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Top 10 Best North America Sailing Trips

Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 10
 

Morning Whale Watch: Lahaina Harbor

(4.9 of 23 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
Start From $100.22
 
Morning Whale Watch: Lahaina Harbor

Morning Whale Watch: Lahaina Harbor

  • North America
  • Superb23 reviews4.9

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

    Free Cancellation
    Start From $100.22
 
 

Half-Day Luxury Sailing in Puerto Morelos with Open Bar

(4.5 of 2 reviews)

Set sail on the tranquil turquoise waters of Puerto Morelos aboard a luxury catamaran for an unforgettable half-day adventure. This experience offers a guided snorkeling session at a vibrant reef in the Mesoamerican Barrier Reef, ... More

Free Cancellation
Start From $149.00
 
Half-Day Luxury Sailing in Puerto Morelos with Open Bar

Half-Day Luxury Sailing in Puerto Morelos with Open Bar

  • North America
  • Exellent2 reviews4.5

Set sail on the tranquil turquoise waters of Puerto Morelos aboard a luxury catamaran for an unforge....

    Free Cancellation
    Start From $149.00
 
 

2-Hour Private Sailing Experience in San Diego Bay

(5 of 168 reviews)

Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing to obtain in today's world. With all the stress life brings we are happy to provide a peacefu... More

Free Cancellation
Private Tour
Start From $625.00
 
2-Hour Private Sailing Experience in San Diego Bay

2-Hour Private Sailing Experience in San Diego Bay

  • North America
  • Superb168 reviews5

Our unique sail displays a peace sign because that is exactly what we share with our customers, peac....

    Free Cancellation
    Private Tour
    Start From $625.00
 
 

Suncoast Sailing's Day Sailing Experience!

(4.9 of 106 reviews)

Join us aboard the iconic schooner, Suncoast Horizon and step aboard our 2 hour sailing excursion. Feel the wind as it glides us through the picturesque waters of Treasure Island and Gulf of Mexico. Come face to face with nature a... More

Free Cancellation
Private Tour
Start From $64.99
 
Suncoast Sailing's Day Sailing Experience!

Suncoast Sailing's Day Sailing Experience!

  • North America
  • Superb106 reviews4.9

Join us aboard the iconic schooner, Suncoast Horizon and step aboard our 2 hour sailing excursion. F....

    Free Cancellation
    Private Tour
    Start From $64.99
 
 

9am Turtle Canyon Snorkel Adventure

(4.9 of 276 reviews)

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

Free Cancellation
Private Tour
Start From $84.77
 
9am Turtle Canyon Snorkel Adventure

9am Turtle Canyon Snorkel Adventure

  • North America
  • Superb276 reviews4.9

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....

    Free Cancellation
    Private Tour
    Start From $84.77
 
 

Best Private Luxury Daytime Boat Tour in New York City - 1 Hour

(4.9 of 39 reviews)

Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time, then climb aboard a luxurious, 28-foot powerboat cruiser and enjoy a relaxing and comfortable journey around lower Manhattan. En... More

Free Cancellation
Private Tour
Start From $350.00
 
Best Private Luxury Daytime Boat Tour in New York City - 1 Hour

Best Private Luxury Daytime Boat Tour in New York City - 1 Hour

  • North America
  • Superb39 reviews4.9

Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time....

    Free Cancellation
    Private Tour
    Start From $350.00
 
 

Small-Group San Diego Afternoon Sailing Excursion

(5 of 532 reviews)

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five friends and fill up the whole boat!). Sit back, relax and enjoy the com... More

Free Cancellation
Private Tour
Start From $116.00
 
Small-Group San Diego Afternoon Sailing Excursion Likely to Sell Out

Small-Group San Diego Afternoon Sailing Excursion

  • North America
  • Superb532 reviews5

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing....

    Free Cancellation
    Private Tour
    Start From $116.00
 
 

Private Customizable Sailing Tour in Cancun

(4.7 of 121 reviews)

Enjoy a private sailing tour for just you and your party aboard a private sailboat which offers the opportunity to visit wonderful places that can only be known by the sea. From a relaxing private sailing tour in the bay of Can... More

Free Cancellation
Private Tour
Start From $549.34
 
Private Customizable Sailing Tour in Cancun Likely to Sell Out

Private Customizable Sailing Tour in Cancun

  • North America
  • Superb121 reviews4.7

Enjoy a private sailing tour for just you and your party aboard a private sailboat which offers th....

    Free Cancellation
    Private Tour
    Start From $549.34
 
 

Luxury Catamaran tour to isla mujeres with transportation from Tulum

(3.5 of 64 reviews)

Excellent service on board Professional crew members Safety measures in all our activities Sanitary prevention protocols for all our guests and staff Once in a lifetime experience Delicious buffet lunch and drinks Beach club (beac... More

Free Cancellation
Private Tour
Start From $110.77
 
Luxury Catamaran tour to isla mujeres with transportation from Tulum Likely to Sell Out

Luxury Catamaran tour to isla mujeres with transportation from Tu....

  • North America
  • Good64 reviews3.5

Excellent service on board Professional crew members Safety measures in all our activities Sanitary ....

    Free Cancellation
    Private Tour
    Start From $110.77
 
 

Tall Ship Silva Sailing Cruise Ft. a Live Musician

(4.2 of 289 reviews)

A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Halifax Harbour. Join us on our comfortable and thoroughly impressive vessel for this relaxing afternoon outing on the water. Your j... More

Free Cancellation
Private Tour
Start From $40.73
 
Tall Ship Silva Sailing Cruise Ft. a Live Musician Likely to Sell Out

Tall Ship Silva Sailing Cruise Ft. a Live Musician

  • North America
  • Exellent289 reviews4.2

A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Ha....

    Free Cancellation
    Private Tour
    Start From $40.73
 
 

Sailing Tour through the Lagoon of the 7 Colors

(4.9 of 1,165 reviews)

Sail with people who share your passion for adventure! You will explore fascinating places along the lagoon of the 7 colors. Our small groups guarantee you excellent attention and service from our crew. Disconnect from the world ... More

Free Cancellation
Private Tour
Start From $37.00
 
Sailing Tour through the Lagoon of the 7 Colors Likely to Sell Out

Sailing Tour through the Lagoon of the 7 Colors

  • North America
  • Superb1,165 reviews4.9

Sail with people who share your passion for adventure! You will explore fascinating places along the....

    Free Cancellation
    Private Tour
    Start From $37.00
 
 

Cozumel Luxury Sailing & Snorkeling with Lunch and Open Bar Onboard

(4.7 of 249 reviews)

• Enjoy the turquoise waters of Cozumel aboard one of our luxury sailing catamarans. • Snorkel and marvel at the wide array of tropical fish and rich marine life that inhabit the colorful reefs of the island. • Paddleboard a... More

Free Cancellation
Private Tour
Start From $139.00
 
Cozumel Luxury Sailing & Snorkeling with Lunch and Open Bar Onboard Likely to Sell Out

Cozumel Luxury Sailing & Snorkeling with Lunch and Open Bar Onboa....

  • North America
  • Superb249 reviews4.7

• Enjoy the turquoise waters of Cozumel aboard one of our luxury sailing catamarans. • Snorkel a....

    Free Cancellation
    Private Tour
    Start From $139.00
 
 

Tulum: Snorkeling and Private Sailing Tour

(4.9 of 166 reviews)

We will enjoy a wonderful catamaran tour, powered only by the wind, we will be able to enjoy a spectacular view of the Tulum ruins from the sea... More

Free Cancellation
Private Tour
Start From $63.96
 
Tulum: Snorkeling and Private Sailing Tour Likely to Sell Out

Tulum: Snorkeling and Private Sailing Tour

  • North America
  • Superb166 reviews4.9

We will enjoy a wonderful catamaran tour, powered only by the wind, we will be able to enjoy a spect....

    Free Cancellation
    Private Tour
    Start From $63.96
 
 

Wrightsville Beach Sunset Cocktail Sail

(5 of 9 reviews)

Relax aboard our 44' catamaran Bella on this evening sail. Enjoy a Caribbean-inspired cocktail while you cruise our local waterways and watch the sunset. Wind permitting, we'll turn off the engines and enjoy the beauty of sailing!... More

Free Cancellation
Private Tour
Start From $150.00
 
Wrightsville Beach Sunset Cocktail Sail Likely to Sell Out

Wrightsville Beach Sunset Cocktail Sail

  • North America
  • Superb9 reviews5

Relax aboard our 44' catamaran Bella on this evening sail. Enjoy a Caribbean-inspired cocktail while....

    Free Cancellation
    Private Tour
    Start From $150.00
 
 

Cabo San Lucas Small-Group Whale Watching Tour: Hear the Whales

(4.9 of 12 reviews)

Your whale watching tour in Cabo San Lucas will become magical with the help of professional-grade hydrophones. If whales are communicating, you may be lucky to get the rare opportunity to hear the whale songs live! Our RABEN (Me... More

Free Cancellation
Private Tour
Start From $99.00
 
Cabo San Lucas Small-Group Whale Watching Tour: Hear the Whales Likely to Sell Out

Cabo San Lucas Small-Group Whale Watching Tour: Hear the Whales

  • North America
  • Superb12 reviews4.9

Your whale watching tour in Cabo San Lucas will become magical with the help of professional-grade h....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Windjammer Classic Sunset Sail from Camden, Maine

(4.9 of 425 reviews)

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. She is a modern windjammer with luxurious accommodations and plent... More

Free Cancellation
Private Tour
Start From $64.95
 
Windjammer Classic Sunset Sail from Camden, Maine Likely to Sell Out

Windjammer Classic Sunset Sail from Camden, Maine

  • North America
  • Superb425 reviews4.9

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....

    Free Cancellation
    Private Tour
    Start From $64.95
 
 

Los Cabos Seasonal Whale Watch and Snorkel Tour

(4.7 of 20 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
  • Superb20 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 Catamaran Sunset Sail in Waikiki

(5 of 10 reviews)

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large ... More

Free Cancellation
Private Tour
Start From $900.00
 
Private Catamaran Sunset Sail in Waikiki Likely to Sell Out

Private Catamaran Sunset Sail in Waikiki

  • North America
  • Superb10 reviews5

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....

    Free Cancellation
    Private Tour
    Start From $900.00
 
 

Private Therapy Sailing Adventure

(4.8 of 42 reviews)

Old Plank Adventures: Sail into a Deep Relaxed State LUXURY THERAPEUTIC SAILING & AQUATIC EXPEDITIONS Experience the enchanting Mediterranean lifestyle along the stunning SoCal Riviera, where the soothing rhythms of the Pacific O... More

Free Cancellation
Private Tour
Start From $400.00
 
Private Therapy Sailing Adventure Likely to Sell Out

Private Therapy Sailing Adventure

  • North America
  • Superb42 reviews4.8

Old Plank Adventures: Sail into a Deep Relaxed State LUXURY THERAPEUTIC SAILING & AQUATIC EXPEDITION....

    Free Cancellation
    Private Tour
    Start From $400.00
 
 

Private sailing tour of Bacalar Lagoon

(5 of 411 reviews)

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper you. During the tour, you can enjoy a delicious fruit cocktail, water and beer. Our certified guides will make this tour an unfo... More

Free Cancellation
Private Tour
Start From $215.00
 
Private sailing tour of Bacalar Lagoon Likely to Sell Out

Private sailing tour of Bacalar Lagoon

  • North America
  • Superb411 reviews5

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper ....

    Free Cancellation
    Private Tour
    Start From $215.00
 
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