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Top 10 Best North America Sailing Trips

Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 5
 

Casco Bay Morning Windjammer Sail

(4.9 of 39 reviews)

Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. (NOTE: This is NOT a ... More

Free Cancellation
Start From $61.00
 
Casco Bay Morning Windjammer Sail

Casco Bay Morning Windjammer Sail

  • North America
  • Superb39 reviews4.9

Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the per....

    Free Cancellation
    Start From $61.00
 
 

Snorkel with Manta Rays Guaranteed

(4.8 of 757 reviews)

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

Free Cancellation
Start From $141.03
 
Snorkel with Manta Rays Guaranteed

Snorkel with Manta Rays Guaranteed

  • North America
  • Superb757 reviews4.8

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....

    Free Cancellation
    Start From $141.03
 
 

Paragon Lahaina Sunset Sail

(4.9 of 30 reviews)

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the glassy, miraculous ‘au’au Channel is like floating inside an infinite ... More

Free Cancellation
Start From $102.00
 
Paragon Lahaina Sunset Sail

Paragon Lahaina Sunset Sail

  • North America
  • Superb30 reviews4.9

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from L....

    Free Cancellation
    Start From $102.00
 
 

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

(4.6 of 761 reviews)

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More

Free Cancellation
Start From $89.00
 
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

  • North America
  • Superb761 reviews4.6

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....

    Free Cancellation
    Start From $89.00
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 576 reviews)

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters a... More

Free Cancellation
Start From $178.72
 
Deluxe Sail & Snorkel to the Captain Cook Monument

Deluxe Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb576 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....

    Free Cancellation
    Start From $178.72
 
 

New York City Sunset Sail to the Statue of Liberty

(4.8 of 75 reviews)

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic sailboat is 105-feet in length and has about 3600 square feet of sail ... More

Free Cancellation
Start From $90.12
 
New York City Sunset Sail to the Statue of Liberty

New York City Sunset Sail to the Statue of Liberty

  • North America
  • Superb75 reviews4.8

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of B....

    Free Cancellation
    Start From $90.12
 
 

2-Hour Private Sailing Experience in San Diego Bay

(5 of 179 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 $675.00
 
2-Hour Private Sailing Experience in San Diego Bay

2-Hour Private Sailing Experience in San Diego Bay

  • North America
  • Superb179 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 $675.00
 
 

Key West's Favorite Afternoon Dolphin Sail

(4.6 of 214 reviews)

Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! Enjoy sailing aboard a 60' catamaran to the dolphin playground to view wild dolphins play and frolic in their natural habitat. Atla... More

Free Cancellation
Private Tour
Start From $59.00
 
Key West's Favorite Afternoon Dolphin Sail

Key West's Favorite Afternoon Dolphin Sail

  • North America
  • Superb214 reviews4.6

Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....

    Free Cancellation
    Private Tour
    Start From $59.00
 
 

Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

(4.9 of 31 reviews)

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that... More

Free Cancellation
Private Tour
Start From $203.16
 
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

  • North America
  • Superb31 reviews4.9

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....

    Free Cancellation
    Private Tour
    Start From $203.16
 
 

Half-Day Deluxe Molokini Snorkel Excursion in Maui

(4.9 of 130 reviews)

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical fish and coral reefs. Your adventure continues with a second snorkel... More

Free Cancellation
Private Tour
Start From $249.00
 
Half-Day Deluxe Molokini Snorkel Excursion in Maui

Half-Day Deluxe Molokini Snorkel Excursion in Maui

  • North America
  • Superb130 reviews4.9

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....

    Free Cancellation
    Private Tour
    Start From $249.00
 
 

El Cielo Snorkel by Private Boat

(4.8 of 370 reviews)

- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and coral formations - Stop over at a secluded pristine white sandy beach away from the crowds - Taste a delicious fish ceviche and co... More

Free Cancellation
Private Tour
Start From $499.99
 
El Cielo Snorkel by Private Boat

El Cielo Snorkel by Private Boat

  • North America
  • Superb370 reviews4.8

- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and co....

    Free Cancellation
    Private Tour
    Start From $499.99
 
 

Sunset Sail in Key West with Beverages Included

(4.9 of 983 reviews)

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the... More

Free Cancellation
Private Tour
Start From $79.00
 
Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

  • North America
  • Superb983 reviews4.9

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

(4.8 of 2,408 reviews)

Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This romantic sunset cruise on Cabo San Lucas Bay includes unlimited drinks from an open bar, accompanied by a delightful menu of small b... More

Free Cancellation
Private Tour
Start From $82.00
 
Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

  • North America
  • Superb2,408 reviews4.8

Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This ro....

    Free Cancellation
    Private Tour
    Start From $82.00
 
 

Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

(4.5 of 24 reviews)

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, socialize with friends and family and take in the spectacular Maui sunset.... More

Free Cancellation
Private Tour
Start From $59.95
 
Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

  • North America
  • Exellent24 reviews4.5

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, ....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

(4.8 of 317 reviews)

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Free Cancellation
Private Tour
Start From $72.96
 
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

  • North America
  • Superb317 reviews4.8

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....

    Free Cancellation
    Private Tour
    Start From $72.96
 
 

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

(4.9 of 729 reviews)

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk like a pirate then climb aboard the Black Sparrow and set sail in search of treasure! But wait it's no... More

Free Cancellation
Private Tour
Start From $47.99
 
Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

  • North America
  • Superb729 reviews4.9

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos.....

    Free Cancellation
    Private Tour
    Start From $47.99
 
 

Private Luxury Yacht Charters, BYOB & Dolphins

(5 of 424 reviews)

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the water on one of our sailboats. We offer hourly, daily, or customized tours according to you... More

Free Cancellation
Private Tour
Start From $525.00
 
Private Luxury Yacht Charters, BYOB & Dolphins

Private Luxury Yacht Charters, BYOB & Dolphins

  • North America
  • Superb424 reviews5

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the....

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

(4.9 of 358 reviews)

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with Captain Phil, a USCG-licensed captain with 55 years of sailing experience. ... More

Free Cancellation
Private Tour
Start From $125.00
 
Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

  • North America
  • Superb358 reviews4.9

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San ....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Vancouver Sailing Experience on a 50 Foot Sailboat

(5 of 112 reviews)

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for 20 of those, have extensive sailing and local knowledge, 12 years experience volunteering... More

Free Cancellation
Private Tour
Start From $116.02
 
Vancouver Sailing Experience on a 50 Foot Sailboat

Vancouver Sailing Experience on a 50 Foot Sailboat

  • North America
  • Superb112 reviews5

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over ....

    Free Cancellation
    Private Tour
    Start From $116.02
 
 

2-Hour Sunset Sail on the San Francisco Bay

(4.7 of 424 reviews)

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous traditional vessel to take in the sights at the most bewitching time of d... More

Free Cancellation
Private Tour
Start From $129.00
 
2-Hour Sunset Sail on the San Francisco Bay

2-Hour Sunset Sail on the San Francisco Bay

  • North America
  • Superb424 reviews4.7

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....

    Free Cancellation
    Private Tour
    Start From $129.00
 
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