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Top 10 Best North America Sailing Trips

Found 754 Sailing Trips activities in North America. Sort by Popularity. - Page 24
 

Cozumel All Inclusive: Coast & Relax 4h on 51' Leopard

(5 of 38 reviews)

Situated in the azure waters of the Mexican Caribbean, Cozumel stands as a jewel of unparalleled beauty. Recognized as Mexico's largest island, it draws travelers with its captivating charm and natural wonders. Diving enthusiasts ... More

Free Cancellation
Private Tour
Start From $3,650.00
 
Cozumel All Inclusive: Coast & Relax 4h on 51' Leopard

Cozumel All Inclusive: Coast & Relax 4h on 51' Leopard

  • North America
  • Superb38 reviews5

Situated in the azure waters of the Mexican Caribbean, Cozumel stands as a jewel of unparalleled bea....

    Free Cancellation
    Private Tour
    Start From $3,650.00
 
 

Pastries & Prosecco Aboard a Tall Ship in Boston Harbor

(5 of 14 reviews)

What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable views of the city. Your ticket includes complimentary coffee and fresh-baked pastries from the incomparable Flour Bakery + Cafe. F... More

Free Cancellation
Private Tour
Start From $84.75
 
Pastries & Prosecco Aboard a Tall Ship in Boston Harbor

Pastries & Prosecco Aboard a Tall Ship in Boston Harbor

  • North America
  • Superb14 reviews5

What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable v....

    Free Cancellation
    Private Tour
    Start From $84.75
 
 

Private Sailing Tour of Bodega Bay

(4.8 of 88 reviews)

This is a unique experience because you get to sail a 33' boat with a licensed captain. You can be involved as much or as little as you want... More

Free Cancellation
Private Tour
Start From $122.50
 
Private Sailing Tour of Bodega Bay Likely to Sell Out

Private Sailing Tour of Bodega Bay

  • North America
  • Superb88 reviews4.8

This is a unique experience because you get to sail a 33' boat with a licensed captain. You can be i....

    Free Cancellation
    Private Tour
    Start From $122.50
 
 

Full-Day Sailing Trip to Mujeres Island from Playa del Carmen

(3.2 of 23 reviews)

The best way to see Isla Mujeres from Riviera Maya! Set sail for tropical adventure with a luxurious catamaran cruise from Cancun to Isla Mujeres. Includes a guided snorkel tour of the reef and time in downtown Isla Mujeres, open ... More

Free Cancellation
Private Tour
Start From $130.00
 
Full-Day Sailing Trip to Mujeres Island from Playa del Carmen Likely to Sell Out

Full-Day Sailing Trip to Mujeres Island from Playa del Carmen

  • North America
  • Good23 reviews3.2

The best way to see Isla Mujeres from Riviera Maya! Set sail for tropical adventure with a luxurious....

    Free Cancellation
    Private Tour
    Start From $130.00
 
 

Deluxe Catamaran Tour to Isla Mujeres, Drinks, Snorkeling, Buffet

(3.5 of 24 reviews)

Get ready to venture into a fantastic experience aboard our catamaran to Isla Mujeres. You will board the catamaran and we will begin our tour together with our guides and entertainers so that you have a pleasant time. You can as... More

Free Cancellation
Private Tour
Start From $38.90
 
Deluxe Catamaran Tour to Isla Mujeres, Drinks, Snorkeling, Buffet Likely to Sell Out

Deluxe Catamaran Tour to Isla Mujeres, Drinks, Snorkeling, Buffet

  • North America
  • Good24 reviews3.5

Get ready to venture into a fantastic experience aboard our catamaran to Isla Mujeres. You will boa....

    Free Cancellation
    Private Tour
    Start From $38.90
 
 

Private Charleston Harbor Catamaran Sail

(5 of 28 reviews)

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing catamaran. Our modern layout provides a panoramic view with large sliding glass doors between the saloon and the rear deck space, with... More

Free Cancellation
Private Tour
Start From $950.00
 
Private Charleston Harbor Catamaran Sail Likely to Sell Out

Private Charleston Harbor Catamaran Sail

  • North America
  • Superb28 reviews5

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing cata....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Luxury Private Yacht Charter in Cabo San Lucas Mexico

(5 of 8 reviews)

You will take a 2-hour tour of the bay of Cabo San Lucas aboard "Reel Tequila" our 31ft boat with a capacity of up to 6 people maximum, remember that the trip is totally private, only your group and the crew (captain and first mat... More

Free Cancellation
Private Tour
Start From $400.00
 
Luxury Private Yacht Charter in Cabo San Lucas Mexico Likely to Sell Out

Luxury Private Yacht Charter in Cabo San Lucas Mexico

  • North America
  • Superb8 reviews5

You will take a 2-hour tour of the bay of Cabo San Lucas aboard "Reel Tequila" our 31ft boat with a ....

    Free Cancellation
    Private Tour
    Start From $400.00
 
 

Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar

(3.7 of 37 reviews)

Admire the peaceful waters of the Caribbean Sea, aboard a classic or luxury catamaran and enjoy a spectacular day sailing to Isla Mujeres on a fun-filled experience where music, drinks and incredible views will never be lacking. ... More

Free Cancellation
Private Tour
Start From $55.00
 
Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar Likely to Sell Out

Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar

  • North America
  • Very Good37 reviews3.7

Admire the peaceful waters of the Caribbean Sea, aboard a classic or luxury catamaran and enjoy a sp....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Golden Gate Bridge Sailing Tour

(4.8 of 52 reviews)

Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail off to the Golden Gate Bridge and enjoy panoramic views of the San Francisco skyline, Sausalito, Angel Island, Tiburon, and Marin... More

Free Cancellation
Private Tour
Start From $129.00
 
Golden Gate Bridge Sailing Tour Likely to Sell Out

Golden Gate Bridge Sailing Tour

  • North America
  • Superb52 reviews4.8

Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Private Catamaran Tour

(5 of 176 reviews)

Our starting point is the iconic Casa China 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 ecosystem. ... More

Free Cancellation
Private Tour
Start From $990.00
 
Private Catamaran Tour Likely to Sell Out

Private Catamaran Tour

  • North America
  • Superb176 reviews5

Our starting point is the iconic Casa China with incredible views of the lagoon from its 360° looko....

    Free Cancellation
    Private Tour
    Start From $990.00
 
 

Ultimate Bay Tours -Private 25 Travelers- Trimaran Experience

(5 of 176 reviews)

Hey there! Just wanted to share this amazing find with you - a private 43 feet Trimaran in Mazatlan that can accommodate up to 25 passengers. It's decked out with a kitchen, bedroom, bathroom, and even water sports gear like kayak... More

Free Cancellation
Private Tour
Start From $1,250.00
 
Ultimate Bay Tours -Private 25 Travelers- Trimaran Experience Likely to Sell Out

Ultimate Bay Tours -Private 25 Travelers- Trimaran Experience

  • North America
  • Superb176 reviews5

Hey there! Just wanted to share this amazing find with you - a private 43 feet Trimaran in Mazatlan ....

    Free Cancellation
    Private Tour
    Start From $1,250.00
 
 

Private Whale Watching Sailing Tour

(5 of 6 reviews)

Amaze yourself appreciating our most awaited visitors of the year, the Humpback Whales! Book this half-day tour on a beautiful and comfortable sailboat while you enjoy the breeze , the sun and the tide while you look for whales, d... More

Free Cancellation
Private Tour
Start From $828.05
 
Private Whale Watching Sailing Tour Likely to Sell Out

Private Whale Watching Sailing Tour

  • North America
  • Superb6 reviews5

Amaze yourself appreciating our most awaited visitors of the year, the Humpback Whales! Book this ha....

    Free Cancellation
    Private Tour
    Start From $828.05
 
 

Waikiki Heritage and Diamond Head Wildlife Sail

(4.7 of 32 reviews)

Set sail along the iconic Waikiki coastline for a laid-back 1.5-hour afternoon on the water. This experience emphasizes relaxation, scenic views of Oʻahu’s south shore, and casual wildlife watching—keep an eye out for dolphin... More

Free Cancellation
Private Tour
Start From $79.95
 
Waikiki Heritage and Diamond Head Wildlife Sail Likely to Sell Out

Waikiki Heritage and Diamond Head Wildlife Sail

  • North America
  • Superb32 reviews4.7

Set sail along the iconic Waikiki coastline for a laid-back 1.5-hour afternoon on the water. This ex....

    Free Cancellation
    Private Tour
    Start From $79.95
 
 

Private Sailing Charter: Up to 24 Passengers

(5 of 1 review)

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a spectacular private sail around the San Francisco Bay. While our boats are coast guard licensed for 34 passengers, we are limiting... More

Free Cancellation
Private Tour
Start From $1,207.50
 
Private Sailing Charter: Up to 24 Passengers Likely to Sell Out

Private Sailing Charter: Up to 24 Passengers

  • North America
  • Superb1 review5

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a ....

    Free Cancellation
    Private Tour
    Start From $1,207.50
 
 

4hrs / 46ft Catamaran Private Charter From Cancun to Isla Mujeres

(5 of 3 reviews)

This catamaran has capacity up to 45 people. We provide a high quality service, nice boat and we take care of customer during the all the booking process, service and follow up after the tour is performed. Customer´s feedback is ... More

Free Cancellation
Private Tour
Start From $1,700.00
 
4hrs / 46ft Catamaran Private Charter From Cancun to Isla Mujeres Likely to Sell Out

4hrs / 46ft Catamaran Private Charter From Cancun to Isla Mujeres

  • North America
  • Superb3 reviews5

This catamaran has capacity up to 45 people. We provide a high quality service, nice boat and we tak....

    Free Cancellation
    Private Tour
    Start From $1,700.00
 
 

Let's Go Sail the York River in Gloucester Point, Virginia

(5 of 144 reviews)

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern conveniences. Or sit back and relax in the cockpit or up on the bow of the boat for greater privacy. Great idea for engagement, bi... More

Free Cancellation
Private Tour
Start From $96.42
 
Let's Go Sail the York River in Gloucester Point, Virginia Likely to Sell Out

Let's Go Sail the York River in Gloucester Point, Virginia

  • North America
  • Superb144 reviews5

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern ....

    Free Cancellation
    Private Tour
    Start From $96.42
 
 

3hr Discover Sailing Adventure

(5 of 10 reviews)

Embark on a thrilling 3-hour introductory keelboat sailing experience designed for beginners eager to explore the basics of sailing. Guided by experienced instructors on our specially designed First 22 yacht, you’ll dive into es... More

Free Cancellation
Private Tour
Start From $201.15
 
3hr Discover Sailing Adventure Likely to Sell Out

3hr Discover Sailing Adventure

  • North America
  • Superb10 reviews5

Embark on a thrilling 3-hour introductory keelboat sailing experience designed for beginners eager t....

    Free Cancellation
    Private Tour
    Start From $201.15
 
 

Los Cabos Seasonal Whale Watch and Snorkel Tour

(4.7 of 21 reviews)

Available December 15th to April 15th. Enjoy an incredible adventure, departing from the beautiful Marina in Cabo San Lucas the boat as sails towards the Santa Maria or Chileno Bay, will ride along the Sea of Cortes, and you will ... More

Free Cancellation
Private Tour
Start From $239.00
 
Los Cabos Seasonal Whale Watch and Snorkel Tour Likely to Sell Out

Los Cabos Seasonal Whale Watch and Snorkel Tour

  • North America
  • Superb21 reviews4.7

Available December 15th to April 15th. Enjoy an incredible adventure, departing from the beautiful M....

    Free Cancellation
    Private Tour
    Start From $239.00
 
 

Private Sailing Charter in Brooklyn

(5 of 9 reviews)

Are you ready to set sail on a one-of-a-kind tour of New York Harbor? We've got an unforgettable adventure waiting for you! Departing from Brooklyn Bridge Park against the breathtaking backdrop of Lower Manhattan, Tantara sails s... More

Free Cancellation
Private Tour
Start From $630.00
 
Private Sailing Charter in Brooklyn Likely to Sell Out

Private Sailing Charter in Brooklyn

  • North America
  • Superb9 reviews5

Are you ready to set sail on a one-of-a-kind tour of New York Harbor? We've got an unforgettable adv....

    Free Cancellation
    Private Tour
    Start From $630.00
 
 

Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound

(5 of 23 reviews)

Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these waters back in 1792. From Seattle’s Shilshole Bay Marina we sail west across Puget Sound toward the magnificent Olympic Mountains. A... More

Free Cancellation
Private Tour
Start From $120.00
 
Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound Likely to Sell Out

Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound

  • North America
  • Superb23 reviews5

Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these wate....

    Free Cancellation
    Private Tour
    Start From $120.00
 
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