Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 672 Sailing Trips activities in North America. Sort by Popularity. - Page 12Windjammer 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

Windjammer Classic Day Sail from Camden, Maine
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North America
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Superb335 reviews4.7
See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....
Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch
Let yourself be carried away by the wind on an unforgettable adventure through the wonderful Lagoon of 7 Colors. A unique experience to enjoy with family or friends, open bar and lunch. Without engine noises, the sounds of nature... More

Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch
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North America
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Superb41 reviews4.9
Let yourself be carried away by the wind on an unforgettable adventure through the wonderful Lagoon ....
Waikiki Sail and Snorkel Adventure Best of Hawaii 2023
Immerse yourself in a vibrant underwater wonderland as you snorkel through coral reefs teeming with an array of tropical fish. The clear waters of Turtle Canyons reveal a kaleidoscope of colors, from dazzling schools of fish to vi... More
Private Tour

Waikiki Sail and Snorkel Adventure Best of Hawaii 2023
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North America
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Very Good4 reviews4
Immerse yourself in a vibrant underwater wonderland as you snorkel through coral reefs teeming with ....
Private Tour
Private Sunset Sailing Cruise in Puerto Vallarta
On this sunset sailing experience you will be able to apreciate a relaxing sunset while you take on stunning views of the Sierra Madre mountains and the prettiest areas of Down Town Puerto Vallarta. While on tour we provide 2 cour... More
Private Tour

Private Sunset Sailing Cruise in Puerto Vallarta
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North America
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Superb22 reviews5
On this sunset sailing experience you will be able to apreciate a relaxing sunset while you take on ....
Private Tour
Private Charter
The captain works with the guest to design a custom outing based on his 30 years of cruising experience in the local area. With knowledge of the local sea conditions and coastal ecology. you build a custom experience. Typically, G... More
Private Tour

Private Charter
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North America
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Superb12 reviews4.8
The captain works with the guest to design a custom outing based on his 30 years of cruising experie....
Private Tour
Fort Lauderdale Sailing Charter
Your PRIVATE or SEMI-PRIVATE sailboat charter is hosted by Captain Dan, a licensed captain with 20 years of local sailing experience. For PRIVATE charters, call directly to make arrangements. One to Three passengers bookings are s... More
Private Tour

Fort Lauderdale Sailing Charter
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North America
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Superb359 reviews5
Your PRIVATE or SEMI-PRIVATE sailboat charter is hosted by Captain Dan, a licensed captain with 20 y....
Private Tour
The Boat People Cruise Private Harbor Cruises
Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We strive to create an unforgettable evening with contagious laughter and panoramic views of the Newport Bay. Bring your plus one or ... More
Private Tour

The Boat People Cruise Private Harbor Cruises
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North America
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Superb27 reviews5
Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We ....
Private Tour
Kayak + Guided Snorkel & Morning Sail hosted by Honest Eco
I founded and own HONEST ECO. With Kentucky bluegrass roots and a B.S. in Biology, I found a world with a blue sea too alluring to ignore. I arrived to Key West in 2005. Now I have 10+ years of experience studying Biology and bein... More
Private Tour

Kayak + Guided Snorkel & Morning Sail hosted by Honest Eco
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North America
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Superb153 reviews5
I founded and own HONEST ECO. With Kentucky bluegrass roots and a B.S. in Biology, I found a world w....
Private Tour
Jolly Roger Pirate Ship Cruise & Dinner Show
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 Ship Cruise & Dinner Show
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North America
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Superb6 reviews5
Become a pirate for a night by teaming up with Jolly Roger's cheerful crew! Embark on a fun-packed s....
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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Superb4 reviews4.8
Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. Th....
Private Tour
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
Private Tour

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....
Private Tour
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
Private Tour

Luxury Catamaran tour to isla mujeres with transportation from Tu....
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North America
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Good62 reviews3.5
Excellent service on board Professional crew members Safety measures in all our activities Sanitary ....
Private Tour
San Salvador Spanish Galleon Adventure Day Sail with General Admission
Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step on board this 16th century Spanish galleon. The San Salvador is a replica of Juan Rodriguez Cabrillo’s ship that arrived at the ... More
Private Tour

San Salvador Spanish Galleon Adventure Day Sail with General Admi....
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North America
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Exellent2 reviews4.5
Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step o....
Private Tour
Newport Sunset Sail on Schooner Adirondack
Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailbo... More
Private Tour

Newport Sunset Sail on Schooner Adirondack
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North America
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Superb36 reviews4.9
Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of th....
Private Tour
Molokini Snorkel and Performance Sail from Ma'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

Molokini Snorkel and Performance Sail from Ma'alaea Harbor
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North America
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Superb198 reviews4.9
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
Private Tour
Sunset Sail from Traverse City with Food, Wine & Cocktails
Wind down and relax as our captain and crewmates teach you about our elegant schooner and share stories about the history of the lands, people, and waters of the Grand Traverse Bay area. Enjoy complimentary locally sourced food, w... More
Private Tour

Sunset Sail from Traverse City with Food, Wine & Cocktails
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North America
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Superb177 reviews4.8
Wind down and relax as our captain and crewmates teach you about our elegant schooner and share stor....
Private Tour
Newport Sunset Sail on Classic Sailboat
Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailboat and see all of Newport's iconic sights from the water including histor... More
Private Tour

Newport Sunset Sail on Classic Sailboat
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North America
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Superb17 reviews4.8
Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a ....
Private Tour
Monterey Private 3 - 4 Hour Whale Watching Cruise
Enjoy a 3 - 4 hour sailing cruise on the Monterey Bay. This Marine Mammal and Wildlife Safari is a private guided tour and can accommodate up to 6 people. Whale sightings are NOT guaranteed. However, this tour is designed to give... More
Private Tour

Monterey Private 3 - 4 Hour Whale Watching Cruise
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North America
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Superb2 reviews5
Enjoy a 3 - 4 hour sailing cruise on the Monterey Bay. This Marine Mammal and Wildlife Safari is a p....
Private Tour

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
Free Cancellation
Private Tour
(Saving 20% )

12pm Turtle Canyon Snorkel Adventure
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North America
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Superb274 reviews4.8
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
Free Cancellation
Private Tour
(Saving 20% )
4 hours Sailboat Tour for 2 people along the Los Angeles Coastline
The coastal line of Los Angeles. You will see Marina Del Rey, head for Santa Monica, sail past Venice Beach, Airport, Malibu beach, go into the open ocean, anchor (if desired) and return back to Marina Del Rey.... More
Private Tour

4 hours Sailboat Tour for 2 people along the Los Angeles Coastlin....
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North America
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Very Good3 reviews3.7
The coastal line of Los Angeles. You will see Marina Del Rey, head for Santa Monica, sail past Venic....
Private Tour