Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 694 Sailing Trips activities in North America. Sort by Popularity. - Page 34Private Luxury Sailboat Charters of Honolulu
Oahu’s private luxury sailboat charter, Sailing Beauty, is operated by a mother and son team. While aboard this fully renovated 41' vessel, view the most treasured maritime life and landscapes of Oahu on a Day Sail and create gr... More
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Private Luxury Sailboat Charters of Honolulu
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North America
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Superb3 reviews5
Oahu’s private luxury sailboat charter, Sailing Beauty, is operated by a mother and son team. Whil....
Private Tour
Cancun to Isla Mujeres Full Day Tour with Snorkeling
Live a fun and relaxed day aboard a catamaran with open bar on board meeting the pearl of the Caribbean – Isla Mujeres, with its paradise beaches. We start the catamaran tour with national open bar included on board throughout ... More
Private Tour

Cancun to Isla Mujeres Full Day Tour with Snorkeling
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North America
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Superb3 reviews5
Live a fun and relaxed day aboard a catamaran with open bar on board meeting the pearl of the Carib....
Private Tour
Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guests
A Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sailing charters and boat tours. Sail San Diego with us. Our sa... More
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Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guest....
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North America
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Good2 reviews3.5
A Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San D....
Private Tour
Half-Day Luxury Sailing in Puerto Morelos with Open Bar
Set sail on the tranquil turquoise waters of Puerto Morelos aboard a luxury catamaran for an unforgettable half-day adventure. This experience offers a guided snorkeling session at a vibrant reef in the Mesoamerican Barrier Reef, ... More
Private Tour

Half-Day Luxury Sailing in Puerto Morelos with Open Bar
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North America
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Good2 reviews3.5
Set sail on the tranquil turquoise waters of Puerto Morelos aboard a luxury catamaran for an unforge....
Private Tour
Nighttime Sailing Trip from San Diego
Come aboard a 36-foot (11-meter) yacht for a nightcap on this 2-hour sailing trip from San Diego! Your knowledgeable captain and crew will take you past the Maritime Museum and the majestic city lights of San Diego. Whether you’... More
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Nighttime Sailing Trip from San Diego
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North America
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Good2 reviews3.5
Come aboard a 36-foot (11-meter) yacht for a nightcap on this 2-hour sailing trip from San Diego! Yo....
Private Tour
Private Sunset Sail for Two
Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise along the vibrant waterfront and marvel at the cityscape. Create a memory of a lifetime while sailing past Downtown, Point Loma, an... More
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Private Sunset Sail for Two
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North America
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Superb5 reviews5
Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise a....
Private Tour
Private Cruise Swim with Dolphin
Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and anniversaries. An Impressive Swimming Experience with Wild Dolphins at the West Coast of Oahu. Learning about the ecosystem of wil... More
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Private Cruise Swim with Dolphin
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North America
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Superb5 reviews5
Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and ....
Private Tour
Private Sightseeing Charter in Frenchman Bay
Enjoy a 2-hour tour of Frenchman Bay with eagle, seabird and porpoise sightings plus more. Explore the Porcupine Islands and Egg Rock. See beautiful views of Acadia National Park from the sea. Learn some history of coastal Maine a... More
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Private Sightseeing Charter in Frenchman Bay
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North America
Enjoy a 2-hour tour of Frenchman Bay with eagle, seabird and porpoise sightings plus more. Explore t....
Private Tour
Private Sunset Tour in Marina La Cruz by 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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Private Sunset Tour in Marina La Cruz by Yacht
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North America
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Superb17 reviews5
Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours do....
Private Tour

San Diego Private Boat Tour
Offering the BEST ‘one-of-a-kind’ ocean experience. Your invitation to what we call “CHAMPAGNE SAILING”! We offer the most spacious small group boat experience which includes a USCG Captain. Tell us your PARTY preferences ... More
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San Diego Private Boat Tour
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North America
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Superb17 reviews5
Offering the BEST ‘one-of-a-kind’ ocean experience. Your invitation to what we call “CHAMPAGNE....
Free Cancellation
Private Tour
(Saving 20% )
Public Schooner Sail in Greenport
You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see the East End of Long Island, and sailing aboard our unique schooner makes the experience extra special. U... More
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Public Schooner Sail in Greenport
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North America
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Superb1 review5
You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands d....
Private Tour
NY Yacht Cruise with High Couture Show, Art Exhibit & Appetizers
- VIP access to "The Haute Couture Boat" event. - Firsthand viewing of Empório Aragão's new collection launch. - Showcase of 7 other international designers' collections. - Access to "Art Biennale sur Mer" art exhibition by São... More
Private Tour

NY Yacht Cruise with High Couture Show, Art Exhibit & Appetizers
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North America
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Superb4 reviews5
- VIP access to "The Haute Couture Boat" event. - Firsthand viewing of Empório Aragão's new collec....
Private Tour
2 Hours Small Group Fireworks Night in Waikiki
Enjoy a relaxing sail to Diamond head and Experience an unforgettable evening with Friday fireworks in small intimate group . See this vibrant display from a whole new perspective as the colorful lights reflect off the sea. Kick b... More
Private Tour

2 Hours Small Group Fireworks Night in Waikiki
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North America
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Superb4 reviews5
Enjoy a relaxing sail to Diamond head and Experience an unforgettable evening with Friday fireworks ....
Private Tour
Kanoa Yacht Charter: 2-Hour Sail off Waikiki
Start your luxurious voyage at Kewalo Basin Harbor, located at 1025 Ala Moana Blvd - Pier E, Slip 223. With prime parking on-site, your journey begins the moment you arrive. For those without wheels, don't fret! The dock is a quic... More
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Kanoa Yacht Charter: 2-Hour Sail off Waikiki
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North America
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Superb4 reviews5
Start your luxurious voyage at Kewalo Basin Harbor, located at 1025 Ala Moana Blvd - Pier E, Slip 22....
Private Tour
Private Catamaran from Cancun to Isla Mujeres | For up to 100 pp
Experience the Caribbean like never before with our sophisticated seafarer guiding you through its pristine waters. During this tour, you will have one snorkel stop at any of the following places: El meco, Sac Bajo, El Farito, or... More
Private Tour

Private Catamaran from Cancun to Isla Mujeres | For up to 100 pp
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North America
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Superb18 reviews4.8
Experience the Caribbean like never before with our sophisticated seafarer guiding you through its p....
Private Tour
SSS Experience. Speedboat, Snorkel, and Sightseeing in Cancun, Must Do Activity
Welcome to the most intrepid and extreme adventure in Cancún. You will be able to known the other face of the Caribbean with the Jungle Tour. On this activity we will drive our speedboat through the calm waters of the Nichupte... More
Private Tour

SSS Experience. Speedboat, Snorkel, and Sightseeing in Cancun, Mu....
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North America
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Superb18 reviews4.8
Welcome to the most intrepid and extreme adventure in Cancún. You will be able to known the other f....
Private Tour
It doesn't get better than this all inclusive 95ft luxury yacht
This all inclusive Baller Package isn't for everyone. If you want THE luxury yacht in Cabo this 95ft is THE one. Hot tub, bedrooms, bathrooms, we are talking 95ft baller baby! Contact us directly to make sure we can get you the ex... More
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It doesn't get better than this all inclusive 95ft luxury yacht
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North America
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Superb18 reviews4.8
This all inclusive Baller Package isn't for everyone. If you want THE luxury yacht in Cabo this 95ft....
Private Tour
Lowcountry Boil Dinner Cruise
Step aboard Bonjour for a one of a kind dinner cruise where Southern flavor meets coastal charm. Feast on a hearty Lowcountry Boil—piled high with fresh shrimp, sausage, corn, and potatoes—all while cruising the scenic waters ... More
Private Tour

Lowcountry Boil Dinner Cruise
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North America
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Superb18 reviews4.8
Step aboard Bonjour for a one of a kind dinner cruise where Southern flavor meets coastal charm. Fea....
Private Tour
Lana'i Coast Snorkel and Sail
Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as we explore and snorkel the incredible coastline of Maui. We'll check the conditions for the day and take off across the channel o... More
Private Tour

Lana'i Coast Snorkel and Sail
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North America
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Superb18 reviews4.8
Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as....
Private Tour
Two Hour Private Sailing Charter
Escape the city on a two hour private sailing charter for up to 6 guests. Our two hour charter option is available morning, afternoon, and evening, and it is a great option for a quick getaway. We sail you around lower Manhattan w... More
Private Tour

Two Hour Private Sailing Charter
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North America
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Superb3 reviews5
Escape the city on a two hour private sailing charter for up to 6 guests. Our two hour charter optio....
Private Tour