Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 674 Sailing Trips activities in North America. Sort by Popularity. - Page 34Private Sunset Sail for Two
Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise along the vibrant waterfront and marvel at the cityscape. Create a memory of a lifetime while sailing past Downtown, Point Loma, an... More
Private Tour

Private Sunset Sail for Two
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North America
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Superb5 reviews5
Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise a....
Private Tour
Adult Only - Cabo San Lucas Romantic Sunset Cruise
Finding the right for you Sunset Cruise experience can be sometimes overwhelming and more in a destination as diverse as Los Cabos. This experience offers the perfect blend of relaxation, not crowded, Adult only, laid-back fun, de... More
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Adult Only - Cabo San Lucas Romantic Sunset Cruise
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North America
Finding the right for you Sunset Cruise experience can be sometimes overwhelming and more in a desti....
Private Tour
Public Schooner Sail in Greenport
You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see the East End of Long Island, and sailing aboard our unique schooner makes the experience extra special. U... More
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Public Schooner Sail in Greenport
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North America
You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands d....
Private Tour
Aloha Wednesday Sunset Sail - All Drinks Included - Lux Catamaran
Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha Wednesday Sunset Sail. This midweek escape combines tropical charm with st... More
Private Tour

Aloha Wednesday Sunset Sail - All Drinks Included - Lux Catamaran
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North America
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Superb1 review5
Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit....
Private Tour
Private 2-Hour Wind and Wine Sunset Sail in Key West
This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from around the world and a variety of beers. You will be sailing on a 65-foot schooner while watching the sunset into the ocean. There... More
Private Tour

Private 2-Hour Wind and Wine Sunset Sail in Key West
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North America
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Superb81 reviews4.9
This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from ....
Private Tour
Private Morning Ceremony Sailing Charter
This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, and more. We offer this experience at a discounted rate to accommodate groups wanting to do private charters in the morning to celeb... More
Private Tour

Private Morning Ceremony Sailing Charter
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North America
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Superb81 reviews4.9
This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, an....
Private Tour
Early Sail with the Whales from Ma'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

Early Sail with the Whales from Ma'alaea Harbor
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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....
Private Tour
Private tour at Sea of Cortés: Sunset tour or Snorkel
We kick off our day with the best available transportation service for our clients, featuring brand-new, fully-equipped vehicles for your comfort. Upon arriving at Puerto Los Cabos Marina, our sailboat will be waiting to begin the... More
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Private tour at Sea of Cortés: Sunset tour or Snorkel
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North America
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Good3 reviews3.3
We kick off our day with the best available transportation service for our clients, featuring brand-....
Private Tour
Private Catamaran from Cancun to Isla Mujeres | For up to 100 pp
Experience the Caribbean like never before with our sophisticated seafarer guiding you through its pristine waters. During this tour, you will have one snorkel stop at any of the following places: El meco, Sac Bajo, El Farito, or... More
Private Tour

Private Catamaran from Cancun to Isla Mujeres | For up to 100 pp
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North America
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Superb12 reviews5
Experience the Caribbean like never before with our sophisticated seafarer guiding you through its p....
Private Tour
Tall Ship Sailing Tour in Chicago with Fireworks Display
Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seat in town! Grab a cool drink from our bar, relax, and enjoy a leisurely... More
Private Tour

Tall Ship Sailing Tour in Chicago with Fireworks Display
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North America
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Superb12 reviews5
Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Na....
Private Tour
Private Sailing Adventure in Bacalar
Join us on an exciting sailing adventure. Learn about the Lagoon and the art of moving with wind. We explore mangroves, shoreline and Cenotes. Our guides are knowledgeable about the area, each point we visit comes with a detail ex... More
Private Tour

Private Sailing Adventure in Bacalar
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North America
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Superb12 reviews5
Join us on an exciting sailing adventure. Learn about the Lagoon and the art of moving with wind. We....
Private Tour
Basic Catamaran to Isla Mujeres from Cancun
Oceanix Isla Mujeres Essential Tour, a 6-hour trip full of fun, relaxation and unforgettable moments in the stunning Mexican Caribbean. Designed for those looking for the perfect combination of sailing excitement, unlimited drinks... More
Private Tour

Basic Catamaran to Isla Mujeres from Cancun
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North America
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Superb12 reviews5
Oceanix Isla Mujeres Essential Tour, a 6-hour trip full of fun, relaxation and unforgettable moments....
Private Tour
Day Sails and Sunset tours on Schooner Surprise in Camden Maine
Sail onboard the only historic days sail schooner out of Camden Maine. Surprise was build in Rockport Massachusetts in 1918. We only carry 18 passengers in all cushions seats. Experienced crew will provide information on wild life... More
Private Tour

Day Sails and Sunset tours on Schooner Surprise in Camden Maine
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North America
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Superb12 reviews5
Sail onboard the only historic days sail schooner out of Camden Maine. Surprise was build in Rockpor....
Private Tour
Sailing Trip to Dia Island - All Inclusive
Our qualified team brings years of experience and a deep passion for the art of sailing. We take immense joy in every moment spent on the open sea, and it is our pleasure to extend that feeling to our valued customers. Relaxation ... More
Private Tour

Sailing Trip to Dia Island - All Inclusive
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North America
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Superb12 reviews5
Our qualified team brings years of experience and a deep passion for the art of sailing. We take imm....
Private Tour