Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 755 Sailing Trips activities in North America. Sort by Popularity. - Page 10Private Yacht Charter in Cabo San Lucas – Cruise to The Arch
Enjoy a private yachting experience in Cabo San Lucas without committing to a full-day tour. Perfect for couples, families, or small groups, this 2-hour cruise offers front-row views of El Arco, Lover’s Beach, and local sea lion... More
Private Tour
Likely to Sell Out Private Yacht Charter in Cabo San Lucas – Cruise to The Arch
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North America
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Superb1 review5
Enjoy a private yachting experience in Cabo San Lucas without committing to a full-day tour. Perfect....
Private Tour
Private Guided Sunset and Eco Tour up to 6 Passengers
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a cooler with bottled water a... More
Private Tour
Likely to Sell Out Private Guided Sunset and Eco Tour up to 6 Passengers
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North America
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Superb75 reviews5
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....
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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Superb18 reviews5
We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and mo....
Private Tour
Suncoast Sailing's Day Sailing Experience!
Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. Just wind in the sails, salt in the air, and the kind of quiet glide across t... More
Private Tour
Likely to Sell Out Suncoast Sailing's Day Sailing Experience!
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North America
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Superb112 reviews4.9
Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to fe....
Private Tour
Luxury Snorkel Adventure in Cabo
Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located at Santa Maria Bay or Chileno Bay, at either one of this beach areas is where boat captain will make a stop for snorkeling at one ... More
Private Tour
Likely to Sell Out Luxury Snorkel Adventure in Cabo
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North America
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Superb55 reviews4.8
Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located ....
Private Tour
Portland 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
Private Tour
Likely to Sell Out Portland Tall Ship Cruise on Casco Bay
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North America
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Exellent235 reviews4.5
What better way to see the delights of Portland than from the sea in one of the famous schooner tall....
Private Tour
Sailing Charters in Wilmington
After a successful first three seasons I am happy to be here for a fourth season!!! Sail in style on the historic Wilmington river walk. Enjoy a personalized Charter experience with up to six guests. Very few sailboats are up for ... More
Private Tour
Likely to Sell Out Sailing Charters in Wilmington
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North America
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Superb187 reviews5
After a successful first three seasons I am happy to be here for a fourth season!!! Sail in style on....
Private Tour
Catamaran Sailing Cruise in Monterey
Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind to make for a peaceful and exciting cruise on the bay. On the way out of t... More
Private Tour
Likely to Sell Out Catamaran Sailing Cruise in Monterey
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North America
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Superb35 reviews4.8
Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage af....
Private Tour
Best of Halifax Harbour Boat Tour
This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside our Captain and Deckhand throughout the relaxed harbour tour as they share Halifax's history and present day facts!... More
Private Tour
Likely to Sell Out Best of Halifax Harbour Boat Tour
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North America
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Superb77 reviews4.9
This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside ....
Private Tour
Chacahua Afternoon Journey
As a team we try to create journeys that are worth investing your time and confidence. We try to do our best to get out of the same schedules that our fellow colleagues offer this tour is whole afternoon experience that show us al... More
Private Tour
Likely to Sell Out Chacahua Afternoon Journey
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North America
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Superb47 reviews4.8
As a team we try to create journeys that are worth investing your time and confidence. We try to do ....
Private Tour
Molokini Snorkel and Performance Sail: Mā’alaea Harbor
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More
Private Tour
Likely to Sell Out Molokini Snorkel and Performance Sail: Mā’alaea Harbor
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North America
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Superb217 reviews4.8
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
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
Likely to Sell Out 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
Halifax Sunset Cruise Ft. a Live Musician
Experience golden hour, that magical time of night when the sun makes its way below the horizon, on the Halifax Sunset Cruise aboard our signature ship, the Tall Ship Silva. Purchase wine, beer, cocktails, and other beverages from... More
Private Tour
Likely to Sell Out Halifax Sunset Cruise Ft. a Live Musician
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North America
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Superb47 reviews4.7
Experience golden hour, that magical time of night when the sun makes its way below the horizon, on ....
Private Tour
2-Hour Private Sailing Experience in San Diego Bay
Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing to obtain in today's world. With all the stress life brings we are happy to provide a peacefu... More
Private Tour
Likely to Sell Out 2-Hour Private Sailing Experience in San Diego Bay
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North America
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Superb171 reviews5
Our unique sail displays a peace sign because that is exactly what we share with our customers, peac....
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
Likely to Sell Out Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak
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North America
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Superb101 reviews4.9
Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authent....
Private Tour
Sailing Tour through the Lagoon of the 7 Colors
Sail with people who share your passion for adventure! You will explore fascinating places along the lagoon of the 7 colors. Our small groups guarantee you excellent attention and service from our crew. Disconnect from the world ... More
Private Tour
Likely to Sell Out Sailing Tour through the Lagoon of the 7 Colors
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North America
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Superb1,180 reviews4.9
Sail with people who share your passion for adventure! You will explore fascinating places along the....
Private Tour
Boat Fishing Tour, Puerto Morelos CIPREA, 25'
We are a team with 20 years of experience in sport fishing tour only. Newbies and experts are welcome. Come and enjoy the beauties of the Caribbean Sea, the setting where we fish We have the best boats in Puerto Morelos. Come an... More
Private Tour
Likely to Sell Out Boat Fishing Tour, Puerto Morelos CIPREA, 25'
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North America
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Superb2 reviews5
We are a team with 20 years of experience in sport fishing tour only. Newbies and experts are welco....
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
Likely to Sell Out Private sailing tour of Bacalar Lagoon
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North America
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Superb435 reviews5
Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper ....
Private Tour
Windjammer Classic Day Sail from Camden, Maine
See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations on a modern windjammer. With wide ... More
Private Tour
Likely to Sell Out Windjammer Classic Day Sail from Camden, Maine
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North America
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Superb407 reviews4.8
See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....
Private Tour
Los Cabos Sunset Sailing Adventure
Experience a breathtaking sunset sail on the Cabo San Lucas Bay aboard a luxury catamaran, complete with delicious appetizers and an international open bar. After being picked up from your hotel, embark from the Cabo San Lucas Mar... More
Private Tour
Likely to Sell Out Los Cabos Sunset Sailing Adventure
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North America
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Superb1 review5
Experience a breathtaking sunset sail on the Cabo San Lucas Bay aboard a luxury catamaran, complete ....
Private Tour