Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 715 Sailing Trips activities in North America. Sort by Popularity. - Page 21Private Charleston Harbor Catamaran Sail
Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing catamaran. Our modern layout provides a panoramic view with large sliding glass doors between the saloon and the rear deck space, with... More
Private Tour
Private Charleston Harbor Catamaran Sail
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North America
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Superb29 reviews5
Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing cata....
Private Tour
Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelos
Embark on an unforgettable sailing adventure to the Puerto Morelos Reef, part of the Mesoamerican Barrier Reef System, the world’s second-largest coral reef. Departing daily at 9:00 a.m. and 2:00 p.m., your journey begins with a... More
Private Tour
Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelo....
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North America
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Very Good12 reviews3.8
Embark on an unforgettable sailing adventure to the Puerto Morelos Reef, part of the Mesoamerican Ba....
Private Tour
Guided Seattle Sailing Adventure from Bainbridge Island
Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning waterfront homes, and maybe even spot whales. Or we could see a nuclear submarine, inbound container ships, or century-old schooners... More
Private Tour
Guided Seattle Sailing Adventure from Bainbridge Island
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North America
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Superb85 reviews5
Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning wa....
Private Tour
Key West Dolphin Watch and Sunset Sail on Catamaran
Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of wind. This tour is perfect for all ages and offers a wide-open, unobs... More
Private Tour
Key West Dolphin Watch and Sunset Sail on Catamaran
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North America
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Superb43 reviews4.7
Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the ligh....
Private Tour
Deluxe private Sunset & Day Sail
Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic landmarks, and into the heart of coastal paradise. Feel the wind in your... More
Private Tour
Deluxe private Sunset & Day Sail
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North America
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Superb3 reviews5
Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling ....
Private Tour
Private Sailing Excursions, Nice Spacious Sailboats
Bacalar's lagoon is explored by sailboat with up to six guests, giving families and friends space to tailor the trip. Sail to cenotes, Bird Island, and Pirate Channel, use snorkeling equipment to explore underwater rock formations... More
Private Tour
Private Sailing Excursions, Nice Spacious Sailboats
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North America
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Superb41 reviews4.9
Bacalar's lagoon is explored by sailboat with up to six guests, giving families and friends space to....
Private Tour
Party On Sailing Cruise to Isla Mujeres from Cancun
Come join the party in our adults-only catamaran from Cancun to Isla Mujeres. Start the day with our national drinks onboard the catamaran. You will snorkel at one of the best reefs and see beautiful tropical fish, then eat lunch ... More
Private Tour
Party On Sailing Cruise to Isla Mujeres from Cancun
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North America
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Very Good19 reviews3.9
Come join the party in our adults-only catamaran from Cancun to Isla Mujeres. Start the day with our....
Private Tour
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)
(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot ca... More
Private Tour
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)
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North America
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Superb2 reviews5
(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....
Private Tour
Wrightsville Beach Day Sail Private Catamaran Charter
On this 4hr private charter, you will work with your captain to plan your perfect itinerary of islands and local spots. Upon anchoring, the crew will dinghy you around wherever you'd like to go! The boat is fully equipped with ai... More
Private Tour
Wrightsville Beach Day Sail Private Catamaran Charter
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North America
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Superb1 review5
On this 4hr private charter, you will work with your captain to plan your perfect itinerary of islan....
Private Tour
Private 90-Minute Harbor Sailing Charter in Key West
Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida Keys and view the city from the water in peace and tranquility. You may even get to see some fri... More
Private Tour
Private 90-Minute Harbor Sailing Charter in Key West
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North America
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Superb20 reviews4.9
Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-mi....
Private Tour
2-Hour Private Hilton Head Afternoon Dolphin Watching Sail
This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the North side of the island. During the day, this is generally filled with exciting winds for gre... More
Private Tour
2-Hour Private Hilton Head Afternoon Dolphin Watching Sail
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North America
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Superb125 reviews5
This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind....
Private Tour
Okanagan Lake Sailing Tour from Penticton & Naramata BC
Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht into the sunny waters of Okanagan Lake. We provide hands on instruction and lots of opportunities to learn or just relax. And it is ... More
Private Tour
Okanagan Lake Sailing Tour from Penticton & Naramata BC
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North America
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Superb52 reviews5
Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht int....
Private Tour
Baltimore Inner Harbor Sail on the Unforgettable
Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling city from the water. Explore the Inner Harbor and the joy of sailing on t... More
Private Tour
Likely to Sell Out Baltimore Inner Harbor Sail on the Unforgettable
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North America
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Superb25 reviews4.8
Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authe....
Private Tour
Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound
Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these waters back in 1792. From Seattle’s Shilshole Bay Marina we sail west across Puget Sound toward the magnificent Olympic Mountains. A... More
Private Tour
Likely to Sell Out Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound
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North America
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Superb36 reviews5
Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these wate....
Private Tour
Likely to Sell Out
Isla Mujeres Catamaran Sailing Experience with Lunch & Open Bar
Set off on a sun-and-fun-packed day trip to charming Isla Mujeres, a must-see attraction just off the Cancun coast. Cruise on a modern catamaran while sipping a drink or two from the open bar on your way to and from the scenic isl... More
Free Cancellation
Private Tour
(Saving 12% )
Likely to Sell Out Isla Mujeres Catamaran Sailing Experience with Lunch & Open Bar
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North America
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Very Good17 reviews3.6
Set off on a sun-and-fun-packed day trip to charming Isla Mujeres, a must-see attraction just off th....
Free Cancellation
Private Tour
(Saving 12% )
Likely to Sell Out
Key West Private Charter: Sandbar and Snorkeling
This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a formal, guided eco-tour, this trip offers a more laid-back vibe, allowing you t... More
Free Cancellation
Private Tour
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Likely to Sell Out Key West Private Charter: Sandbar and Snorkeling
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North America
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Superb20 reviews5
This private charter is designed for a relaxed, flexible day on the water, perfect for groups who wa....
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out
Deluxe Catamaran Tour to Isla Mujeres, Drinks, Snorkeling, Buffet
Get ready to venture into a fantastic experience aboard our catamaran to Isla Mujeres. You will board the catamaran and we will begin our tour together with our guides and entertainers so that you have a pleasant time. You can as... More
Free Cancellation
Private Tour
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Likely to Sell Out Deluxe Catamaran Tour to Isla Mujeres, Drinks, Snorkeling, Buffet
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North America
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Very Good28 reviews3.8
Get ready to venture into a fantastic experience aboard our catamaran to Isla Mujeres. You will boa....
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out
BYOB Friday Night Fireworks Cruise
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights and be in awe with this unobstructed view of fireworks from the water! With plenty of... More
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out BYOB Friday Night Fireworks Cruise
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North America
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Exellent6 reviews4.3
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out
Los Cabos Seasonal Whale Watch and Snorkel Tour
Available December 15th to April 15th. Enjoy an incredible adventure, departing from the beautiful Marina in Cabo San Lucas the boat as sails towards the Santa Maria or Chileno Bay, will ride along the Sea of Cortes, and you will ... More
Free Cancellation
Private Tour
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Likely to Sell Out Los Cabos Seasonal Whale Watch and Snorkel Tour
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North America
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Superb21 reviews4.7
Available December 15th to April 15th. Enjoy an incredible adventure, departing from the beautiful M....
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out
Hidden Beach - Marietas Islands
Spend the day exploring and enjoying the marine life of the Marietas Islands on this 5-hour excursion, departing from Puerto Vallarta. Even those without experience can feel comfortable participating in guided snorkeling excursion... More
Free Cancellation
Private Tour
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Likely to Sell Out Hidden Beach - Marietas Islands
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North America
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Exellent46 reviews4.3
Spend the day exploring and enjoying the marine life of the Marietas Islands on this 5-hour excursio....
Free Cancellation
Private Tour
(Saving inf% )