Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 671 Sailing Trips activities in North America. Sort by Popularity. - Page 14Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat
This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for f... More
Private Tour

Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat
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North America
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Superb28 reviews5
This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bo....
Private Tour
Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More
Private Tour

Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan
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North America
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Superb24 reviews5
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....
Private Tour
2-Hour Sunset Sailing With Wine In Stock Island
Sail with a smaller group of guests on our 65 foot schooner. Enjoy wines from around the world. Indulge in a variety of IPA, Import or domestic beers. Taste an assortment of appetizers. Enjoy a beautiful sunset while on the water.... More
Private Tour

2-Hour Sunset Sailing With Wine In Stock Island
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North America
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Superb76 reviews5
Sail with a smaller group of guests on our 65 foot schooner. Enjoy wines from around the world. Indu....
Private Tour
Snorkel Sail Adventure off Ka'anapali Beach, Maui
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buff... More
Private Tour

Snorkel Sail Adventure off Ka'anapali Beach, Maui
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North America
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Superb9 reviews4.9
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....
Private Tour
Waikiki Sail and Snorkel Adventure Best of Hawaii 2023
Immerse yourself in a vibrant underwater wonderland as you snorkel through coral reefs teeming with an array of tropical fish. The clear waters of Turtle Canyons reveal a kaleidoscope of colors, from dazzling schools of fish to vi... More
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Waikiki Sail and Snorkel Adventure Best of Hawaii 2023
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North America
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Very Good4 reviews4
Immerse yourself in a vibrant underwater wonderland as you snorkel through coral reefs teeming with ....
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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Superb62 reviews5
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....
Private Tour
Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon
Bacalar is the perfect place to live this experience. This wonderful region has the calmest waters in the Caribbean and has the most fascinating tropical landscapes. You will visit the most beautiful places in the lagoon where yo... More
Private Tour

Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon
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North America
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Superb68 reviews5
Bacalar is the perfect place to live this experience. This wonderful region has the calmest waters i....
Private Tour
Afternoon Sail On A Charming Vintage Yacht Beer &. Wine Included
Book an unforgettable tour with Captain Phil and sail in style aboard Liberty, a stunning replica of a 1904 gaff-rigged Friendship sloop. Her best features include highly-finished woodwork, bronze fixtures, and gaff rigging that s... More
Private Tour

Afternoon Sail On A Charming Vintage Yacht Beer &. Wine Included
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North America
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Superb66 reviews5
Book an unforgettable tour with Captain Phil and sail in style aboard Liberty, a stunning replica of....
Private Tour
JFarwell Best of Halifax Harbour Tour
This 45' sailing yacht is the perfect venue to learn about the history of Halifax. You are alongside our Captain and Deckhand throughout the sailing experience, and encouraged to ask questions about landmarks and things you see i... More
Private Tour

JFarwell Best of Halifax Harbour Tour
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North America
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Superb48 reviews5
This 45' sailing yacht is the perfect venue to learn about the history of Halifax. You are alongsid....
Private Tour
Day Sailing Adventure in the Florida Marine Sanctuary
Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Layâ€. Choose a 3-hour Day Sail or our popular Sunset Sail through the Florida Keys Marine Sanctuary in Marathon, Florida. Our sailbo... More
Private Tour

Day Sailing Adventure in the Florida Marine Sanctuary
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North America
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Superb11 reviews5
Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Layâ....
Private Tour
New York City Sunset Sail to the Statue of Liberty
Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic sailboat is 105-feet in length and has about 3600 square feet of sail ... More
Private Tour

New York City Sunset Sail to the Statue of Liberty
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North America
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Superb54 reviews4.9
Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of B....
Private Tour
Halifax Sunset Cruise
Experience golden hour, that magical time of night when the sun makes its way below the horizon, on the Halifax Sunset Cruise aboard our signature ship, the Tall Ship Silva. Purchase wine, beer, cocktails, and other beverages from... More
Private Tour

Halifax Sunset Cruise
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North America
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Superb2 reviews5
Experience golden hour, that magical time of night when the sun makes its way below the horizon, on ....
Private Tour
Experience Oceanside Sailing with Whales and dolphins!
We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and most comfortable sailboats in the Oceanside harbor. We cater to guests from many of the five star hotels in the area. We serve an up... More
Private Tour

Experience Oceanside Sailing with Whales and dolphins!
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North America
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Superb11 reviews5
We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and mo....
Private Tour
Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goa... More
Private Tour

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
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North America
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Superb71 reviews4.6
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....
Private Tour

Waikiki Fireworks Cocktail Cruise
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North America
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Exellent4 reviews4.3
Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a b....
Private Tour
Private Sailing Charter: Up to 24 Passengers
Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a spectacular private sail around the San Francisco Bay. While our boats are coast guard licensed for 34 passengers, we are limiting... More
Private Tour

Private Sailing Charter: Up to 24 Passengers
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North America
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Superb1 review5
Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a ....
Private Tour
Isla Mujeres by Private Catamaran
Discover Isla Mujeres, explore a world filled with vibrant colors, fascinating marine life, and crystal-clear waters that will make you feel like you're on another planet. Sail on an exclusive private catamaran, where you'll enjo... More
Private Tour

Isla Mujeres by Private Catamaran
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North America
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Superb1 review5
Discover Isla Mujeres, explore a world filled with vibrant colors, fascinating marine life, and crys....
Private Tour
Oahu 3pm Tradewind Sail from Honolulu
This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoon in the sun. We'll be keeping a sharp eye out for dolphins, whales and other sea life while getting as close as possible so you c... More
Private Tour

Oahu 3pm Tradewind Sail from Honolulu
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North America
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Superb229 reviews4.8
This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoo....
Private Tour
2 Hour Rosé Luxury Day Sail
This 2-hour daytime sail offers a smooth, spacious ride through the scenic Calibogue Sound with expert captains leading the way. Keep an eye out for dolphins, seabirds, and Lowcountry landmarks as you relax, unwind, and enjoy the ... More
Private Tour

2 Hour Rosé Luxury Day Sail
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North America
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Superb229 reviews4.8
This 2-hour daytime sail offers a smooth, spacious ride through the scenic Calibogue Sound with expe....
Private Tour

12pm Turtle Canyon Snorkel Adventure
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More
Free Cancellation
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12pm Turtle Canyon Snorkel Adventure
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North America
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Superb274 reviews4.8
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
Free Cancellation
Private Tour
(Saving 20% )