Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 680 Sailing Trips activities in North America. Sort by Popularity. - Page 34Private Atomic Catamaran Tour to Isla Mujeres
By booking this private service, you can design a completely tailored itinerary. You will have the freedom to navigate to the places of your choice for 7 hours. In addition, you can decide the length of stay at each of the suggest... More
Private Tour

Private Atomic Catamaran Tour to Isla Mujeres
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North America
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Superb1 review5
By booking this private service, you can design a completely tailored itinerary. You will have the f....
Private Tour
Waikiki Sunset Cruise and Iconic Views with Swimming
Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide along the iconic Gold Coast as the sun sets, painting the sky with vibrant co... More
Free Cancellation
Private Tour
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Waikiki Sunset Cruise and Iconic Views with Swimming
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North America
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Superb1 review5
Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in....
Free Cancellation
Private Tour
(Saving 20% )
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
Private Tour

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 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
Small Group Sunset Sail in San Diego
Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perfect for solo travelers, couples, or friends looking to experience the bay from the water without booking a private charter. Relax... More
Private Tour

Small Group Sunset Sail in San Diego
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North America
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Superb30 reviews5
Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perf....
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
Private Tour

It doesn't get better than this all inclusive 95ft luxury yacht
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North America
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Superb30 reviews5
This all inclusive Baller Package isn't for everyone. If you want THE luxury yacht in Cabo this 95ft....
Private Tour
Private 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
Private Tour

Private Luxury Sailboat Charters of Honolulu
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North America
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Superb30 reviews5
Oahu’s private luxury sailboat charter, Sailing Beauty, is operated by a mother and son team. Whil....
Private Tour
Private Sailboat Hakuna, 4hr Adventure, Snorkeling and Beach Club
WELCOME to Mayan Paradise!!!! We are Liz (Biologist) and Danny (Sustainable Sailing) and we will guide you on this wonderful route created for you and your companions (Adventure Tourism, Nature and more). You are looking for TRA... More
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(Saving 5% )

Private Sailboat Hakuna, 4hr Adventure, Snorkeling and Beach Club
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North America
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Superb7 reviews5
WELCOME to Mayan Paradise!!!! We are Liz (Biologist) and Danny (Sustainable Sailing) and we will gu....
Free Cancellation
Private Tour
(Saving 5% )
Nights of Lights Sailboat Tour St Augustine Sailing
What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours offer a simple ride, St Augustine Sailing provides an intimate, serene setting ... More
Private Tour

Nights of Lights Sailboat Tour St Augustine Sailing
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North America
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Superb3 reviews5
What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experien....
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
Rosé Brunch Under Sail
Wake up with our daily Brunch Under Sail aboard a luxury catamaran. Cruise through the calm morning waters of Hilton Head while enjoying complimentary mimosas and light brunch bites. This relaxing 2-hour sail is the perfect blend ... More
Private Tour

Rosé Brunch Under Sail
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North America
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Superb17 reviews5
Wake up with our daily Brunch Under Sail aboard a luxury catamaran. Cruise through the calm morning ....
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
Private Tour

Private Cruise Swim with Dolphin
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North America
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Superb17 reviews5
Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and ....
Private Tour
Pirate Ship by Day
Start the day enjoying a delicious and complete breakfast Under the Sea, in our Pirate Tavern, aboard an incredible 700-ton Galleon, full of adventure and fun. Let yourself be pampered by nature on Majahuitas Island (Ecological R... More
Private Tour

Pirate Ship by Day
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North America
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Good5 reviews3.4
Start the day enjoying a delicious and complete breakfast Under the Sea, in our Pirate Tavern, aboar....
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
Private Tour

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 3 hour Bird Watching Tour in Monterey Bay
Enjoy a 3 hour cruise to search for and see local seabirds of the Monterey Bay. A vessel under sail is much quieter and therefore up close encounters with seabirds are common. This tour is great for birders who are looking for an ... More
Private Tour

Private 3 hour Bird Watching Tour in Monterey Bay
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North America
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Superb1 review5
Enjoy a 3 hour cruise to search for and see local seabirds of the Monterey Bay. A vessel under sail ....
Private Tour
Private Yacht for up to 12 People
Imagine feeling the sea breeze aboard the wonderful Tiara 44 Yacht, it will definitely be a trip that you will enjoy like no other, you cannot miss its comfortable spaces while the beautiful colors of the sea and the sky make thos... More
Private Tour

Private Yacht for up to 12 People
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North America
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Superb1 review5
Imagine feeling the sea breeze aboard the wonderful Tiara 44 Yacht, it will definitely be a trip tha....
Private Tour
Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay
This is the most hands-on sailing experience in Miami. As soon as you get in the boat you become part of the crew. Our goal is to perform as a unit and get the boat to sail as fast as possible. However, if you are looking for a mo... More
Private Tour

Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay
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North America
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Superb1 review5
This is the most hands-on sailing experience in Miami. As soon as you get in the boat you become par....
Private Tour
Private Tour of Laguna de Bacalar Full Day
If you need to disconnect from the daily rhythm and immerse yourself in the tranquility of nature, let us take you to discover the best kept secrets of the lagoon of Bacalar. Our expert captains will guide you aboard a sailboat th... More
Private Tour

Private Tour of Laguna de Bacalar Full Day
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North America
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Superb1 review5
If you need to disconnect from the daily rhythm and immerse yourself in the tranquility of nature, l....
Private Tour
Puerto Vallarta Private Sailing Trip with Beer and Ceviche
Live a Unique Sailing Experience in Puerto Vallarta - Step aboard a beautifully restored classic sailboat for a private journey along the stunning Banderas Bay. Designed for groups of up to 14 people (with the option to add more g... More
Private Tour

Puerto Vallarta Private Sailing Trip with Beer and Ceviche
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North America
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Superb1 review5
Live a Unique Sailing Experience in Puerto Vallarta - Step aboard a beautifully restored classic sai....
Private Tour
Classic Private Tour of the Lagoon of Bacalar
Ready to unplug and get carried away with the magic of Bacalar? Hop on one of the sailboats and let the wind and expert sailors guide you through the most stunning corners of the Seven Colors Lagoon. Sail over crystal clear waters... More
Private Tour

Classic Private Tour of the Lagoon of Bacalar
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North America
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Superb1 review5
Ready to unplug and get carried away with the magic of Bacalar? Hop on one of the sailboats and let ....
Private Tour