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Top 10 Best North America Sailing Trips

Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 22
 

1 Hour Private Charter in New York Harbor for up to 6 people

(4.9 of 52 reviews)

This is a private tour which means it is just you and your party on board. You will be sailing on our beautiful classic sailboat named Tara. Tara is a classic sailboat and one of a kind in NYC. You will sail past Elis Island and t... More

Free Cancellation
Private Tour
Start From $375.00
 
1 Hour Private Charter in New York Harbor for up to 6 people Likely to Sell Out

1 Hour Private Charter in New York Harbor for up to 6 people

  • North America
  • Superb52 reviews4.9

This is a private tour which means it is just you and your party on board. You will be sailing on ou....

    Free Cancellation
    Private Tour
    Start From $375.00
 
 

Hidden Beach - Marietas Islands

(4.4 of 44 reviews)

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

Free Cancellation
Private Tour
Start From $205.00
 
Hidden Beach - Marietas Islands Likely to Sell Out

Hidden Beach - Marietas Islands

  • North America
  • Exellent44 reviews4.4

Spend the day exploring and enjoying the marine life of the Marietas Islands on this 5-hour excursio....

    Free Cancellation
    Private Tour
    Start From $205.00
 
 

Monterey Private 3 - 4 Hour Whale Watching Cruise

(5 of 2 reviews)

Enjoy a 3 - 4 hour sailing cruise on the Monterey Bay. This Marine Mammal and Wildlife Safari is a private guided tour and can accommodate up to 6 people. Whale sightings are NOT guaranteed. However, this tour is designed to give... More

Free Cancellation
Private Tour
Start From $950.00
 
Monterey Private 3 - 4 Hour Whale Watching Cruise Likely to Sell Out

Monterey Private 3 - 4 Hour Whale Watching Cruise

  • North America
  • Superb2 reviews5

Enjoy a 3 - 4 hour sailing cruise on the Monterey Bay. This Marine Mammal and Wildlife Safari is a p....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Deluxe private Sunset & Day Sail

(5 of 2 reviews)

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic landmarks, and into the heart of coastal paradise. Feel the wind in your... More

Special Offer
Free Cancellation
Private Tour
Start From $571.20
(Saving 20% ) $714.00
 
-20% Deluxe private Sunset & Day Sail Likely to Sell Out

Deluxe private Sunset & Day Sail

  • North America
  • Superb2 reviews5

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $571.20
    (Saving 20% ) $714.00
 
 

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 Likely to Sell Out

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
 
 

Private Oahu Sunset Charter with Tasting and Drinks

(5 of 49 reviews)

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people while enjoying the West Oahu Sunset on this 2.5-hour experience. There’s more than enoug... More

Free Cancellation
Private Tour
Start From $1,413.61
 
Private Oahu Sunset Charter with Tasting and Drinks Likely to Sell Out

Private Oahu Sunset Charter with Tasting and Drinks

  • North America
  • Superb49 reviews5

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world....

    Free Cancellation
    Private Tour
    Start From $1,413.61
 
 

Private Sailing Tour of Bodega Bay

(4.8 of 86 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
  • Superb86 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
 
 

Private Catamaran Tour

(5 of 173 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
  • Superb173 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
 
 

2-Hour Morning Sail in San Diego

(4.9 of 27 reviews)

Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma, San Diego Bay and the downtown waterfront. This two-hour adventure on a Catalina sailboat is limited to a maximum of six (6) gues... More

Free Cancellation
Private Tour
Start From $95.00
 
2-Hour Morning Sail in San Diego Likely to Sell Out

2-Hour Morning Sail in San Diego

  • North America
  • Superb27 reviews4.9

Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma,....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

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
 
 

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
 
 

Okanagan Lake Sailing Tour from Penticton & Naramata BC

(5 of 48 reviews)

Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht into the sunny waters of Okanagan Lake. We provide hands on instruction and lots of opportunities to learn or just relax. And it is ... More

Free Cancellation
Private Tour
Start From $187.04
 
Okanagan Lake Sailing Tour from Penticton & Naramata BC Likely to Sell Out

Okanagan Lake Sailing Tour from Penticton & Naramata BC

  • North America
  • Superb48 reviews5

Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht int....

    Free Cancellation
    Private Tour
    Start From $187.04
 
 

Private Catamaran from Cancun to Isla Mujeres | For up to 40 pp

(4.3 of 69 reviews)

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

Free Cancellation
Private Tour
Start From $2,231.00
 
Private Catamaran from Cancun to Isla Mujeres | For up to 40 pp Likely to Sell Out

Private Catamaran from Cancun to Isla Mujeres | For up to 40 pp

  • North America
  • Exellent69 reviews4.3

Enjoy a day sailing through the Caribbean Sea aboard on a 46 ft Catamaran. Decide if you want to go....

    Free Cancellation
    Private Tour
    Start From $2,231.00
 
 

Private 90-Minute Harbor Sailing Charter in Key West

(4.9 of 18 reviews)

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida Keys and view the city from the water in peace and tranquility. You may even get to see some fri... More

Free Cancellation
Private Tour
Start From $395.00
 
Private 90-Minute Harbor Sailing Charter in Key West Likely to Sell Out

Private 90-Minute Harbor Sailing Charter in Key West

  • North America
  • Superb18 reviews4.9

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-mi....

    Free Cancellation
    Private Tour
    Start From $395.00
 
 

Sailing Snorkel Adventure

(4.5 of 6 reviews)

Interactive Sailing Adventure, Snorkeling, Surf Up Paddle, Premium Bar and Incredible views. This Sailing Boat Adventure is unbeatable Value. ... More

Free Cancellation
Private Tour
Start From $149.00
 
Sailing Snorkel Adventure Likely to Sell Out

Sailing Snorkel Adventure

  • North America
  • Exellent6 reviews4.5

Interactive Sailing Adventure, Snorkeling, Surf Up Paddle, Premium Bar and Incredible views. This Sa....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

BYOB Friday Night Fireworks Cruise

(4.3 of 6 reviews)

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights and be in awe with this unobstructed view of fireworks from the water! With plenty of... More

Free Cancellation
Private Tour
Start From $138.95
 
BYOB Friday Night Fireworks Cruise Likely to Sell Out

BYOB Friday Night Fireworks Cruise

  • North America
  • Exellent6 reviews4.3

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....

    Free Cancellation
    Private Tour
    Start From $138.95
 
 

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
 
 

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

(5 of 141 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
  • Superb141 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
 
 

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
 
 

3hr Discover Sailing Adventure

(5 of 9 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 $201.26
 
3hr Discover Sailing Adventure Likely to Sell Out

3hr Discover Sailing Adventure

  • North America
  • Superb9 reviews5

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

    Free Cancellation
    Private Tour
    Start From $201.26
 
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