Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 673 Sailing Trips activities in North America. Sort by Popularity. - Page 15Deluxe Day Sail in San Diego
Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego Bay offer a perfect blend of adventure and relaxation. With our passionate and kno... More
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Deluxe Day Sail in San Diego
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North America
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Superb47 reviews5
Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our person....
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Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vess... More

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
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North America
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Superb20 reviews4.8
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....
Sunset Luxury Sail on Tampa Bay
Set sail aboard Hawkeye, a brand-new 47-foot luxury sailboat made locally by Island Packet Yachts. Cruise along Downtown St. Petersburg’s scenic waterfront and watch the city glisten in the setting sun. This is a luxury, two-ho... More

Sunset Luxury Sail on Tampa Bay
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North America
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Superb8 reviews5
Set sail aboard Hawkeye, a brand-new 47-foot luxury sailboat made locally by Island Packet Yachts. C....
Los Angeles: 1 hour group yacht cruise -(1 ticket covers 1-6 ppl)
You may bring 1-6 people on this activity. One ticket covers you and your guests, Enjoy a 1 hr private group swim trip aboard our 42 ft Bertram-Trojan Motor Yacht. Consider booking multiple blocks for a longer trip.... More
Private Tour

Los Angeles: 1 hour group yacht cruise -(1 ticket covers 1-6 ppl)
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North America
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Superb1 review5
You may bring 1-6 people on this activity. One ticket covers you and your guests, Enjoy a 1 hr priva....
Private Tour
Sea to Sky Afternoon Sail
Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds with the breathtaking views of the Coastal and Tantalus mountain ranges. We will depart from the docks in Squamish (about 40 minut... More
Private Tour

Sea to Sky Afternoon Sail
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North America
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Superb198 reviews5
Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds w....
Private Tour
Escape from the Rock! Cruise around Alcatraz
Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and past Angel Island State Park before circling Alcatraz Island for an in-depth view of the prison. Take in the sights and sounds of ... More
Private Tour

Escape from the Rock! Cruise around Alcatraz
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North America
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Exellent154 reviews4.2
Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and ....
Private Tour
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
Private Tour

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak
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North America
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Superb30 reviews4.9
Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authent....
Private Tour
Polynesian Canoe Morning Sail
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More
Private Tour

Polynesian Canoe Morning Sail
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North America
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Superb16 reviews5
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Private Tour
Isla Mujeres Sailing Adventure from Riviera Maya
Enjoy an amazing sailing journey to Isla Mujeres on a 40ft Fountaine Pajot luxury vessel. Surrounded by all the scale of blue colors, you'll relax and chill, laying in the shade of the big cockpit or in a comfortable living r... More
Private Tour

Isla Mujeres Sailing Adventure from Riviera Maya
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North America
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Very Good12 reviews3.7
Enjoy an amazing sailing journey to Isla Mujeres on a 40ft Fountaine Pajot luxury vessel. Surroun....
Private Tour
FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry
Take advantage of the vicinity of the Bahamas Islands during your Florida visit to experience the world's best beaches. The ocean crossing is provided with our comfortable Express-Ferry featuring restrooms, comfortable seats, air ... More
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FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry
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North America
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Very Good9 reviews3.9
Take advantage of the vicinity of the Bahamas Islands during your Florida visit to experience the wo....
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Private Tour
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Boat & Yacht Tour Amazing Sandbar Adventure, Water Toys & Snorkel
Enjoy the day on the water with friends and family with Dolphin Water Sport. Our +650 reviews on Google with a score of 4.9 guarantee our quality. Come aboard our Boat and Yacht to enjoy an incredible Boat Trip in Miami. We'll cr... More
Private Tour

Boat & Yacht Tour Amazing Sandbar Adventure, Water Toys & Snorkel
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North America
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Very Good9 reviews3.9
Enjoy the day on the water with friends and family with Dolphin Water Sport. Our +650 reviews on Goo....
Private Tour
Private sailing tour of Bacalar Lagoon
Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper you. During the tour, you can enjoy a delicious fruit cocktail, water and beer. Our certified guides will make this tour an unfo... More
Private Tour

Private sailing tour of Bacalar Lagoon
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North America
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Superb275 reviews5
Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper ....
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

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms
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North America
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Superb2 reviews5
Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. Th....
Private Tour
Private Sailing between Mangroves
Within the activities of this tour, it will be bird watching, sailing in an ecological way without motor. We will swim in the places with the most crystalline water. we will eat exotic local seasonal fruit. With only your group,... More
Private Tour

Private Sailing between Mangroves
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North America
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Superb127 reviews5
Within the activities of this tour, it will be bird watching, sailing in an ecological way without m....
Private Tour
Pau Hana Sunset Cocktail Cruise
Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed catamaran. This cruise includes unlimited soft drinks, tropical juices, beers, wines, cocktails and a variety of appetizers.. Great f... More
Private Tour

Pau Hana Sunset Cocktail Cruise
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North America
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Superb48 reviews4.8
Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed cat....
Private Tour
Honolulu BYOB Fireworks Boat Cruise
Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring your favorite beverages and join us for Waikiki's weekly fireworks displ... More
Private Tour

Honolulu BYOB Fireworks Boat Cruise
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North America
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Exellent25 reviews4.5
Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....
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. We wi... More
Private Tour

Afternoon Half-Day Catmaran Sailing and Snorkel Adventure
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North America
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Exellent70 reviews4.5
Want to enjoy a sailing tour, where you can snorkel and visit Isla Mujeres in just half a day? This ....
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
Amazing Snorkeling Experience + Real Mexican Tacos
This is the classic snorkeling experience when you come to Cancun, it is a must tour in your Itinerary. When you do this experience you feel a connection with nature, it is like taking a little bit of Cancun with you back home. Se... More
Private Tour

Amazing Snorkeling Experience + Real Mexican Tacos
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North America
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Superb9 reviews4.8
This is the classic snorkeling experience when you come to Cancun, it is a must tour in your Itinera....
Private Tour
Puerto Vallarta Sunset Gourmet Experience
This experience blends fine dining, stunning scenery, and exceptional service in a way that few can match. The journey begins with a luxury catamaran cruise, offering panoramic views of Puerto Vallarta’s coastline at sunset. Unl... More
Private Tour

Puerto Vallarta Sunset Gourmet Experience
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North America
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Superb7 reviews4.7
This experience blends fine dining, stunning scenery, and exceptional service in a way that few can ....
Private Tour