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Top 10 Best North America Sailing Trips

Found 693 Sailing Trips activities in North America. Sort by Popularity. - Page 2
 

St. Augustine Live Music Sunset Sail with Drinks Included

(4.8 of 170 reviews)

Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sail! Indulge in complimentary beer, wine, soda, water, margaritas, champagne, and a snack, while enjoying live performances by some ... More

Free Cancellation
Start From $69.17
 
St. Augustine Live Music Sunset Sail with Drinks Included

St. Augustine Live Music Sunset Sail with Drinks Included

  • North America
  • Superb170 reviews4.8

Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sai....

    Free Cancellation
    Start From $69.17
 
 
-12% Seattle Sunset Sail BYOB

Seattle Sunset Sail BYOB

(4.9 of 105 reviews)

Our Sunset Sail is one of the most relaxing and affordable activities in Downtown Seattle. The Sunset Sail is powered by the wind, so it is extremally Eco-Friendly. We are one of the only cruises in the area that allow you to brin... More

Special Offer
Free Cancellation
Start From $60.35
(Saving 12% ) $68.42
 
-12% Seattle Sunset Sail BYOB

Seattle Sunset Sail BYOB

  • North America
  • Superb105 reviews4.9

Our Sunset Sail is one of the most relaxing and affordable activities in Downtown Seattle. The Sunse....

    Special Offer
    Free Cancellation
    Start From $60.35
    (Saving 12% ) $68.42
 
 

Key West Snorkeling with Breakfast and Unlimited Mimosas

(4.5 of 524 reviews)

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light Breakfast and sail to the Key West living reef where you will see coral and tropical fish. All snorkeling... More

Free Cancellation
Start From $52.95
 
Key West Snorkeling with Breakfast and Unlimited Mimosas

Key West Snorkeling with Breakfast and Unlimited Mimosas

  • North America
  • Exellent524 reviews4.5

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....

    Free Cancellation
    Start From $52.95
 
 

1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

(4 of 402 reviews)

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises.... More

Free Cancellation
Start From $70.00
 
1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

  • North America
  • Very Good402 reviews4

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....

    Free Cancellation
    Start From $70.00
 
 

Sunset Sail in Key West with Beverages Included

(4.9 of 825 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
Start From $79.00
 
Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

  • North America
  • Superb825 reviews4.9

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

    Free Cancellation
    Start From $79.00
 
 

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

(4.3 of 1,339 reviews)

Award Winning Cozumel Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire the Spectacular marine life on this awarded Cozumel Snorkeling trip. Enjoy Cozumel's top attractions and most visited reefs in the C... More

Free Cancellation
Start From $65.00
 
Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs Likely to Sell Out

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

  • North America
  • Exellent1,339 reviews4.3

Award Winning Cozumel Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire th....

    Free Cancellation
    Start From $65.00
 
 

Day's End Cocktail Sunset Sail

(4.8 of 26 reviews)

Bring the whole family along for this upscale evening of outstanding food and beverages. We set the sails and chase the sun as it sets into the distant horizon of the azure water of the South Pacific. This casual dining experience... More

Free Cancellation
Start From $149.00
 
Day's End Cocktail Sunset Sail Likely to Sell Out

Day's End Cocktail Sunset Sail

  • North America
  • Superb26 reviews4.8

Bring the whole family along for this upscale evening of outstanding food and beverages. We set the ....

    Free Cancellation
    Start From $149.00
 
 

Deluxe Sunset & Day Sail Small Group

(5 of 145 reviews)

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as the sky transforms into a masterpiece of color. Keep an eye out for playfu... More

Free Cancellation
Start From $119.00
 
Deluxe Sunset & Day Sail Small Group Likely to Sell Out

Deluxe Sunset & Day Sail Small Group

  • North America
  • Superb145 reviews5

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect....

    Free Cancellation
    Start From $119.00
 
 

Private Catamaran Escape for 2–6 Guests – Celebrate Your Way”

(4.9 of 302 reviews)

Set sail on a one-of-a-kind ocean escape designed for small, meaningful moments. Whether you’re celebrating a bachelorette, a birthday, or simply enjoying time with your favorite people, this catamaran getaway for up to six gues... More

Free Cancellation
Private Tour
Start From $595.00
 
Private Catamaran Escape for 2–6 Guests – Celebrate Your Way” Likely to Sell Out

Private Catamaran Escape for 2–6 Guests – Celebrate Your Way....

  • North America
  • Superb302 reviews4.9

Set sail on a one-of-a-kind ocean escape designed for small, meaningful moments. Whether you’re ce....

    Free Cancellation
    Private Tour
    Start From $595.00
 
 

2-Hour Seattle Sailing Harbor Tour

(4.7 of 391 reviews)

Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing tour is family-friendly and is an excellent way to see the Seattle skyline, the beauty of the Puget Sound, even mountain views! We ... More

Free Cancellation
Private Tour
Start From $49.30
 
2-Hour Seattle Sailing Harbor Tour Likely to Sell Out

2-Hour Seattle Sailing Harbor Tour

  • North America
  • Superb391 reviews4.7

Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing t....

    Free Cancellation
    Private Tour
    Start From $49.30
 
 

Turtles & Tacos Luxury Catamaran Snorkel

(4.8 of 32 reviews)

As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are eager to guide you on an unforgettable journey. The vessel is equipped with all the amenities you need for a comfortable and enjoy... More

Free Cancellation
Private Tour
Start From $169.00
 
Turtles & Tacos Luxury Catamaran Snorkel Likely to Sell Out

Turtles & Tacos Luxury Catamaran Snorkel

  • North America
  • Superb32 reviews4.8

As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are ....

    Free Cancellation
    Private Tour
    Start From $169.00
 
 

Sunset Catamaran Cruise in Ft. Lauderdale

(4.8 of 655 reviews)

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach as the sun slips slowly behind the lights of the city. This evening cruise calls for sun ... More

Free Cancellation
Private Tour
Start From $99.00
 
Sunset Catamaran Cruise in Ft. Lauderdale Likely to Sell Out

Sunset Catamaran Cruise in Ft. Lauderdale

  • North America
  • Superb655 reviews4.8

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 680 reviews)

A three hour tour you won't want to miss! 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 a... More

Free Cancellation
Private Tour
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb680 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....

    Free Cancellation
    Private Tour
    Start From $136.19
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 476 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
Private Tour
Start From $177.73
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb476 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $177.73
 
 

Classic Tall Ship Sightseeing Cruise of Boston Harbor

(4.7 of 473 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
  • Superb473 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
 
 

Sightseeing Day Sail around Boston Harbor

(4.7 of 392 reviews)

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail past the seaport district, Castle... More

Free Cancellation
Private Tour
Start From $66.54
 
Sightseeing Day Sail around Boston Harbor Likely to Sell Out

Sightseeing Day Sail around Boston Harbor

  • North America
  • Superb392 reviews4.7

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner....

    Free Cancellation
    Private Tour
    Start From $66.54
 
 

Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club

(4.7 of 110 reviews)

Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among vibrant tropical fish, then relax on Playa Norte, one of Mexico's finest beaches. Departing from the pier, begin with a 30-minut... More

Free Cancellation
Private Tour
Start From $69.00
 
Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club Likely to Sell Out

Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club

  • North America
  • Superb110 reviews4.7

Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among ....

    Free Cancellation
    Private Tour
    Start From $69.00
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 793 reviews)

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More

Free Cancellation
Private Tour
Start From $202.59
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • North America
  • Superb793 reviews4.7

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....

    Free Cancellation
    Private Tour
    Start From $202.59
 
 

Kona-Kohala Coast Sunset Sail by Catamaran

(4.7 of 349 reviews)

Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamaran. Catch the moment the sun slips below the horizon. You may even see the green flash. Board from Anaehoomalu Bay (A-Bay) to sail... More

Free Cancellation
Private Tour
Start From $152.55
 
Kona-Kohala Coast Sunset Sail by Catamaran Likely to Sell Out

Kona-Kohala Coast Sunset Sail by Catamaran

  • North America
  • Superb349 reviews4.7

Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamar....

    Free Cancellation
    Private Tour
    Start From $152.55
 
 

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor

(4.7 of 143 reviews)

Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your loved ones to experience a beautiful Snorkeling, Sailing Cruise, and Whale Watching (Dec-Apr) on our Small Charming Hawaiian Catamara... More

Free Cancellation
Private Tour
Start From $139.00
 
Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor Likely to Sell Out

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harb....

  • North America
  • Superb143 reviews4.7

Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your lov....

    Free Cancellation
    Private Tour
    Start From $139.00
 
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