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Top 10 Best North America Sailing Trips

Found 770 Sailing Trips activities in North America. Sort by Popularity. - Page 4
 

Sunset Sail Along the San Diego Skyline

(4.9 of 627 reviews)

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water.  Our San Diego Bay Sunset Sailing Cruises provide an up-close and personal view o... More

Free Cancellation
Start From $99.00
 
Sunset Sail Along the San Diego Skyline Likely to Sell Out

Sunset Sail Along the San Diego Skyline

  • North America
  • Superb627 reviews4.9

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....

    Free Cancellation
    Start From $99.00
 
 

Day Sails and Sunset tours on Schooner Surprise in Camden Maine

(4.9 of 91 reviews)

Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at most and have cushioned seating on board for all. Experienced crew will point out wild life, tell you history of our area and show... More

Free Cancellation
Start From $73.00
 
Day Sails and Sunset tours on Schooner Surprise in Camden Maine Likely to Sell Out

Day Sails and Sunset tours on Schooner Surprise in Camden Maine

  • North America
  • Superb91 reviews4.9

Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at ....

    Free Cancellation
    Start From $73.00
 
 

Half-Day Luxury Sailing Experience in Tulum with Open Bar

(4.2 of 256 reviews)

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so that makes the experience better. The snorkeling is amazing, as you will see much colorful fish, st... More

Free Cancellation
Start From $149.00
 
Half-Day Luxury Sailing Experience in Tulum with Open Bar Likely to Sell Out

Half-Day Luxury Sailing Experience in Tulum with Open Bar

  • North America
  • Exellent256 reviews4.2

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....

    Free Cancellation
    Start From $149.00
 
 

Day's End Cocktail Sunset Sail

(4.7 of 84 reviews)

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. This isn’t a dinner cruise, it’s happy hour reimagined (a true ‘pau hana’ at sea) with handcrafted drin... More

Free Cancellation
Start From $159.00
 
Day's End Cocktail Sunset Sail Likely to Sell Out

Day's End Cocktail Sunset Sail

  • North America
  • Superb84 reviews4.7

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....

    Free Cancellation
    Start From $159.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 733 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
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
  • Superb733 reviews4.9

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

    Free Cancellation
    Start From $136.19
 
 

Sunset Sail in Key West with Beverages Included

(4.9 of 954 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 Likely to Sell Out

Sunset Sail in Key West with Beverages Included

  • North America
  • Superb954 reviews4.9

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

    Free Cancellation
    Start From $79.00
 
 

Deluxe Sunset & Day Sail Small Group

(5 of 291 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
  • Superb291 reviews5

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

    Free Cancellation
    Start From $119.00
 
 

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

(4.4 of 381 reviews)

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant sailing experience. Guests board a spacious Fury Catamaran, part of the largest luxury fleet in the Florida Keys, and sail to North Ame... More

Free Cancellation
Start From $59.95
 
Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail Likely to Sell Out

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

  • North America
  • Exellent381 reviews4.4

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....

    Free Cancellation
    Start From $59.95
 
 

Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

(4.5 of 302 reviews)

Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quality, comfort, and performance. Live the yachting lifestyle, walk barefoot on the deck, feel the sun and breeze on your face, dance ... More

Free Cancellation
Start From $199.00
 
Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef Likely to Sell Out

Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

  • North America
  • Exellent302 reviews4.5

Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quali....

    Free Cancellation
    Start From $199.00
 
 

Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

(5 of 39 reviews)

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based on weather, tides, and ocean conditions. • Explore Lana... More

Free Cancellation
Start From $216.22
 
Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar Likely to Sell Out

Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

  • North America
  • Superb39 reviews5

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where ....

    Free Cancellation
    Start From $216.22
 
 

Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

(4.8 of 2,366 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
Start From $82.00
 
Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar Likely to Sell Out

Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

  • North America
  • Superb2,366 reviews4.8

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

    Free Cancellation
    Start From $82.00
 
 

Monterey Bay Whale Watching

(4.6 of 330 reviews)

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey Bay Canyon, one of the largest underwater canyons in the wor... More

Free Cancellation
Start From $69.95
 
Monterey Bay Whale Watching Likely to Sell Out

Monterey Bay Whale Watching

  • North America
  • Superb330 reviews4.6

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watchi....

    Free Cancellation
    Start From $69.95
 
 

Waikiki Sunset Cruise from Oahu

(4.8 of 61 reviews)

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point to observe marine life such as dolphins, whales, sea... More

Free Cancellation
Start From $45.00
 
Waikiki Sunset Cruise from Oahu Likely to Sell Out

Waikiki Sunset Cruise from Oahu

  • North America
  • Superb61 reviews4.8

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks an....

    Free Cancellation
    Start From $45.00
 
 

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

(4.6 of 26 reviews)

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the island like never before as you set sail from the only pier in W... More

Free Cancellation
Start From $119.95
 
Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village Likely to Sell Out

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

  • North America
  • Superb26 reviews4.6

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-bui....

    Free Cancellation
    Start From $119.95
 
 

Key West Dolphin and Snorkel Experience

(4.4 of 356 reviews)

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key West Sunset all in one trip.... More

Free Cancellation
Start From $69.95
 
Key West Dolphin and Snorkel Experience Likely to Sell Out

Key West Dolphin and Snorkel Experience

  • North America
  • Exellent356 reviews4.4

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....

    Free Cancellation
    Start From $69.95
 
 

Newport Sunset Sail on Classic Sailboat

(4.8 of 44 reviews)

Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailboat and see all of Newport's iconic sights from the water including histor... More

Free Cancellation
Start From $67.84
 
Newport Sunset Sail on Classic Sailboat Likely to Sell Out

Newport Sunset Sail on Classic Sailboat

  • North America
  • Superb44 reviews4.8

Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a ....

    Free Cancellation
    Start From $67.84
 
 

Newport Sightseeing Day Sailing Experience on Schooner Adirondack

(4.9 of 78 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
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
  • Superb78 reviews4.9

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

    Free Cancellation
    Start From $57.24
 
 

Half-Day Deluxe Molokini Snorkel Excursion in Maui

(4.9 of 119 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
Start From $289.00
 
Half-Day Deluxe Molokini Snorkel Excursion in Maui Likely to Sell Out

Half-Day Deluxe Molokini Snorkel Excursion in Maui

  • North America
  • Superb119 reviews4.9

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

    Free Cancellation
    Start From $289.00
 
 

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

(4.6 of 419 reviews)

If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise on a classic Boston tall ship! We depart Fan Pier Marina and raise the sails, then it’s time to just chill out and relax. Get a... More

Free Cancellation
Start From $81.36
 
Sunset Sailing Cruise on a Tall Ship in Boston Harbor Likely to Sell Out

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

  • North America
  • Superb419 reviews4.6

If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise....

    Free Cancellation
    Start From $81.36
 
 

Sunset Catamaran Cruise in Ft. Lauderdale

(4.8 of 701 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
Start From $129.00
 
Sunset Catamaran Cruise in Ft. Lauderdale Likely to Sell Out

Sunset Catamaran Cruise in Ft. Lauderdale

  • North America
  • Superb701 reviews4.8

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

    Free Cancellation
    Start From $129.00
 
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