Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 727 Sailing Trips activities in North America. Sort by Popularity. - Page 14Portland Tall Ship Cruise on Casco Bay
What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.... More
Portland Tall Ship Cruise on Casco Bay
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North America
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Superb234 reviews4.6
What better way to see the delights of Portland than from the sea in one of the famous schooner tall....
Two Hour Coastal Sailing Cruise
What makes this tour unique is the custom experience aboard our 43-foot, 27-foot wide trimaran—one of the largest and most stable sailing vessels in Savannah. Unlike crowded tour boats, our open-deck layout offers plenty of room... More
Two Hour Coastal Sailing Cruise
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North America
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Superb21 reviews5
What makes this tour unique is the custom experience aboard our 43-foot, 27-foot wide trimaran—one....
Seattle Sailing Harbor Tour
Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing tour is family-friendly and is an excellent way to see the Seattle skyline, the beauty of the Puget Sound, even mountain views! We ... More
Seattle Sailing Harbor Tour
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North America
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Superb473 reviews4.7
Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing t....
Skagway Trail and Sail
This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike Electric Bicycles where you will join us for a self-guided ride to some of Skagway's best sites! You will visit a waterfall, scenic... More
Likely to Sell Out Skagway Trail and Sail
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North America
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Superb5 reviews4.8
This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike E....
Isla Contoy Experience incl. Breakfast and Lunch
Your adventure kicks off at Marina Punta Norte, from where you'll sail towards Isla Mujeres while enjoying breakfast on board. You'll have an hour or so to explore the island or lounge on one of its powdery beaches. Hop back on th... More
Likely to Sell Out Isla Contoy Experience incl. Breakfast and Lunch
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North America
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Superb5 reviews4.8
Your adventure kicks off at Marina Punta Norte, from where you'll sail towards Isla Mujeres while en....
Deluxe Turtle Snorkeling Escapade at Waikiki
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More
Likely to Sell Out Deluxe Turtle Snorkeling Escapade at Waikiki
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North America
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Superb7 reviews4.9
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
JFarwell Sunset Wine and Cheese Yacht Sailing
Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to invite our guests to be involved in sailing - take the helm, hoist the sails, or sit back and enjoy the beautiful sights and wines ... More
Likely to Sell Out JFarwell Sunset Wine and Cheese Yacht Sailing
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North America
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Superb149 reviews4.9
Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to i....
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak
Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands... More
Likely to Sell Out Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak
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North America
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Superb90 reviews4.9
Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authent....
Cozumel Private Snorkeling and Charter Experience
We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On this tour, you'll have your own completely private charter visiting the famous 'El Cielo' and other amazing destinations to give you... More
Private Tour
Likely to Sell Out Cozumel Private Snorkeling and Charter Experience
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North America
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Superb24 reviews5
We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On th....
Private Tour
2.5 hr Sailboat Tour aboard Orion's Child
TripAdvisor Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel. Multiple daily sails that include a quarter day and sunset sail aboard a ... More
Private Tour
Likely to Sell Out 2.5 hr Sailboat Tour aboard Orion's Child
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North America
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Superb68 reviews5
TripAdvisor Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer t....
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. The t... More
Private Tour
Likely to Sell Out Afternoon Half-Day Catmaran Sailing and Snorkel Adventure
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North America
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Exellent71 reviews4.5
Want to enjoy a sailing tour, where you can snorkel and visit Isla Mujeres in just half a day? This ....
Private Tour
Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling
Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing cruise. Explore pristine beaches and beautiful sights while savoring fresh guacamole and a selection of delicious snacks. This pe... More
Private Tour
Likely to Sell Out Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling
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North America
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Superb69 reviews5
Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing ....
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
Likely to Sell Out Experience Oceanside Sailing with Whales and dolphins!
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North America
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Superb14 reviews5
We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and mo....
Private Tour
Nights of Lights Sailboat Tour St Augustine Sailing
What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours offer a simple ride, St Augustine Sailing provides an intimate, serene setting ... More
Private Tour
Likely to Sell Out Nights of Lights Sailboat Tour St Augustine Sailing
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North America
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Superb4 reviews5
What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experien....
Private Tour
Cancun Pirate Ship Adventure : Dinner & Show at Sea 2 for 1 Deal
Set sail EN an unforgettable adventure at DEcer with the Pirate Ship EN Cancun show, aboard a majestic Spanish galleon DE. Experience an exciting pirate experience filled DE games, contests and the fascinating stories of the Capta... More
Private Tour
Likely to Sell Out Cancun Pirate Ship Adventure : Dinner & Show at Sea 2 for 1 Deal
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North America
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Superb4 reviews5
Set sail EN an unforgettable adventure at DEcer with the Pirate Ship EN Cancun show, aboard a majest....
Private Tour
Sunset Sail Cruise in Key West
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail scho... More
Private Tour
Likely to Sell Out Sunset Sail Cruise in Key West
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North America
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Superb253 reviews4.9
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....
Private Tour
Whale-Watching Pirate Ship Cruise in Los Cabos
Go whale-watching in Cabo San Lucas aboard a real pirate ship called the Bucaneer Queen. Sail the Pacific Ocean and the Sea of Cortez in search of these amazing creatures. You will be accompanied by an experienced bilingual guide ... More
Private Tour
Likely to Sell Out Whale-Watching Pirate Ship Cruise in Los Cabos
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North America
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Superb103 reviews4.7
Go whale-watching in Cabo San Lucas aboard a real pirate ship called the Bucaneer Queen. Sail the Pa....
Private Tour
Your Private Miami Yacht Tour with Music and Fun
Leave the city's hustle behind and discover Miami from a fresh perspective. On this unforgettable journey, our luxurious yacht becomes your private oasis on the water. As we navigate the breathtaking waters of Biscayne Bay, you'll... More
Private Tour
Likely to Sell Out Your Private Miami Yacht Tour with Music and Fun
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North America
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Superb65 reviews4.6
Leave the city's hustle behind and discover Miami from a fresh perspective. On this unforgettable jo....
Private Tour
Private Catamaran Sunset Sail in Waikiki
Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large ... More
Private Tour
Likely to Sell Out Private Catamaran Sunset Sail in Waikiki
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North America
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Superb9 reviews5
Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....
Private Tour
Private Sunset Sailing Cruise in Puerto Vallarta
On this sunset sailing experience you will be able to apreciate a relaxing sunset while you take on stunning views of the Sierra Madre mountains and the prettiest areas of Down Town Puerto Vallarta. While on tour we provide 2 cour... More
Private Tour
Likely to Sell Out Private Sunset Sailing Cruise in Puerto Vallarta
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North America
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Superb25 reviews5
On this sunset sailing experience you will be able to apreciate a relaxing sunset while you take on ....
Private Tour