Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 721 Sailing Trips activities in North America. Sort by Popularity. - Page 8Best of Halifax Harbour Boat Tour
This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside our Captain and Deckhand throughout the relaxed harbour tour as they share Halifax's history and present day facts!... More

Best of Halifax Harbour Boat Tour
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North America
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Superb77 reviews4.9
This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside ....
Private Family Catamaran From Isla Mujeres
Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all day when you can do it in less time? Affordable Private Catamaran, avoid crowded vessels Half-day fun catamaran, with a guided sn... More
Private Tour

Private Family Catamaran From Isla Mujeres
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North America
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Superb1 review5
Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all....
Private Tour
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu
Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from December-March, of course, the annual humpback whales!... More
Private Tour

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu
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North America
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Superb17 reviews4.7
Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē....
Private Tour
2hr. SUNSET Sailing Experience on San Francisco Bay
This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sailing Experience is "interactive" which means we want you to get the full experience of sailing so you'll have an opportunity to tak... More
Private Tour

2hr. SUNSET Sailing Experience on San Francisco Bay
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North America
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Superb21 reviews5
This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sail....
Private Tour
Sunset Catamaran Sail in Cocoa Beach
Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the beauty of Florida... More
Private Tour

Sunset Catamaran Sail in Cocoa Beach
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North America
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Superb165 reviews4.9
Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning eveni....
Private Tour
Premium Isla Mujeres Tour by Private Catamaran
We specialize in making this all-day trip unique, a unique and beautiful experience for all our guests. This trip can always be customized as desired, as we offer 2 options to our customers. Our trained team is always there to pro... More
Private Tour

Premium Isla Mujeres Tour by Private Catamaran
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North America
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Superb278 reviews5
We specialize in making this all-day trip unique, a unique and beautiful experience for all our gues....
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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Superb423 reviews4.9
Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....
Private Tour
4-Hour St. Pete Pier to Egmont Key Experience by Ferry
From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stunning Sunshine Skyway bridge and perhaps see a dolphin or two! This is the only charter offering service from downtown St. Petersb... More
Private Tour

4-Hour St. Pete Pier to Egmont Key Experience by Ferry
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North America
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Superb302 reviews4.7
From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stu....
Private Tour
Windjammer Classic Day Sail from Camden, Maine
See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations on a modern windjammer. With wide ... More
Private Tour

Windjammer Classic Day Sail from Camden, Maine
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North America
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Superb408 reviews4.8
See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....
Private Tour
2hr. INTERACTIVE Sailing Experience on San Francisco Bay
This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More
Private Tour

2hr. INTERACTIVE Sailing Experience on San Francisco Bay
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North America
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Superb79 reviews5
This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....
Private Tour
Diamond Head Sunset Sail
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from the... More
Private Tour

Diamond Head Sunset Sail
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North America
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Superb15 reviews4.7
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....
Private Tour
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather permitting) while taking in the sun and spectacular views. Our beautifully, well appointed ... More
Private Tour

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
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North America
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Superb153 reviews4.9
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....
Private Tour
Private Sailing Charter with Captain, BYOB
Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's scenic Harbor. The golden hour of sunset is our prime booking time, offering... More
Private Tour

Private Sailing Charter with Captain, BYOB
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North America
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Superb62 reviews5
Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6....
Private Tour
Boat ride to the Arch and Snorkel
Check these must-do Cabo activities off your list and spend a proper day in the sun, relaxing on a smooth ride through the Sea of Cortez Our guide and captain who are biologists will share interesting and professional infor... More
Private Tour

Boat ride to the Arch and Snorkel
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North America
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Superb109 reviews4.9
Check these must-do Cabo activities off your list and spend a proper day in the sun, relaxing on a s....
Private Tour
2-Hour Private Sailboat Charter in the San Francisco Bay
Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Just kick back and celebrate your special event under the romance of sail. Private sailboat charters are a great way to celebrate you... More
Private Tour

2-Hour Private Sailboat Charter in the San Francisco Bay
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North America
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Superb20 reviews4.9
Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Jus....
Private Tour
Private Catamaran Charter in Waikiki (1-6 Guests)
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on the front of the boat, as well as 2 small nets on the back of the boat. Not only does Hawa... More
Private Tour

Private Catamaran Charter in Waikiki (1-6 Guests)
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North America
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Superb21 reviews5
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....
Private Tour
Classic Key West Schooner Sunset Sail with Full Open Bar
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Ke... More
Private Tour

Classic Key West Schooner Sunset Sail with Full Open Bar
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North America
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Superb190 reviews4.9
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....
Private Tour
1.5-Hour San Francisco Bay Sailing Tour
For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with beer and wine. This double-masted, teak-decked, bronze-fitted beauty hold... More
Private Tour

1.5-Hour San Francisco Bay Sailing Tour
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North America
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Superb390 reviews4.8
For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a....
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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Superb183 reviews5
After a successful first season I am happy to be here for back to back seasons. Sail in style on the....
Private Tour
9am 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
Private Tour

9am Turtle Canyon Snorkel Adventure
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North America
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Superb265 reviews4.9
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
Private Tour