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Top 10 Best North America Sailing Trips

Found 671 Sailing Trips activities in North America. Sort by Popularity. - Page 32
 

Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres

(4.9 of 9 reviews)

A Caribbean Escape Like No Other! Experience the beauty of the Caribbean on this all-inclusive catamaran tour from Cancun to Isla Mujeres. The day begins with a leisurely sail across the turquoise waters, where you'll enjoy drinks... More

Free Cancellation
Start From $79.00
 
Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres Likely to Sell Out

Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres

  • North America
  • Superb9 reviews4.9

A Caribbean Escape Like No Other! Experience the beauty of the Caribbean on this all-inclusive catam....

    Free Cancellation
    Start From $79.00
 
 

Key West Haunted Night Sail on Schooner America 2.0

(4.9 of 9 reviews)

Join us aboard Schooner America 2.0 for a night sail with haunting nautical tales come to life under the Key West night sky. During this night boat ride, we'll cruise through the waters of Key West while listening to mysterious t... More

Free Cancellation
Start From $88.15
 
Key West Haunted Night Sail on Schooner America 2.0 Likely to Sell Out

Key West Haunted Night Sail on Schooner America 2.0

  • North America
  • Superb9 reviews4.9

Join us aboard Schooner America 2.0 for a night sail with haunting nautical tales come to life under....

    Free Cancellation
    Start From $88.15
 
 

Private Cancun Sailboat Cruise with Beers and Sodas Included

(4.9 of 9 reviews)

Escape to paradise with our exclusive private sailing boat cruise to Isla Mujeres, a pristine island gem just off the coast of Cancun. Step aboard our fine vessel and embark on a journey of discovery and relaxation in the breathta... More

Free Cancellation
Private Tour
Start From $579.00
 
Private Cancun Sailboat Cruise with Beers and Sodas Included Likely to Sell Out

Private Cancun Sailboat Cruise with Beers and Sodas Included

  • North America
  • Superb9 reviews4.9

Escape to paradise with our exclusive private sailing boat cruise to Isla Mujeres, a pristine island....

    Free Cancellation
    Private Tour
    Start From $579.00
 
 

Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay

(4.9 of 9 reviews)

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

Free Cancellation
Private Tour
Start From $600.00
 
Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay Likely to Sell Out

Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay

  • North America
  • Superb9 reviews4.9

This is the most hands-on sailing experience in Miami. As soon as you get in the boat you become par....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

Bimini Charters - Private 6 Hour catamaran sail & snorkel

(4.9 of 9 reviews)

We are owner-operated and ensure every detail of your trip is perfect! We work with you ahead of time to determine your goals for the day and make them happen. Our guests almost always say that their trip with us was the highlight... More

Free Cancellation
Private Tour
Start From $1,400.00
 
Bimini Charters - Private 6 Hour catamaran sail & snorkel Likely to Sell Out

Bimini Charters - Private 6 Hour catamaran sail & snorkel

  • North America
  • Superb9 reviews4.9

We are owner-operated and ensure every detail of your trip is perfect! We work with you ahead of tim....

    Free Cancellation
    Private Tour
    Start From $1,400.00
 
 

Private Charter Snorkel Sail Adventure off Kaanapali Beach

(4.9 of 9 reviews)

PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘H... More

Free Cancellation
Private Tour
Start From $6,301.24
 
Private Charter Snorkel Sail Adventure off Kaanapali Beach Likely to Sell Out

Private Charter Snorkel Sail Adventure off Kaanapali Beach

  • North America
  • Superb9 reviews4.9

PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant wi....

    Free Cancellation
    Private Tour
    Start From $6,301.24
 
 

Private Sightseeing Charter in Frenchman Bay

(3 of 2 reviews)

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

Free Cancellation
Private Tour
Start From $700.00
 
Private Sightseeing Charter in Frenchman Bay Likely to Sell Out

Private Sightseeing Charter in Frenchman Bay

  • North America

Enjoy a 2-hour tour of Frenchman Bay with eagle, seabird and porpoise sightings plus more. Explore t....

    Free Cancellation
    Private Tour
    Start From $700.00
 
 

Monday Ladies Night Sail- Charleston's Luxury Catamaran w/Bar

(3 of 2 reviews)

Mermaid Monday Ladies’ Night Sail: Fun, Friends & Fabulous Harbor Views Calling all ladies! Mermaid Monday is Charleston’s hottest ladies' night, and you’re invited to join the fun. With $10 off regular tickets and irresisti... More

Free Cancellation
Private Tour
Start From $50.00
 
Monday Ladies Night Sail- Charleston's Luxury Catamaran w/Bar Likely to Sell Out

Monday Ladies Night Sail- Charleston's Luxury Catamaran w/Bar

  • North America

Mermaid Monday Ladies’ Night Sail: Fun, Friends & Fabulous Harbor Views Calling all ladies! Mermai....

    Free Cancellation
    Private Tour
    Start From $50.00
 
 

Private Long Island Sound Sailing Experience

(3 of 2 reviews)

Sail the Long Island Sound with Captain Steve. Sit back and relax as we tour Manhasset Bay, nestled between Great Neck's Kings Point and Port Washington's Sands Point. Oogle at the multi million dollar Mansions lining the coast un... More

Free Cancellation
Private Tour
Start From $650.00
 
Private Long Island Sound Sailing Experience Likely to Sell Out

Private Long Island Sound Sailing Experience

  • North America

Sail the Long Island Sound with Captain Steve. Sit back and relax as we tour Manhasset Bay, nestled ....

    Free Cancellation
    Private Tour
    Start From $650.00
 
 

Come experience a 3 hour Private Sail in Sidney BC Canada

(3 of 2 reviews)

We provide a memorable 3 hour sailing adventure, on our safe, comfortable Hunter 35.5 yacht, which may include possible sightings of orca whales, eagles, seals, and porpoises. Guests are welcome to help as much or as little as th... More

Free Cancellation
Private Tour
Start From $124.84
 
Come experience a 3 hour Private Sail in Sidney BC Canada Likely to Sell Out

Come experience a 3 hour Private Sail in Sidney BC Canada

  • North America

We provide a memorable 3 hour sailing adventure, on our safe, comfortable Hunter 35.5 yacht, which m....

    Free Cancellation
    Private Tour
    Start From $124.84
 
 

All Inclusive Private: 40´ Yacht Van Dutch El Cielo Cozumel

(4.8 of 22 reviews)

It is a private experience with a super fast luxury yacht that will take you to the incredible island of Cozumel to visit the biosphere of Heaven and delight yourself with exclusive dishes created just for you... More

Free Cancellation
Private Tour
Start From $3,200.00
 
All Inclusive Private: 40´ Yacht Van Dutch El Cielo Cozumel Likely to Sell Out

All Inclusive Private: 40´ Yacht Van Dutch El Cielo Cozumel

  • North America
  • Superb22 reviews4.8

It is a private experience with a super fast luxury yacht that will take you to the incredible islan....

    Free Cancellation
    Private Tour
    Start From $3,200.00
 
 

VIP Sailing Experience Puerto Vallarta

(5 of 11 reviews)

Choose between an afternoon stroll, a refreshing splash in the water or a sunbathing siesta with your toes in the sand. Ada Sailing provides masks, snorkels, fins and life jackets for children and adults. This tour is only availab... More

Free Cancellation
Private Tour
Start From $169.78
 
VIP Sailing Experience Puerto Vallarta Likely to Sell Out

VIP Sailing Experience Puerto Vallarta

  • North America
  • Superb11 reviews5

Choose between an afternoon stroll, a refreshing splash in the water or a sunbathing siesta with you....

    Free Cancellation
    Private Tour
    Start From $169.78
 
 

Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guests

(3.5 of 2 reviews)

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

Free Cancellation
Private Tour
Start From $600.00
 
Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guests Likely to Sell Out

Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guest....

  • North America
  • Good2 reviews3.5

A Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San D....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

Private Yacht for up to 12 People

(3.5 of 2 reviews)

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

Free Cancellation
Private Tour
Start From $2,030.00
 
Private Yacht for up to 12 People Likely to Sell Out

Private Yacht for up to 12 People

  • North America
  • Good2 reviews3.5

Imagine feeling the sea breeze aboard the wonderful Tiara 44 Yacht, it will definitely be a trip tha....

    Free Cancellation
    Private Tour
    Start From $2,030.00
 
 

Banderas Bay Sailing adventure Private Sailboat

(3.5 of 2 reviews)

Join an unforgettable sailing experience led by a captain who has single handily crossed the Pacific 4 times! You’ll explore the breathtaking beauty of Banderas Bay in comfort and style aboard a 40 foot sloop. Private charter lu... More

Free Cancellation
Private Tour
Start From $874.63
 
Banderas Bay Sailing adventure Private Sailboat Likely to Sell Out

Banderas Bay Sailing adventure Private Sailboat

  • North America
  • Good2 reviews3.5

Join an unforgettable sailing experience led by a captain who has single handily crossed the Pacific....

    Free Cancellation
    Private Tour
    Start From $874.63
 
 

Pirate Ship by Day

(3.4 of 5 reviews)

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

Free Cancellation
Private Tour
Start From $280.00
 
Pirate Ship by Day Likely to Sell Out

Pirate Ship by Day

  • North America
  • Good5 reviews3.4

Start the day enjoying a delicious and complete breakfast Under the Sea, in our Pirate Tavern, aboar....

    Free Cancellation
    Private Tour
    Start From $280.00
 
 

4th of July Sunset Sail on the Black Pearl

(3.4 of 5 reviews)

Join us for the 4th of July for Fireworks over Cedar Point from a beautiful 47' Sailing yacht - The Black Pearl! Sail magestically across the water as we find our most perfect spot for viewing the fireworks while watching the suns... More

Free Cancellation
Private Tour
Start From $1,195.00
 
4th of July Sunset Sail on the Black Pearl Likely to Sell Out

4th of July Sunset Sail on the Black Pearl

  • North America
  • Good5 reviews3.4

Join us for the 4th of July for Fireworks over Cedar Point from a beautiful 47' Sailing yacht - The ....

    Free Cancellation
    Private Tour
    Start From $1,195.00
 
 

Private Morning Ceremony Sailing Charter

(3.4 of 5 reviews)

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, and more. We offer this experience at a discounted rate to accommodate groups wanting to do private charters in the morning to celeb... More

Free Cancellation
Private Tour
Start From $1,000.00
 
Private Morning Ceremony Sailing Charter Likely to Sell Out

Private Morning Ceremony Sailing Charter

  • North America
  • Good5 reviews3.4

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, an....

    Free Cancellation
    Private Tour
    Start From $1,000.00
 
 

3-Night Private Charter in Lake Clark National Park

(5 of 2 reviews)

An exciting private adventure exploring Lake Clark in the luxury of our 50ft sailing catamaran, the only live aboard yacht on Lake Clark. Enjoy meals prepared by your onboard chef. Relax in our beanbags and hammocks while enjoyin... More

Free Cancellation
Private Tour
Start From $17,000.00
 
3-Night Private Charter in Lake Clark National Park Likely to Sell Out

3-Night Private Charter in Lake Clark National Park

  • North America
  • Superb2 reviews5

An exciting private adventure exploring Lake Clark in the luxury of our 50ft sailing catamaran, the ....

    Free Cancellation
    Private Tour
    Start From $17,000.00
 
 

Key West Wreckers Race Aboard Schooner America 2.0

(4.9 of 9 reviews)

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in the day, pirate ships from afar often ran aground on Sand Key Reef, nine miles off the southern ... More

Free Cancellation
Private Tour
Start From $111.80
 
Key West Wreckers Race Aboard Schooner America 2.0 Likely to Sell Out

Key West Wreckers Race Aboard Schooner America 2.0

  • North America
  • Superb9 reviews4.9

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse abo....

    Free Cancellation
    Private Tour
    Start From $111.80
 
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