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Top 10 Best North America Sailing Trips

Found 641 Sailing Trips activities in North America. Sort by Popularity. - Page 14
 

2 Hour Private Dolphin Day Sail

(4.9 of 312 reviews)

Put your feet up, relax, and learn about the unique Salt Marsh Ecosystem with all of its nature & beauty, and enjoy some of our local history on this day sail! We’ll cut the engine and let the wind do all of the work while you k... More

Free Cancellation
Private Tour
Start From $379.18
 
2 Hour Private Dolphin Day Sail Likely to Sell Out

2 Hour Private Dolphin Day Sail

  • North America
  • Superb312 reviews4.9

Put your feet up, relax, and learn about the unique Salt Marsh Ecosystem with all of its nature & be....

    Free Cancellation
    Private Tour
    Start From $379.18
 
 

Windjammer Classic Day Sail from Camden, Maine

(4.7 of 334 reviews)

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations on a modern windjammer. With wide ... More

Free Cancellation
Private Tour
Start From $59.95
 
Windjammer Classic Day Sail from Camden, Maine Likely to Sell Out

Windjammer Classic Day Sail from Camden, Maine

  • North America
  • Superb334 reviews4.7

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Key West Sunset Snorkel with Unlimited Draft Beer & Wine

(4.7 of 110 reviews)

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More

Free Cancellation
Private Tour
Start From $56.95
 
Key West Sunset Snorkel with Unlimited Draft Beer & Wine Likely to Sell Out

Key West Sunset Snorkel with Unlimited Draft Beer & Wine

  • North America
  • Superb110 reviews4.7

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....

    Free Cancellation
    Private Tour
    Start From $56.95
 
 

Newport Sightseeing Day Sailing Experience on Schooner Adirondack

(4.9 of 23 reviews)

See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schooner Adirondack. You'll pass by many iconic sights, bridges, lighthouses and more during this 1.5-hour experience!... More

Free Cancellation
Private Tour
Start From $45.00
 
Newport Sightseeing Day Sailing Experience on Schooner Adirondack Likely to Sell Out

Newport Sightseeing Day Sailing Experience on Schooner Adirondack

  • North America
  • Superb23 reviews4.9

See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schoone....

    Free Cancellation
    Private Tour
    Start From $45.00
 
 

Paddle at Dawn with visit to Cenotes and Islands

(4.9 of 23 reviews)

Dare to live a new experience! During this activity you will connect with your ecological SELF as you paddle towards sunrise. Enjoy a delicious picnic in a natural environment while you immerse yourself in warm and crystal clear w... More

Free Cancellation
Private Tour
Start From $21.05
 
Paddle at Dawn with visit to Cenotes and Islands Likely to Sell Out

Paddle at Dawn with visit to Cenotes and Islands

  • North America
  • Superb23 reviews4.9

Dare to live a new experience! During this activity you will connect with your ecological SELF as yo....

    Free Cancellation
    Private Tour
    Start From $21.05
 
 

Private Guided Sunset and Dolphin Cruise up to 6 Passengers

(5 of 54 reviews)

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a full restroom, as well as a... More

Free Cancellation
Private Tour
Start From $249.99
 
Private Guided Sunset and Dolphin Cruise up to 6 Passengers Likely to Sell Out

Private Guided Sunset and Dolphin Cruise up to 6 Passengers

  • North America
  • Superb54 reviews5

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....

    Free Cancellation
    Private Tour
    Start From $249.99
 
 

Key West Nighttime Full Moon Sail

(5 of 3 reviews)

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or an evening out with family and friends. Departing in the evening as the moo... More

Free Cancellation
Private Tour
Start From $83.85
 
Key West Nighttime Full Moon Sail Likely to Sell Out

Key West Nighttime Full Moon Sail

  • North America
  • Superb3 reviews5

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1....

    Free Cancellation
    Private Tour
    Start From $83.85
 
 

Snorkeling Adventure in Isla Mujeres

(3.8 of 12 reviews)

Dare to be part of one of the most enigmatic activities in Cancun and Mexico. The underwater museum is a unique activity in the world since there is no such thing anywhere. This activity is cataloged as mandatory for all traveler... More

Free Cancellation
Private Tour
Start From $55.00
 
Snorkeling Adventure in Isla Mujeres Likely to Sell Out

Snorkeling Adventure in Isla Mujeres

  • North America
  • Very Good12 reviews3.8

Dare to be part of one of the most enigmatic activities in Cancun and Mexico. The underwater museum....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Luxury Catamaran Whale Watch

(5 of 11 reviews)

Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback whale. The waters off West Maui have long been the favored vacation spot of these massive marine mammals. The Alii Nui provides max... More

Free Cancellation
Private Tour
Start From $159.00
 
Luxury Catamaran Whale Watch Likely to Sell Out

Luxury Catamaran Whale Watch

  • North America
  • Superb11 reviews5

Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback w....

    Free Cancellation
    Private Tour
    Start From $159.00
 
 

Classic Tall Ship Sightseeing Cruise of Boston Harbor

(4.7 of 454 reviews)

Come out for a day sail adventure in Boston Harbor aboard our classic schooner, the Liberty Star. Get away from the hustle and bustle of the city streets and enjoy some quality time out on the water with unbeatable views of the ci... More

Free Cancellation
Private Tour
Start From $35.00
 
Classic Tall Ship Sightseeing Cruise of Boston Harbor Likely to Sell Out

Classic Tall Ship Sightseeing Cruise of Boston Harbor

  • North America
  • Superb454 reviews4.7

Come out for a day sail adventure in Boston Harbor aboard our classic schooner, the Liberty Star. Ge....

    Free Cancellation
    Private Tour
    Start From $35.00
 
 

52' Yacht Rental in Miami Beach with Experienced Captain

(4.6 of 5 reviews)

Enjoy the day on the water with friends & family in Miami Beach with Dolphin Water Sport. Our +650 reviews on Google with a 4.9 score guarantee our quality. Our Yacht & Captains are certified & licensed by the USCG, giving you a... More

Free Cancellation
Private Tour
Start From $1,650.00
 
52' Yacht Rental in Miami Beach with Experienced Captain Likely to Sell Out

52' Yacht Rental in Miami Beach with Experienced Captain

  • North America
  • Superb5 reviews4.6

Enjoy the day on the water with friends & family in Miami Beach with Dolphin Water Sport. Our +650 ....

    Free Cancellation
    Private Tour
    Start From $1,650.00
 
 

Private Sunset Sail in Key West Florida

(4.6 of 5 reviews)

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch Key West's Famous sunsets. View Dolphins, Turtles, and all kinds of Marine Life. Take the helm, l... More

Free Cancellation
Private Tour
Start From $750.00
 
Private Sunset Sail in Key West Florida Likely to Sell Out

Private Sunset Sail in Key West Florida

  • North America
  • Superb5 reviews4.6

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just ....

    Free Cancellation
    Private Tour
    Start From $750.00
 
 

Private Sunset Sailing with Dolphin and History Tours on Mystique

(5 of 22 reviews)

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor for over 12 years, our sailing yachts are the highest quality and op... More

Free Cancellation
Private Tour
Start From $550.00
 
Private Sunset Sailing with Dolphin and History Tours on Mystique Likely to Sell Out

Private Sunset Sailing with Dolphin and History Tours on Mystique

  • North America
  • Superb22 reviews5

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....

    Free Cancellation
    Private Tour
    Start From $550.00
 
 

South Beach Miami BACHELORETTE Boat Day!

(5 of 1 review)

Enjoy a yacht-day bachelorette trip where everything is already set to go right from the biggest and best marina in SOUTH BEACH... We've found the boats, brought on the food and drinks, and made sure that everything that a good y... More

Free Cancellation
Private Tour
Start From $1,795.00
 
South Beach Miami BACHELORETTE Boat Day! Likely to Sell Out

South Beach Miami BACHELORETTE Boat Day!

  • North America
  • Superb1 review5

Enjoy a yacht-day bachelorette trip where everything is already set to go right from the biggest and....

    Free Cancellation
    Private Tour
    Start From $1,795.00
 
 

Polynesian Canoe Morning Sail

(5 of 16 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Free Cancellation
Private Tour
Start From $200.00
 
Polynesian Canoe Morning Sail Likely to Sell Out

Polynesian Canoe Morning Sail

  • North America
  • Superb16 reviews5

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Free Cancellation
    Private Tour
    Start From $200.00
 
 

3 in 1 Snorkeling, Parasailing, with Meco Ruins Free

(5 of 1 review)

Have a funny and incredible experience full of nature, doing 3 activities at water and land in a tour package! Fly and see the gorgeous views of the Carribean at 260 ft. By the way, you feel free and you liberate adrenaline! ... More

Free Cancellation
Private Tour
Start From $180.00
 
3 in 1 Snorkeling, Parasailing, with Meco Ruins Free Likely to Sell Out

3 in 1 Snorkeling, Parasailing, with Meco Ruins Free

  • North America
  • Superb1 review5

Have a funny and incredible experience full of nature, doing 3 activities at water and land in a tou....

    Free Cancellation
    Private Tour
    Start From $180.00
 
 

Midday Sail with the Whales Ma'alaea

(4.9 of 99 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 $91.89
 
Midday Sail with the Whales Ma'alaea Likely to Sell Out

Midday Sail with the Whales Ma'alaea

  • North America
  • Superb99 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 $91.89
 
 

Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles

(5 of 1 review)

This 8 hour private tour includes a 5 hour custom tour of the island, and a 2.5 hour sail on a sailboat including swimming or snorkeling with turtles. You can pick and choose the stops on the island tour and go at your own pace. ... More

Free Cancellation
Private Tour
Start From $1,100.00
 
Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles Likely to Sell Out

Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles

  • North America
  • Superb1 review5

This 8 hour private tour includes a 5 hour custom tour of the island, and a 2.5 hour sail on a sailb....

    Free Cancellation
    Private Tour
    Start From $1,100.00
 
 

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
 
 

Private Cabo catamaran experience

(4.9 of 312 reviews)

Barta is an extremely fun and comfort 36ft catamaran specifically designed to accommodate large groups of up to 15 passengers. Immerse yourself in the scenic wonders of the bay of Cabo San Lucas as Barta gracefully navigates, ensu... More

Free Cancellation
Private Tour
Start From $1,300.00
 
Private Cabo catamaran experience Likely to Sell Out

Private Cabo catamaran experience

  • North America
  • Superb312 reviews4.9

Barta is an extremely fun and comfort 36ft catamaran specifically designed to accommodate large grou....

    Free Cancellation
    Private Tour
    Start From $1,300.00
 
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