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Top 10 Best North America Sailing Trips

Found 701 Sailing Trips activities in North America. Sort by Popularity. - Page 3
 

Key West's Favorite Afternoon Dolphin Sail

(4.7 of 72 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
Start From $59.00
 
Key West's Favorite Afternoon Dolphin Sail Likely to Sell Out

Key West's Favorite Afternoon Dolphin Sail

  • North America
  • Superb72 reviews4.7

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

    Free Cancellation
    Start From $59.00
 
 

Sunset Sail Along the San Diego Skyline

(4.9 of 565 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 $115.00
 
Sunset Sail Along the San Diego Skyline Likely to Sell Out

Sunset Sail Along the San Diego Skyline

  • North America
  • Superb565 reviews4.9

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

    Free Cancellation
    Start From $115.00
 
 

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

(4.8 of 65 reviews)

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall. Now operating from Ma'alaea Harbor, we invite you to join our cap... More

Free Cancellation
Start From $119.00
 
Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor Likely to Sell Out

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

  • North America
  • Superb65 reviews4.8

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....

    Free Cancellation
    Start From $119.00
 
 

Sunset Catamaran Cruise in Ft. Lauderdale

(4.8 of 672 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 $99.00
 
Sunset Catamaran Cruise in Ft. Lauderdale Likely to Sell Out

Sunset Catamaran Cruise in Ft. Lauderdale

  • North America
  • Superb672 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 $99.00
 
 

Panama City Beach Sunset Catamaran Sail on The Privateer

(4.8 of 653 reviews)

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer, our 78-passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mex... More

Free Cancellation
Start From $45.00
 
Panama City Beach Sunset Catamaran Sail on The Privateer Likely to Sell Out

Panama City Beach Sunset Catamaran Sail on The Privateer

  • North America
  • Superb653 reviews4.8

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....

    Free Cancellation
    Start From $45.00
 
 

Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club

(4.7 of 123 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
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
  • Superb123 reviews4.7

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

    Free Cancellation
    Start From $69.00
 
 

Cabo San Lucas Sunset Sailing Shared Cruise

(4.9 of 732 reviews)

Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated at night, and see the wonderful sunset contrasting with Cabo San Lucas amazing waters. This is a family-friendly tour and includes... More

Free Cancellation
Start From $105.00
 
Cabo San Lucas Sunset Sailing Shared Cruise Likely to Sell Out

Cabo San Lucas Sunset Sailing Shared Cruise

  • North America
  • Superb732 reviews4.9

Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated ....

    Free Cancellation
    Start From $105.00
 
 

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

(4.9 of 776 reviews)

Explore the sparkling turquoise waters of the Sea of Cortez on this sightseeing snorkel adventure of Los Cabos’ Land’s End Arch! First, you’ll enjoy a beautiful sightseeing stop at Pelican’s Rock where you’ll have a cha... More

Free Cancellation
Start From $105.00
 
Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas Likely to Sell Out

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

  • North America
  • Superb776 reviews4.9

Explore the sparkling turquoise waters of the Sea of Cortez on this sightseeing snorkel adventure of....

    Free Cancellation
    Start From $105.00
 
 

Waikoloa Signature Catamaran Sunset Sail

(4.7 of 351 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
Start From $149.00
 
Waikoloa Signature Catamaran Sunset Sail Likely to Sell Out

Waikoloa Signature Catamaran Sunset Sail

  • North America
  • Superb351 reviews4.7

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

    Free Cancellation
    Start From $149.00
 
 

Sunset Windjammer Cruise Along the Coast of Portland Maine

(4.8 of 92 reviews)

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

Free Cancellation
Start From $75.00
 
Sunset Windjammer Cruise Along the Coast of Portland Maine Likely to Sell Out

Sunset Windjammer Cruise Along the Coast of Portland Maine

  • North America
  • Superb92 reviews4.8

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to exper....

    Free Cancellation
    Start From $75.00
 
 

2-Hour Private Luxury Boat Tour in New York City

(5 of 77 reviews)

Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manhattan aboard a 30' luxurious powerboat. Get an unobstructed view of the Manhattan skyline, Freedom Tower, Brooklyn Bridge, Empire ... More

Free Cancellation
Private Tour
Start From $499.99
 
2-Hour Private Luxury Boat Tour in New York City Likely to Sell Out

2-Hour Private Luxury Boat Tour in New York City

  • North America
  • Superb77 reviews5

Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manh....

    Free Cancellation
    Private Tour
    Start From $499.99
 
 

Chicago's Fireworks Show aboard Tall Ship Windy!

(5 of 6 reviews)

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a lei... More

Free Cancellation
Private Tour
Start From $113.73
 
Chicago's Fireworks Show aboard Tall Ship Windy! Likely to Sell Out

Chicago's Fireworks Show aboard Tall Ship Windy!

  • North America
  • Superb6 reviews5

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Na....

    Free Cancellation
    Private Tour
    Start From $113.73
 
 

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

(4.7 of 150 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
  • Superb150 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
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 692 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
  • Superb692 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
 
 

Seattle Sailing Experience BYOB

(5 of 128 reviews)

This is a boat ride like nothing else in Seattle! Our 70ft custom built sailboats were created to race around the world, and now are perfectly at home on Puget Sound. Sit back and relax as our trained crew hoist the sails and turn... More

Free Cancellation
Private Tour
Start From $60.00
 
Seattle Sailing Experience BYOB Likely to Sell Out

Seattle Sailing Experience BYOB

  • North America
  • Superb128 reviews5

This is a boat ride like nothing else in Seattle! Our 70ft custom built sailboats were created to ra....

    Free Cancellation
    Private Tour
    Start From $60.00
 
 

Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

(4.8 of 1,988 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

Special Offer
Free Cancellation
Private Tour
Start From $92.65
(Saving 15% ) $109.00
 
-15% 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
  • Superb1,988 reviews4.8

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $92.65
    (Saving 15% ) $109.00
 
 

Private Luxury Yacht Charters, BYOB & Dolphins

(5 of 379 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 $499.00
 
Private Luxury Yacht Charters, BYOB & Dolphins Likely to Sell Out

Private Luxury Yacht Charters, BYOB & Dolphins

  • North America
  • Superb379 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 $499.00
 
 

Snorkel Sail Adventure off Ka'anapali Beach, Maui

(4.9 of 24 reviews)

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buff... More

Free Cancellation
Private Tour
Start From $183.08
 
Snorkel Sail Adventure off Ka'anapali Beach, Maui Likely to Sell Out

Snorkel Sail Adventure off Ka'anapali Beach, Maui

  • North America
  • Superb24 reviews4.9

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....

    Free Cancellation
    Private Tour
    Start From $183.08
 
 

Waikiki Sunset Cocktail Sail with Open Bar

(4.8 of 500 reviews)

This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruise! Strangers become fast friends on this one regardless if your cruising solo or with a crew! We provide juice, soda, bottled wate... More

Free Cancellation
Private Tour
Start From $84.77
 
Waikiki Sunset Cocktail Sail with Open Bar Likely to Sell Out

Waikiki Sunset Cocktail Sail with Open Bar

  • North America
  • Superb500 reviews4.8

This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruis....

    Free Cancellation
    Private Tour
    Start From $84.77
 
 

Newport Sunset Sail on Schooner Adirondack

(4.9 of 54 reviews)

Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! 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 sailbo... More

Free Cancellation
Private Tour
Start From $67.84
 
Newport Sunset Sail on Schooner Adirondack Likely to Sell Out

Newport Sunset Sail on Schooner Adirondack

  • North America
  • Superb54 reviews4.9

Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of th....

    Free Cancellation
    Private Tour
    Start From $67.84
 
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