Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 725 Sailing Trips activities in North America. Sort by Popularity. - Page 13Half Day Luxury Sailing Experience in Riviera Maya with Open Bar
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so that makes the experience better. The snorkeling is amazing, as you will see much colorful fish, st... More

Half Day Luxury Sailing Experience in Riviera Maya with Open Bar
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North America
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Exellent66 reviews4.4
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....
Isla Mujeres Sailing Adventure from Cancun
Join the experience of sailing through the Mexican Caribbean Sea from Cancun to Isla Mujeres onboard of an exclusive catamaran...!! This tour is recommended for those who like to have fun, with music for all tastes and open-bar on... More

Isla Mujeres Sailing Adventure from Cancun
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North America
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Very Good6 reviews3.7
Join the experience of sailing through the Mexican Caribbean Sea from Cancun to Isla Mujeres onboard....
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
Free Cancellation
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Sailing Tour through the Lagoon of the 7 Colors
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North America
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Superb1,096 reviews4.9
Sail with people who share your passion for adventure! You will explore fascinating places along the....
Free Cancellation
(Saving 15% )
City Tour & Beach Club All Inclusive W Horse Ride & Water Sports
Experience the ultimate vacation with our all-inclusive tour! Sit back and relax as you are transported in a luxurious, air-conditioned vehicle, complete with complimentary beverages. Our tour includes visits to the stunning cathe... More

City Tour & Beach Club All Inclusive W Horse Ride & Water Sports
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North America
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Good3 reviews3.3
Experience the ultimate vacation with our all-inclusive tour! Sit back and relax as you are transpor....
Small-Group San Diego Afternoon Sailing Excursion
This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five friends and fill up the whole boat!). Sit back, relax and enjoy the com... More

Small-Group San Diego Afternoon Sailing Excursion
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North America
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Superb525 reviews5
This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing....
Sunset Sail Tour
Take a 2.0 hour sailing cruise on a Sparkman and Stephens Sailing Yacht. With your small-group, engage on this classic 42 ft yacht, that accommodates a 6 passenger maximum for an intimate cruise through the waters of Wrightsvill... More

Sunset Sail Tour
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North America
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Superb88 reviews4.9
Take a 2.0 hour sailing cruise on a Sparkman and Stephens Sailing Yacht. With your small-group, enga....
New York Fall Foliage Sail up the Hudson River
Enjoy a 3.5-hour scenic sail up the Hudson River to the Palisades aboard Schooner Adirondack or Schooner America 2.0, both 1800s-style sailboats. Bordering the Hudson River north of Fort Lee, New Jersey, the Palisade Cliffs are am... More

New York Fall Foliage Sail up the Hudson River
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North America
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Exellent8 reviews4.5
Enjoy a 3.5-hour scenic sail up the Hudson River to the Palisades aboard Schooner Adirondack or Scho....
Schooner Clearwater- Sailing Cruise-Clearwater Beach
Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Parti... More

Schooner Clearwater- Sailing Cruise-Clearwater Beach
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North America
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Superb217 reviews4.9
Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater wi....
New York City Sunset Sail to the Statue of Liberty
Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic sailboat is 105-feet in length and has about 3600 square feet of sail ... More

New York City Sunset Sail to the Statue of Liberty
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North America
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Superb65 reviews4.9
Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of B....
Casco Bay: Private Afternoon Charter on Heart's Desire
This two-hour afternoon private cruise is the perfect way to experience Maine's coast, your special event, or a family get-together that will never be forgotten. Ride aboard Heart's Desire: designed by famed yacht designer - John... More
Private Tour

Casco Bay: Private Afternoon Charter on Heart's Desire
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North America
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Very Good1 review4
This two-hour afternoon private cruise is the perfect way to experience Maine's coast, your special ....
Private Tour

Tulum: Snorkeling and Private Sailing Tour
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North America
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Superb155 reviews4.9
We will enjoy a wonderful catamaran tour, powered only by the wind, we will be able to enjoy a spect....
Private Tour
2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More
Private Tour

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People
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North America
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Superb14 reviews4.8
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour
Private Sunset Sail for 3-6 People
Experience a private group charter with up to six passengers while sailing along the San Diego Bay. If you’re looking for a night of family fun, or to celebrate with your friends look no further. Leave your worries behind as yo... More
Private Tour

Private Sunset Sail for 3-6 People
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North America
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Superb12 reviews4.7
Experience a private group charter with up to six passengers while sailing along the San Diego Bay.....
Private Tour
Hawaiian Canoe Sailing Experience in Maui
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More
Private Tour

Hawaiian Canoe Sailing Experience in Maui
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North America
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Superb58 reviews4.8
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....
Private Tour
2 Island Adventure: Contoy & Mujeres with Snorkeling & open bar
What makes this tour unique? Unlike most tours that visit only one island, our experience takes you to two stunning Caribbean islands in a single day—Isla Contoy, a protected ecological reserve with limited daily visitors, and t... More
Private Tour

2 Island Adventure: Contoy & Mujeres with Snorkeling & open bar
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North America
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Exellent6 reviews4.3
What makes this tour unique? Unlike most tours that visit only one island, our experience takes you ....
Private Tour
San Diego Afternoon Sail
Join Captain Doyle for an unforgettable 2-hour sailing experience aboard our 35-foot sailboat, Luna. Enjoy wide-open views of the city's skyline and waterfront attractions as we sail among tall ships, mega-yachts, and military ves... More
Private Tour

San Diego Afternoon Sail
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North America
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Superb9 reviews5
Join Captain Doyle for an unforgettable 2-hour sailing experience aboard our 35-foot sailboat, Luna.....
Private Tour
Waikiki small group turtle snorkeling & sailing
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of dawn during their Hawaiian vacation due to time zone changes. As we start out our tour from ... More
Private Tour

Waikiki small group turtle snorkeling & sailing
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North America
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Superb78 reviews5
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....
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

Catamaran Sailing Cruise in Monterey
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North America
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Superb27 reviews4.7
Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage af....
Private Tour

Private 2-Hour Sunset Sailing Tour on Lake Fairview
Sunset Sailing Tour in Orlando | The Perfect Date Night Experience! Looking for something different to do in Orlando besides theme parks? Escape the crowds and experience the hidden beauty of Central Florida with an unforgettabl... More
Free Cancellation
Private Tour
(Saving 15% )

Private 2-Hour Sunset Sailing Tour on Lake Fairview
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North America
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Superb32 reviews5
Sunset Sailing Tour in Orlando | The Perfect Date Night Experience! Looking for something differen....
Free Cancellation
Private Tour
(Saving 15% )
12pm Turtle Canyon Snorkel Adventure
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More
Private Tour

12pm Turtle Canyon Snorkel Adventure
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North America
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Superb298 reviews4.8
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
Private Tour