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Top 10 Best North America Sailing Trips

Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 25
 

Key West Private Charter: Sandbar and Snorkeling

(5 of 14 reviews)

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a formal, guided eco-tour, this trip offers a more laid-back vibe, allowing you t... More

Private Tour
Start From $950.00
 
Key West Private Charter: Sandbar and Snorkeling Likely to Sell Out

Key West Private Charter: Sandbar and Snorkeling

  • North America
  • Superb14 reviews5

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who wa....

    Private Tour
    Start From $950.00
 
 

Honolua Snorkel Sail from Lahaina

(4.9 of 61 reviews)

Sail to the storied waters of Honolua Bay, long valued in Hawaiian culture and now protected as a Marine Life Conservation District. Along the way, watch for wild dolphins, then snorkel among Hawaiian green sea turtles in this vib... More

Free Cancellation
Private Tour
Start From $180.92
 
Honolua Snorkel Sail from Lahaina Likely to Sell Out

Honolua Snorkel Sail from Lahaina

  • North America
  • Superb61 reviews4.9

Sail to the storied waters of Honolua Bay, long valued in Hawaiian culture and now protected as a Ma....

    Free Cancellation
    Private Tour
    Start From $180.92
 
 

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

(3.6 of 25 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
  • Very Good25 reviews3.6

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
 
 

Golden Gate Bridge Sailing Tour

(4.8 of 54 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
  • Superb54 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
 
 

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
 
 

Sunset sail Aboard Manakai Catamaran

(5 of 23 reviews)

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a smaller guest capacity and open-deck layout, it offers an intimate, lai... More

Free Cancellation
Private Tour
Start From $49.82
 
Sunset sail Aboard Manakai Catamaran Likely to Sell Out

Sunset sail Aboard Manakai Catamaran

  • North America
  • Superb23 reviews5

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Wood....

    Free Cancellation
    Private Tour
    Start From $49.82
 
 

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
 
 

Private Catamaran Tour

(5 of 191 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
  • Superb191 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
 
 

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
 
 

Ultimate Bay Tours -Private 25 Travelers- Trimaran Experience

(5 of 1 review)

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
  • Superb1 review5

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
 
 

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 $59.00
 
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 $59.00
 
 

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 $824.79
 
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 $824.79
 
 

Morning Whale Watch: Lahaina Harbor

(4.9 of 29 reviews)

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More

Free Cancellation
Private Tour
Start From $100.22
 
Morning Whale Watch: Lahaina Harbor Likely to Sell Out

Morning Whale Watch: Lahaina Harbor

  • North America
  • Superb29 reviews4.9

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....

    Free Cancellation
    Private Tour
    Start From $100.22
 
 

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

(5 of 4 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
  • Superb4 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
 
 

Baltimore Inner Harbor BYOB Sunset Sail on the Unforgettable

(4.7 of 7 reviews)

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of the skyline. Our trips are BYOB so bring your favorite bottle of wine for a special e... More

Free Cancellation
Private Tour
Start From $75.00
 
Baltimore Inner Harbor BYOB Sunset Sail on the Unforgettable Likely to Sell Out

Baltimore Inner Harbor BYOB Sunset Sail on the Unforgettable

  • North America
  • Superb7 reviews4.7

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun s....

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

Baltimore Inner Harbor Sunset Sail on Summer Wind

(4.9 of 58 reviews)

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of the skyline. Bring wine for a special experience on this Inner Harbor sunset sail. S... More

Free Cancellation
Private Tour
Start From $75.00
 
Baltimore Inner Harbor Sunset Sail on Summer Wind Likely to Sell Out

Baltimore Inner Harbor Sunset Sail on Summer Wind

  • North America
  • Superb58 reviews4.9

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun s....

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

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
 
 

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
 
 

Private Boat Snorkeling & Beach: 5 Hours + 1 Free in Vallarta

(5 of 2 reviews)

Sail on a private trip aboard our 26-foot boat. Ideal for up to 8 passengers. We are sure that with us you will know the best part of our beautiful bay of Puerto Vallarta. Do not miss the opportunity we offer you to make this rese... More

Free Cancellation
Private Tour
Start From $1,001.47
 
Private Boat Snorkeling & Beach: 5 Hours + 1 Free in Vallarta Likely to Sell Out

Private Boat Snorkeling & Beach: 5 Hours + 1 Free in Vallarta

  • North America
  • Superb2 reviews5

Sail on a private trip aboard our 26-foot boat. Ideal for up to 8 passengers. We are sure that with ....

    Free Cancellation
    Private Tour
    Start From $1,001.47
 
 

Champagne Dolphin Sail and Reef Snorkel

(4.6 of 10 reviews)

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with only 17 passengers maximum. Avoid the crowds and enjoy sailing, coral reef snorkeling and the ... More

Free Cancellation
Private Tour
Start From $108.91
 
Champagne Dolphin Sail and Reef Snorkel Likely to Sell Out

Champagne Dolphin Sail and Reef Snorkel

  • North America
  • Superb10 reviews4.6

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now l....

    Free Cancellation
    Private Tour
    Start From $108.91
 
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