of professionals who will make this adventure a magical memory.... More
Private Tour

Private Sunrise Tour with Breakfast on Board
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North America
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Superb47 reviews5
A unique activity in Bacalar that you won't find with anyone else. Enjoy an incredible breakfast at ....
Private Tour
Boat & Yacht Tour Amazing Sandbar Adventure, Water Toys & Snorkel
Enjoy the day on the water with friends and family with Dolphin Water Sport. Our +650 reviews on Google with a score of 4.9 guarantee our quality. Come aboard our Boat and Yacht to enjoy an incredible Boat Trip in Miami. We'll cr... More
Private Tour

Boat & Yacht Tour Amazing Sandbar Adventure, Water Toys & Snorkel
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North America
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Superb47 reviews5
Enjoy the day on the water with friends and family with Dolphin Water Sport. Our +650 reviews on Goo....
Private Tour
2hr. PRIVATE Sailing Experience on San Francisco Bay (6 Guests)
This is a "Private Charter" Sailing Experience on San Francisco Bay for up to 6 guests, with a USCG licensed captain and crew where you'll sail past the Golden Gate Bridge, Alcatraz and Angel Islands and across the San Francisco w... More
Private Tour

2hr. PRIVATE Sailing Experience on San Francisco Bay (6 Guests)
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North America
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Superb47 reviews5
This is a "Private Charter" Sailing Experience on San Francisco Bay for up to 6 guests, with a USCG ....
Private Tour
Afternoon Sail
Take a 2.0 hour sailing cruise on a Sparkman and Stephens Sailing Yacht. With your small-group, engage on this classic 42 ft yacht, that accommodates a 6 passenger maximum for an intimate cruise through the waters of Wrightsvill... More
Private Tour

Afternoon Sail
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North America
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Superb30 reviews5
Take a 2.0 hour sailing cruise on a Sparkman and Stephens Sailing Yacht. With your small-group, enga....
Private Tour
Luxury Sailboat at Sunset in Cancun
To cross the calm waters of the Caribbean, there is no better means of transportation than a catamaran. These specialized sailboats have multiple hulls so that sailing in them is the most pleasant. They are ideal for those looking... More
Private Tour

Luxury Sailboat at Sunset in Cancun
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North America
To cross the calm waters of the Caribbean, there is no better means of transportation than a catamar....
Private Tour
Private Sailing between Mangroves
Within the activities of this tour, it will be bird watching, sailing in an ecological way without motor. We will swim in the places with the most crystalline water. we will eat exotic local seasonal fruit. With only your group,... More
Private Tour

Private Sailing between Mangroves
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North America
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Superb137 reviews5
Within the activities of this tour, it will be bird watching, sailing in an ecological way without m....
Private Tour
Full-Day El Cielo Snorkel Tour in Cozumel with Transportation and Lunch
You will discover an underwater world. Admire the colorful variety of fish and the different forms that the coral reef has. El Cielo reef is amazing for itself, the starfish is the main attraction of this place. Observe how the ... More
Private Tour

Full-Day El Cielo Snorkel Tour in Cozumel with Transportation and....
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North America
You will discover an underwater world. Admire the colorful variety of fish and the different forms t....
Private Tour
Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village
Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the island like never before as you set sail from the only pier in W... More
Private Tour

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village
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North America
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Very Good8 reviews3.8
Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-bui....
Private Tour
Midday Whale Watch: Mā’alaea Harbor
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
Private Tour

Midday Whale Watch: Mā’alaea Harbor
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North America
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Superb100 reviews4.9
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....
Private Tour
Schooner Appledore Day Sail with Full Bar in Key West
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comf... More
Private Tour

Schooner Appledore Day Sail with Full Bar in Key West
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North America
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Superb66 reviews4.9
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....
Private Tour

Sunrise by Paddle or Kayak with Floating Picnic
Dare to live a new experience! During this activity you will connect with your ecological SELF as you paddle towards sunrise. Enjoy a delicious picnic in a natural environment while you immerse yourself in warm and crystal clear w... More
Free Cancellation
Private Tour
(Saving 10% )

Sunrise by Paddle or Kayak with Floating Picnic
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North America
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Superb307 reviews5
Dare to live a new experience! During this activity you will connect with your ecological SELF as yo....
Free Cancellation
Private Tour
(Saving 10% )
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
Private Tour

Luxury Sailboat Tour at Sunset in Los Cabos + Snacks + Premium Dr....
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North America
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Superb12 reviews5
Sail along the coast, enjoying the refreshing breeze in this exclusive sailing experience. Marvel a....
Private Tour

Half Day Sail Orcas Island
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North America
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Superb15 reviews5
Lessons are private and designed so you can brings friends and family with no extra charge. Up to 6 ....
Private Tour
The Best Catamaran Tour to Isla Mujeres from Cancún
Discover Isla Mujeres and visit one of the beutiful beaches in the world, from incredible catamaran equipped with all the comforts! Enjoy with your family and your friends a quiet ride catamaran sailing on the crystal clear waters... More
Private Tour

The Best Catamaran Tour to Isla Mujeres from Cancún
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North America
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Superb5 reviews4.8
Discover Isla Mujeres and visit one of the beutiful beaches in the world, from incredible catamaran ....
Private Tour
Afternoon Ali'i Adventure
Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. ... More
Private Tour

Afternoon Ali'i Adventure
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North America
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Superb6 reviews5
Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....
Private Tour
3 Hour Luxury Private Sailing Catamaran for 7-12 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

3 Hour Luxury Private Sailing Catamaran for 7-12 People
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North America
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Superb6 reviews5
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour
Private Catamaran Charter in Waikiki (7-12 Guests)
(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot ca... More
Private Tour

Private Catamaran Charter in Waikiki (7-12 Guests)
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North America
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Superb6 reviews5
(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....
Private Tour
Sailing Charter around Vancouver Harbour Private Tour
Your private sailing charter will offer you a unique and scenic perspective of Vancouver Harbour and its surrounding inlets. Contagious is an Oceanis 46.1 and has all the features of a large cruising Yacht with a rare balance betw... More
Private Tour

Sailing Charter around Vancouver Harbour Private Tour
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North America
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Superb2 reviews5
Your private sailing charter will offer you a unique and scenic perspective of Vancouver Harbour and....
Private Tour
Private Sailing Tour -2 Hour (Up to 12 Passengers)
Christened in 1934, Cloudia is a beautifully restored, rare example of a classic Norwegian double ended ketch. Inspired by the original designs of famed naval architect Colin Archer (1832-1921), from Larvik, Norway, the Cloudia is... More
Private Tour

Private Sailing Tour -2 Hour (Up to 12 Passengers)
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North America
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Superb2 reviews5
Christened in 1934, Cloudia is a beautifully restored, rare example of a classic Norwegian double en....
Private Tour