Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 714 Sailing Trips activities in North America. Sort by Popularity. - Page 19Private Sailing Tour through the Ten Thousands Islands
If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos where built in the early 80s and are known through out the sailing community as the fastest, driest, beachable catamaran on the ma... More
Private Sailing Tour through the Ten Thousands Islands
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North America
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Superb156 reviews4.9
If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos ....
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
Windjammer Classic Day Sail from Camden, Maine
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North America
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Superb467 reviews4.8
See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....
Private Tour
Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling
Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical waters alongside colorful sea life. The bilingual crew is happy to accommodate any special occasion or request. This unforgettable ex... More
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Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling
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North America
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Superb193 reviews5
Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical water....
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Miami Private Yacht Celebration Cruise with Captain
Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate like never before. This VIP experience is designed for fun, style, and unforgettable memories with your group. Adventure Highlig... More
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Miami Private Yacht Celebration Cruise with Captain
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North America
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Superb65 reviews4.6
Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate....
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Cozumel Private Snorkeling and Charter Experience
We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On this tour, you'll have your own completely private charter visiting the famous 'El Cielo' and other amazing destinations to give you... More
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Cozumel Private Snorkeling and Charter Experience
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North America
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Superb30 reviews4.9
We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On th....
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Tulum: Snorkeling and Private Sailing Tour
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North America
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Superb172 reviews4.9
We will enjoy a wonderful catamaran tour, powered only by the wind, we will be able to enjoy a spect....
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2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea, this intimate evening cruise offers stunning views of the coast... More
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2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
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North America
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Superb20 reviews4.9
Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experien....
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Private Customizable Sailing Tour in Cancun
Enjoy a private sailing tour for just you and your party aboard a private sailboat which offers the opportunity to visit wonderful places that can only be known by the sea. From a relaxing private sailing tour in the bay of Can... More
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Private Customizable Sailing Tour in Cancun
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North America
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Superb123 reviews4.7
Enjoy a private sailing tour for just you and your party aboard a private sailboat which offers th....
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Private Sailboat + Captain for a Day Experience
RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY TRIPADVISOR TRAVELER'S CHOICE AWARDS 2022!!! Everyone´s favorite! Enjoy an easy ride around the most relevant landmarks in the lagoon on board of a beautif... More
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Private Sailboat + Captain for a Day Experience
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North America
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Superb612 reviews5
RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY TRIPADVISOR TRAVELER'S CHOI....
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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
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Luxury Snorkel Adventure in Cabo
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North America
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Superb60 reviews4.9
Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located ....
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Likely to Sell Out
Polynesian Canoe Sunset Sail
Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and bec... More
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Likely to Sell Out Polynesian Canoe Sunset Sail
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North America
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Superb129 reviews4.9
Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) off....
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Likely to Sell Out
Deluxe Private Boats - 40 ft Catamaran
We are a company that understands privacy, attention to detail, and quality in everything we get our hands-on. We want you to feel relaxed and at home. We understand you are here to be pampered and have the nicest drinks and lunc... More
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Likely to Sell Out Deluxe Private Boats - 40 ft Catamaran
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North America
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Superb132 reviews5
We are a company that understands privacy, attention to detail, and quality in everything we get our....
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Likely to Sell Out
Visit Private Beaches around Puerto Vallarta in a Private Yacht
Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours don’t go. Also enjoy the explanation from our captain on the art of sailing. This is not a boat trip, this is an experience to enj... More
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Likely to Sell Out Visit Private Beaches around Puerto Vallarta in a Private Yacht
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North America
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Superb135 reviews5
Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours do....
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Likely to Sell Out
Luxury Catamaran tour to isla mujeres with transportation from Tulum
Excellent service on board Professional crew members Safety measures in all our activities Sanitary prevention protocols for all our guests and staff Once in a lifetime experience Delicious buffet lunch and drinks Beach club (beac... More
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Likely to Sell Out Luxury Catamaran tour to isla mujeres with transportation from Tu....
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North America
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Good66 reviews3.5
Excellent service on board Professional crew members Safety measures in all our activities Sanitary ....
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Private Tour
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Likely to Sell Out
JFarwell Moonlight Yacht Cruise from Halifax Waterfront
Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the Captain and passengers for a social sail - or laying on the bow relaxing under the stars, this moonlight sail is ultimate freedom! ... More
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Likely to Sell Out JFarwell Moonlight Yacht Cruise from Halifax Waterfront
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North America
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Superb52 reviews4.7
Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the C....
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Likely to Sell Out
The Finest Private Yacht Experience in Cabo
This 3hrs activity is the epitome of what the visitors have been coming to Cabo San Lucas for for 30+ years, it consists of some of the best things to do in Cabo such as whale watching and bathing on soothing crystal waters... More
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Likely to Sell Out The Finest Private Yacht Experience in Cabo
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North America
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Superb23 reviews4.6
This 3hrs activity is the epitome of what the visitors have been coming to Cabo San Lucas for for 30....
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Likely to Sell Out
2hr Shared Sailing Experience in Toronto
On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out for the ferry, reported to be the shortest commercial one in the world. Below the water is a walking tunnel connecting the two for t... More
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Likely to Sell Out 2hr Shared Sailing Experience in Toronto
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North America
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Superb27 reviews5
On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out fo....
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Likely to Sell Out
Key West: Sunset Sail + Reef Snorkel & Sandbar
Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? • Guided Snorkeling Your mate hops in the water with you and points out animals and shows yo... More
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Likely to Sell Out Key West: Sunset Sail + Reef Snorkel & Sandbar
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North America
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Superb56 reviews5
Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. Wh....
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Private Tour
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Likely to Sell Out
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
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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....
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Private Tour
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Likely to Sell Out
Snorkeling Adventure in Puerto Morelos with snack and round trip
You must live this experience once in your life, This activity is only for travelers that love to be in a unique place in the world. You will discover the 2nd biggest reef wall in the world, you will see a huge variety of fish of... More
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Likely to Sell Out Snorkeling Adventure in Puerto Morelos with snack and round trip
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North America
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Very Good95 reviews3.9
You must live this experience once in your life, This activity is only for travelers that love to be....
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Private Tour
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