Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 755 Sailing Trips activities in North America. Sort by Popularity. - Page 8Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pals on ou... More
Likely to Sell Out Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise
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North America
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Superb36 reviews5
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get so....
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
Likely to Sell Out New York City Sunset Sail to the Statue of Liberty
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North America
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Superb68 reviews4.8
Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of B....
Sightseeing Day Sail around Boston Harbor
Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail past the seaport district, Castle... More
Likely to Sell Out Sightseeing Day Sail around Boston Harbor
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North America
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Superb542 reviews4.8
Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner....
Isla Mujeres, Cancún Private Sunset Trip
Our tours are suited to your needs, as we want you to enjoy yourself, to simply let go, to watch the sunset and experience the moment. We are here to bring you the the quality service you so rightly deserve. Our adored crew ensure... More
Private Tour
Likely to Sell Out Isla Mujeres, Cancún Private Sunset Trip
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North America
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Superb81 reviews5
Our tours are suited to your needs, as we want you to enjoy yourself, to simply let go, to watch the....
Private Tour
Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor since 2012, our sailing yachts are the highest quality and operated ... More
Private Tour
Likely to Sell Out Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique
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North America
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Superb33 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
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
Likely to Sell Out 1.5-Hour San Francisco Bay Sailing Tour
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North America
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Superb398 reviews4.8
For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a....
Private Tour
Daytime Sailing Along San Diego's Skyline
Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor Sunroad Marina on Harbor Island on San Diego Bay, we often s... More
Private Tour
Likely to Sell Out Daytime Sailing Along San Diego's Skyline
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North America
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Superb146 reviews4.9
Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....
Private Tour
Sunset Cocktail Cruise on our Sailing Catamaran
Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohala Coast aboard our legendary sailing catamaran Seasmoke. This cruise includes unlimited soft drinks, tropical juices, beers, wines... More
Private Tour
Likely to Sell Out Sunset Cocktail Cruise on our Sailing Catamaran
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North America
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Superb62 reviews4.8
Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....
Private Tour
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise lets you see whales (December through March), fish, even green s... More
Private Tour
Likely to Sell Out Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
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North America
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Superb37 reviews4.6
Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....
Private Tour
Private Oahu Sunset Charter with Tasting and Drinks
This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people while enjoying the West Oahu Sunset on this 2.5-hour experience. There’s more than enoug... More
Private Tour
Likely to Sell Out Private Oahu Sunset Charter with Tasting and Drinks
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North America
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Superb50 reviews5
This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world....
Private Tour
Private Sailboat tour in Cabo San Lucas with Papillon Yachts
Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care of you to make this an unforgettable experience. Our all-inclusive and all-private tour will make sure you have everything you need... More
Private Tour
Likely to Sell Out Private Sailboat tour in Cabo San Lucas with Papillon Yachts
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North America
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Superb199 reviews5
Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care o....
Private Tour
Fort Lauderdale Sailing Charter
Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called the “Venice of America.” This scenic waterway offers a beautiful blend of natural mangroves, luxurious waterfront homes, and ... More
Private Tour
Likely to Sell Out Fort Lauderdale Sailing Charter
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North America
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Superb391 reviews5
Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called....
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
Likely to Sell Out Classic Key West Schooner Sunset Sail with Full Open Bar
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North America
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Superb230 reviews4.9
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....
Private Tour
Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams
This is a luxury Sailboat Excursion for up to 6 guests. Our 47 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 fu... More
Private Tour
Likely to Sell Out Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams
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North America
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Superb230 reviews4.9
This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow....
Private Tour
Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms
Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the sky transform into a palette of golden hues as the sun dips be... More
Private Tour
Likely to Sell Out Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms
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North America
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Superb51 reviews4.9
Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. Th....
Private Tour
Lāna'i Coast Snorkel and Sail
Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as we explore and snorkel the incredible coastline of Maui. Departing daily from 9:30 am - 2:30 pm. We'll check the conditions for t... More
Private Tour
Likely to Sell Out Lāna'i Coast Snorkel and Sail
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North America
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Superb30 reviews5
Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as....
Private Tour
Cabo San Lucas 34ft Private Yacht with Drinks Included
Set sail from Cabo San Lucas Marina on a private 34ft Formula yacht for an unforgettable 2-hour coastal cruise. As you glide past iconic landmarks like El Arco and Lover’s Beach, the professional captain and crew ensure a smooth... More
Private Tour
Likely to Sell Out Cabo San Lucas 34ft Private Yacht with Drinks Included
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North America
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Superb30 reviews5
Set sail from Cabo San Lucas Marina on a private 34ft Formula yacht for an unforgettable 2-hour coas....
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
Likely to Sell Out Snorkel Sail Adventure off Ka'anapali Beach, Maui
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North America
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Superb37 reviews4.9
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....
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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Superb10 reviews5
Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....
Private Tour
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
Private Tour
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....
Private Tour