Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 673 Sailing Trips activities in North America. Sort by Popularity. - Page 21Whale Shark Encounter Experience in Cancun (Snack Lunch included)
If you like awesome and unique activities, then this activity is for you. Welcome to the Whale Shark experience, this is a unique activity in the world and is the most enigmatic activity in Mexico. Imagine swimming next to an imme... More

Whale Shark Encounter Experience in Cancun (Snack Lunch included)
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North America
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Exellent4 reviews4.3
If you like awesome and unique activities, then this activity is for you. Welcome to the Whale Shark....
Private 2-Hour Morning Sail
Have you ever wanted to go sailing in the San Francisco Bay area but didn’t know anyone with a boat? Come sail with me, Captain John. Let me share my passion for sailing with you. I’m a U.S. certified sailing instructor and li... More
Private Tour

Private 2-Hour Morning Sail
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North America
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Superb5 reviews5
Have you ever wanted to go sailing in the San Francisco Bay area but didn’t know anyone with a boa....
Private Tour
Trimaran La Lupita,Sail Away to Isla Mujeres from Cancun
Sail away through Caribbean waters with the best crew in Cancun aboard "La Lupita.¨ Enjoy a spectacular day in the crystal-clear waters of the Mexican Caribbean, sailing from Cancun to Isla Mujeres on a boat full of fun, explorin... More
Private Tour

Trimaran La Lupita,Sail Away to Isla Mujeres from Cancun
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North America
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Very Good52 reviews4
Sail away through Caribbean waters with the best crew in Cancun aboard "La Lupita.¨ Enjoy a spectac....
Private Tour
Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay
We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We have made a commitment to sustainability and having a minimal impact on the environment ! It is a wholesome adventure that will le... More
Private Tour

Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay
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North America
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Superb10 reviews4.9
We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We ....
Private Tour
Waikiki Panorama Sail: Search for Hawaiian Sea Turtles
Snap beautiful photos of Waikiki on this 90-minute sail, where you'll cruise past famous Waikiki Beach and out towards Diamond Head crater. The cruise departs from Kewalo Basin by Ala Moana Beach Park, and includes snacks, non-alc... More
Private Tour

Waikiki Panorama Sail: Search for Hawaiian Sea Turtles
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North America
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Superb32 reviews4.7
Snap beautiful photos of Waikiki on this 90-minute sail, where you'll cruise past famous Waikiki Bea....
Private Tour
New York City Skyline Night Sailboat Tour
Step aboard a beautiful sailboat, Schooner America 2.0, for a relaxing city lights tour around New York. See the New York City skyline, the Statue of Liberty and Ellis Island lit up at night. Sit back and relax while enjoying a pe... More
Private Tour

New York City Skyline Night Sailboat Tour
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North America
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Superb9 reviews5
Step aboard a beautiful sailboat, Schooner America 2.0, for a relaxing city lights tour around New Y....
Private Tour
4 hrs Private Catamaran with Drinks Included
Our starting point is the iconic Chinese House with incredible views of the lagoon from its 360° lookout tower. Our friendly bilingual staff enlivens the tour with stories of the place and important facts about the local ecosyste... More
Private Tour

4 hrs Private Catamaran with Drinks Included
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North America
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Superb113 reviews4.9
Our starting point is the iconic Chinese House with incredible views of the lagoon from its 360° lo....
Private Tour
Oahu, Waikiki Sunset Catamaran Boat Tour
Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from December-March, of course, the annual humpback whales!... More
Private Tour

Oahu, Waikiki Sunset Catamaran Boat Tour
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North America
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Superb14 reviews4.9
Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (LÄ“â€....
Private Tour
Diamond Head Sunset Sail
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from the... More
Private Tour

Diamond Head Sunset Sail
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North America
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Superb15 reviews4.7
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....
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

Private Kelowna Sailing Cruise on Okanagan Lake
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North America
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Superb32 reviews5
Sailing is a quiet, peaceful experience, as the boat is powered by nothing but the wind. You are w....
Private Tour
Jolly Roger Pirate Show and Dinner Cruise with Open Bar
Spend you vacations' funniest evening along with Jolly Roger's flamboyant priate crew. Cruise along the Cancun coast while singing, drinking, dancing and participating in a variety of hilarious games and contests. The little pirat... More
Private Tour

Jolly Roger Pirate Show and Dinner Cruise with Open Bar
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North America
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Superb8 reviews4.6
Spend you vacations' funniest evening along with Jolly Roger's flamboyant priate crew. Cruise along ....
Private Tour
Private Catamaran from Cancun to Isla Mujeres | For up to 40 pp
Enjoy a day sailing through the Caribbean Sea aboard on a 46 ft Catamaran. Decide if you want to go on a trip to Isla Mujeres or just sail on the bay. Snorkel and discover the natural beauty of the great reefs of Cancun. Private... More
Private Tour

Private Catamaran from Cancun to Isla Mujeres | For up to 40 pp
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North America
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Exellent60 reviews4.2
Enjoy a day sailing through the Caribbean Sea aboard on a 46 ft Catamaran. Decide if you want to go....
Private Tour
Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelos
Join us for an unforgettable sailboat tour to the stunning Puerto Morelos Reef, a part of the Mesoamerican Barrier Reef System, the second-largest coral reef in the world! Departing daily at 9 AM and 2 PM, our adventure begins wit... 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 Good10 reviews3.7
Join us for an unforgettable sailboat tour to the stunning Puerto Morelos Reef, a part of the Mesoam....
Private Tour
Isla Mujeres Plus by Albatros Catamarans
Delight all your senses aboard a boat that will take you to one of the best islands in the world, swim in the impressive turquoise of the Mexican Caribbean, enjoy the delicacies of Mexican food, dance to Latin rhythms and forget a... More
Free Cancellation
Private Tour
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Isla Mujeres Plus by Albatros Catamarans
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North America
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Exellent305 reviews4.3
Delight all your senses aboard a boat that will take you to one of the best islands in the world, sw....
Free Cancellation
Private Tour
(Saving 7% )
San Diego Half-Day Marine Wildlife Tour with Lunch
Experience an exciting adventure while sailing along the San Diego coastline. Venture off into the Pacific Ocean and catch a chance to see local marine wildlife in its natural habitat, including sea lions, pelicans, and migrator... More
Private Tour

San Diego Half-Day Marine Wildlife Tour with Lunch
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North America
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Superb27 reviews4.8
Experience an exciting adventure while sailing along the San Diego coastline. Venture off into the P....
Private Tour
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
Private Tour

Hidden Beach - Marietas Islands
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North America
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Exellent42 reviews4.4
Spend the day exploring and enjoying the marine life of the Marietas Islands on this 5-hour excursio....
Private Tour
2 hours - Private Day Sail along Historic St Augustine Bayfront
We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to assist in making your experience a wonder memory. This 2-hour sail gives passengers a ... More
Private Tour

2 hours - Private Day Sail along Historic St Augustine Bayfront
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North America
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Superb16 reviews5
We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our sta....
Private Tour
Schooner Eastwind Sunset Sail to see the Maine Coastline
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goa... More
Private Tour

Schooner Eastwind Sunset Sail to see the Maine Coastline
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North America
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Exellent33 reviews4.5
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....
Private Tour

Private Sailing Tour of Bodega Bay
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North America
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Superb81 reviews4.8
This is a unique experience because you get to sail a 33' boat with a licensed captain. You can be i....
Private Tour
2 hours - Shared Sunset Sail along Historic St Augustine Bayfront
We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to assist in making your experience a wonder memory. This 2-hour sail gives passengers a ... More
Private Tour

2 hours - Shared Sunset Sail along Historic St Augustine Bayfront
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North America
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Superb6 reviews4.7
We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our sta....
Private Tour