Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 725 Sailing Trips activities in North America. Sort by Popularity. - Page 14San Diego Private Morning Sail up to 12 guests
This private morning sail is a great way to start the day. Mornings are best to go see San Diego's wildlife because there is little wind and few waves, allowing us to easily cross over to Point Loma. The bay will most likely have ... More
Private Tour

San Diego Private Morning Sail up to 12 guests
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North America
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Superb33 reviews5
This private morning sail is a great way to start the day. Mornings are best to go see San Diego's 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

Private Catamaran Sunset Sail in Waikiki
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North America
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Superb8 reviews5
Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....
Private Tour
Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise
Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay and National Seashore. Or explore the Condor: walk around, do the Titanic po... More
Private Tour

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise
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North America
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Superb33 reviews4.9
Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chil....
Private Tour
JFarwell Adventure Yacht Sailing in the Halifax Harbour
Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the water, and offers a great introduction to sailing. Guests are encouraged to be as hands on with the sailing process as they would... More
Private Tour

JFarwell Adventure Yacht Sailing in the Halifax Harbour
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North America
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Superb147 reviews5
Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the....
Private Tour
South Shore Open Sail from Kewalo Harbor Including Drinks
Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! We are a 49-passenger beautiful yellow and red retired Waikiki Beach catamaran now operating from Kewalo... More
Private Tour

South Shore Open Sail from Kewalo Harbor Including Drinks
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North America
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Superb17 reviews5
Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....
Private Tour
Friday Night Firework Cruise in Waikiki
After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, truly making this the ultimate party experience. Enjoy the Premium drinks of your choice ... More
Private Tour

Friday Night Firework Cruise in Waikiki
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North America
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Superb23 reviews4.7
After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....
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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Superb37 reviews4.8
Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. Th....
Private Tour
Romantic Lobster Dinner Cruise at Sunset
Cruise across the scenic Nichupte Lagoon on an elegant Spanish Galeon, treating your better half to an amazing romantic experience and an exquisite 3-course dinner. Following you check-in, get aboard the spectacular ship under t... More
Private Tour

Romantic Lobster Dinner Cruise at Sunset
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North America
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Superb10 reviews4.6
Cruise across the scenic Nichupte Lagoon on an elegant Spanish Galeon, treating your better half to ....
Private Tour
Sunset sail Aboard Manakai Catamaran
Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a smaller guest capacity and open-deck layout, it offers an intimate, lai... More
Private Tour

Sunset sail Aboard Manakai Catamaran
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North America
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Superb5 reviews5
Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Wood....
Private Tour
Private Sunset Sail BYOB Dolphin/History Tours 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 for over 12 years, our sailing yachts are the highest quality and op... More
Private Tour

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique
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North America
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Superb41 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour
Sailing Tour through the Laguna de los Siete Colores
Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, being your best option to know this magical place without damaging the ecosystem. Guided by a team of professionals, with whom you ... More
Private Tour

Sailing Tour through the Laguna de los Siete Colores
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North America
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Superb1,437 reviews5
Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, b....
Private Tour
Private Kelowna Sailing Cruise on Okanagan Lake
Sailing is a quiet, peaceful experience, as the boat is powered by nothing but the wind. You are welcome to sit back and relax, enjoy the sights, or take a turn at the helm, with instruction from your skipper! I will never forg... More
Private Tour

Private Kelowna Sailing Cruise on Okanagan Lake
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North America
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Superb42 reviews5
Sailing is a quiet, peaceful experience, as the boat is powered by nothing but the wind. You are w....
Private Tour
2 Hour Sunset Sailing Tour in Wrightsville Beach
Our experienced captains will sail you to the most beautiful local spots to watch the sunset on the water. Spot dolphins, seabirds, and other wildlife as you pass by islands and marshlands.... More
Private Tour

2 Hour Sunset Sailing Tour in Wrightsville Beach
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North America
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Superb3 reviews5
Our experienced captains will sail you to the most beautiful local spots to watch the sunset on the ....
Private Tour
Schooner Eastwind Sunset Sail to see the Maine Coastline
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 Sunset Sail to see the Maine Coastline
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North America
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Superb61 reviews4.7
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....
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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Superb84 reviews4.9
Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authent....
Private Tour
Your Private Miami Yacht Tour with Music and Champagne
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

Your Private Miami Yacht Tour with Music and Champagne
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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
4-Hour Sailing Adventure on The Strait of Juan de Fuca
Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbacks, Orcas, Sea lions, Seals, Eagles and water birds there is always something to see while you are learning the skills to sail one... More
Private Tour

4-Hour Sailing Adventure on The Strait of Juan de Fuca
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North America
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Superb26 reviews4.7
Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbac....
Private Tour

6hrs of Sailing in Bacalar Lagoon: discover Cenotes, Islands and Stromatolites.
Ideal for adventurers and sailing lovers! Explore the most emblematic points of the lagoon, or modify the route to discover areas far from tourism. 6 hours of deep exploration and adventure where you can get to know: The Pirate Ch... More
Free Cancellation
Private Tour
(Saving 10% )

6hrs of Sailing in Bacalar Lagoon: discover Cenotes, Islands and ....
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North America
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Superb18 reviews5
Ideal for adventurers and sailing lovers! Explore the most emblematic points of the lagoon, or modif....
Free Cancellation
Private Tour
(Saving 10% )
Jolly Roger Pirate Show Cancun with Transportation
Become a pirate for a night by teaming up with Jolly Roger's cheerful crew! Embark on a fun-packed sunset cruise on the gorgeous Spanish Galleon for the ideal evening out with the whole family. The buccaneers start greeting you a... More
Private Tour

Jolly Roger Pirate Show Cancun with Transportation
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North America
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Superb14 reviews5
Become a pirate for a night by teaming up with Jolly Roger's cheerful crew! Embark on a fun-packed s....
Private Tour
Sail Away: Explore Maine's Coastal Beauty on a 2-Hour Excursion
Step aboard for an unforgettable journey along Maine's stunning coastline! Join us for a two-hour sail and create memories to cherish forever. Experience the beauty of Maine as you glide through the waters of the Saco River and Sa... More
Private Tour

Sail Away: Explore Maine's Coastal Beauty on a 2-Hour Excursion
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North America
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Superb42 reviews4.9
Step aboard for an unforgettable journey along Maine's stunning coastline! Join us for a two-hour sa....
Private Tour