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Top 10 Best North America Sailing Trips

Found 674 Sailing Trips activities in North America. Sort by Popularity. - Page 18
 

JFarwell Best of Halifax Harbour Tour

(5 of 48 reviews)

This 45' sailing yacht is the perfect venue to learn about the history of Halifax. You are alongside our Captain and Deckhand throughout the sailing experience, and encouraged to ask questions about landmarks and things you see i... More

Free Cancellation
Start From $41.99
 
JFarwell Best of Halifax Harbour Tour Likely to Sell Out

JFarwell Best of Halifax Harbour Tour

  • North America
  • Superb48 reviews5

This 45' sailing yacht is the perfect venue to learn about the history of Halifax. You are alongsid....

    Free Cancellation
    Start From $41.99
 
 

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

(4.6 of 12 reviews)

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and family to see all the iconic waterfront sights of Newport and Narraganset... More

Free Cancellation
Start From $57.24
 
Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport Likely to Sell Out

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

  • North America
  • Superb12 reviews4.6

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard ....

    Free Cancellation
    Start From $57.24
 
 

90 Minute Sailing Tour of Portland

(3.5 of 4 reviews)

Our tour begins with a cruise across the river to the most expensive floating homes on the Willamette. We then usually head down the historic Holgate channel on Portland's own "Jungle Cruise" to the spectacular city riverfront wh... More

Free Cancellation
Start From $99.00
 
90 Minute Sailing Tour of Portland Likely to Sell Out

90 Minute Sailing Tour of Portland

  • North America
  • Good4 reviews3.5

Our tour begins with a cruise across the river to the most expensive floating homes on the Willamet....

    Free Cancellation
    Start From $99.00
 
 

Jungle Tour In Cancun, drive a speedboat through the lagoon with your companion

(4.3 of 3 reviews)

Welcome to the most enigmatic activity in Cancun, the famous jungle tour, this is the best and quick way to know Cancun and all its beauty. Here you will know the Nichupte Lagoon that is a marvelous lagoon in Mexico, here you will... More

Free Cancellation
Start From $45.00
 
Jungle Tour In Cancun, drive a speedboat through the lagoon with your companion Likely to Sell Out

Jungle Tour In Cancun, drive a speedboat through the lagoon with ....

  • North America
  • Exellent3 reviews4.3

Welcome to the most enigmatic activity in Cancun, the famous jungle tour, this is the best and quick....

    Free Cancellation
    Start From $45.00
 
 

Catamaran with Open Bar through the Lagoon of the 7 Colors

(5 of 63 reviews)

Bacalar is the perfect place to live this experience. This wonderful region has the calmest waters in the Caribbean and has the most fascinating tropical landscapes. You will visit the most beautiful places in the lagoon where yo... More

Free Cancellation
Start From $96.00
 
Catamaran with Open Bar through the Lagoon of the 7 Colors Likely to Sell Out

Catamaran with Open Bar through the Lagoon of the 7 Colors

  • North America
  • Superb63 reviews5

Bacalar is the perfect place to live this experience. This wonderful region has the calmest waters i....

    Free Cancellation
    Start From $96.00
 
 

Banderas Bay Sailing Adventures

(5 of 31 reviews)

Join an unforgettable sailing experience led by a captain who has single handily crossed the Pacific 4 times! You’ll explore the breathtaking beauty of Banderas Bay in comfort and style aboard a 40 foot sloop. Private charter lu... More

Free Cancellation
Private Tour
Start From $123.43
 
Banderas Bay Sailing Adventures Likely to Sell Out

Banderas Bay Sailing Adventures

  • North America
  • Superb31 reviews5

Join an unforgettable sailing experience led by a captain who has single handily crossed the Pacific....

    Free Cancellation
    Private Tour
    Start From $123.43
 
 

Isla Mujeres Catamaran Day Trip with Snorkel Open Bar and Buffet

(2 of 1 review)

Discover the Magic of Isla Mujeres on a Catamaran Adventure! Sail across the turquoise Caribbean waters from Cancun to Isla Mujeres on this unforgettable catamaran tour. Perfect for adventure seekers and families alike, this expe... More

Free Cancellation
Private Tour
Start From $79.00
 
Isla Mujeres Catamaran Day Trip with Snorkel Open Bar and Buffet Likely to Sell Out

Isla Mujeres Catamaran Day Trip with Snorkel Open Bar and Buffet

  • North America

Discover the Magic of Isla Mujeres on a Catamaran Adventure! Sail across the turquoise Caribbean wa....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Sunrise in Paddle with Picnic in front of the Bird Sanctuary

(5 of 245 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 $25.71
 
Sunrise in Paddle with Picnic in front of the Bird Sanctuary Likely to Sell Out

Sunrise in Paddle with Picnic in front of the Bird Sanctuary

  • North America
  • Superb245 reviews5

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

    Free Cancellation
    Private Tour
    Start From $25.71
 
 

2.5 hr Sailboat Tour aboard Orion's Child

(5 of 47 reviews)

TripAdvisor SPECIAL MONDAY ONLY Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel. Multiple daily sails that include a quarter day and sunset sa... More

Free Cancellation
Private Tour
Start From $99.00
 
2.5 hr Sailboat Tour aboard Orion's Child Likely to Sell Out

2.5 hr Sailboat Tour aboard Orion's Child

  • North America
  • Superb47 reviews5

TripAdvisor SPECIAL MONDAY ONLY Sail. SEE OUR WEBSITE for other options and availability. Since 2009....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Schooner Appledore Day Sail with Full Bar in Key West

(5 of 43 reviews)

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comf... More

Free Cancellation
Private Tour
Start From $49.00
 
Schooner Appledore Day Sail with Full Bar in Key West Likely to Sell Out

Schooner Appledore Day Sail with Full Bar in Key West

  • North America
  • Superb43 reviews5

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....

    Free Cancellation
    Private Tour
    Start From $49.00
 
 

Sailing Experience on a 50’ sailboat

(5 of 67 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 $106.76
 
Sailing Experience on a 50’ sailboat Likely to Sell Out

Sailing Experience on a 50’ sailboat

  • North America
  • Superb67 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 $106.76
 
 

Halifax Sunset Cruise

(5 of 2 reviews)

Experience golden hour, that magical time of night when the sun makes its way below the horizon, on the Halifax Sunset Cruise aboard our signature ship, the Tall Ship Silva. Purchase wine, beer, cocktails, and other beverages from... More

Free Cancellation
Private Tour
Start From $36.94
 
Halifax Sunset Cruise Likely to Sell Out

Halifax Sunset Cruise

  • North America
  • Superb2 reviews5

Experience golden hour, that magical time of night when the sun makes its way below the horizon, on ....

    Free Cancellation
    Private Tour
    Start From $36.94
 
 

New York Sunset Schooner Cruise on the Hudson River

(4.9 of 198 reviews)

Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known as Schooner Adirondack - inspired by the pilot schooners of... More

Free Cancellation
Private Tour
Start From $99.64
 
New York Sunset Schooner Cruise on the Hudson River Likely to Sell Out

New York Sunset Schooner Cruise on the Hudson River

  • North America
  • Superb198 reviews4.9

Experience a New York City sunset from the water on this evening sightseeing sail past many famous w....

    Free Cancellation
    Private Tour
    Start From $99.64
 
 

Sunset Sail Experience by Catamaran in Waikiki

(5 of 4 reviews)

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu skyline from offshore Waikiki and feel the warmth of the setting Hawaiian sun and tropical ... More

Free Cancellation
Private Tour
Start From $92.31
 
Sunset Sail Experience by Catamaran in Waikiki Likely to Sell Out

Sunset Sail Experience by Catamaran in Waikiki

  • North America
  • Superb4 reviews5

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled ca....

    Free Cancellation
    Private Tour
    Start From $92.31
 
 

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 $57.24
 
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 $57.24
 
 

Whale Watching Amazing Adventure

(4.9 of 23 reviews)

Get ready for the adventure of a lifetime as we make our way out onto the waters surrounding Los Cabos in search of the Cabo’s Whales.” Enjoy listening to the beautiful song of the whales, with the help of our new hydrophones... More

Free Cancellation
Private Tour
Start From $97.00
 
Whale Watching Amazing Adventure Likely to Sell Out

Whale Watching Amazing Adventure

  • North America
  • Superb23 reviews4.9

Get ready for the adventure of a lifetime as we make our way out onto the waters surrounding Los Cab....

    Free Cancellation
    Private Tour
    Start From $97.00
 
 

Waikiki Friday Firework Catamaran Tour

(4.7 of 27 reviews)

The Blue Ocean Waikiki luxury catamaran is the perfect place for guests to enjoy following a breathtaking fireworks just outside the Hilton Hawaiian Village. Every Friday at 6:45pm, you have the opportunity to watch a spectacular ... More

Free Cancellation
Private Tour
Start From $69.99
 
Waikiki Friday Firework Catamaran Tour Likely to Sell Out

Waikiki Friday Firework Catamaran Tour

  • North America
  • Superb27 reviews4.7

The Blue Ocean Waikiki luxury catamaran is the perfect place for guests to enjoy following a breatht....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Speedboat tour and snorkel from Plaza La Isla (shared speedboat)

(5 of 4 reviews)

Enjoy a once-in-a-lifetime adventure on our guided speedboat and snorkel tour, which departs from Plaza la Isla shopping center in Cancun's hotel zone! Best of all, no prior sailing experience is required! Our 13-foot speedboats a... More

Special Offer
Free Cancellation
Private Tour
Start From $56.05
(Saving 5% ) $59.00
 
-5% Speedboat tour and snorkel from Plaza La Isla (shared speedboat) Likely to Sell Out

Speedboat tour and snorkel from Plaza La Isla (shared speedboat)

  • North America
  • Superb4 reviews5

Enjoy a once-in-a-lifetime adventure on our guided speedboat and snorkel tour, which departs from Pl....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $56.05
    (Saving 5% ) $59.00
 
 

Guided Tour of Puerto Morelos Reefs with Snorkeling Experience

(3.5 of 2 reviews)

Welcome to an incredible adventure, if what you like is getting to know new places and being in contact with nature, then this activity is for you. We will take you to know the second largest coral reef in the world, the first one... More

Free Cancellation
Private Tour
Start From $55.00
 
Guided Tour of Puerto Morelos Reefs with Snorkeling Experience Likely to Sell Out

Guided Tour of Puerto Morelos Reefs with Snorkeling Experience

  • North America
  • Good2 reviews3.5

Welcome to an incredible adventure, if what you like is getting to know new places and being in cont....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Romantic Sunset Sailing in Cabo

(3.5 of 2 reviews)

Designed with couples in mind, the tour provides a romantic setting aboard a sailboat, where you can enjoy the gentle breeze of Los Cabos while savoring a glass of wine and a gourmet picnic basket. Unlike other tours, this experie... More

Free Cancellation
Private Tour
Start From $120.00
 
Romantic Sunset Sailing in Cabo Likely to Sell Out

Romantic Sunset Sailing in Cabo

  • North America
  • Good2 reviews3.5

Designed with couples in mind, the tour provides a romantic setting aboard a sailboat, where you can....

    Free Cancellation
    Private Tour
    Start From $120.00
 
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