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Top 10 Best North America Sailing Trips

Found 672 Sailing Trips activities in North America. Sort by Popularity. - Page 9
 

Half-Day Deluxe Molokini Snorkel Excursion in Maui

(4.9 of 78 reviews)

Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snorkeling trips, romantic sunset cruises, and everything in between. We’re honored to play a part in introducing our visitors to th... More

Free Cancellation
Start From $289.00
 
Half-Day Deluxe Molokini Snorkel Excursion in Maui

Half-Day Deluxe Molokini Snorkel Excursion in Maui

  • North America
  • Superb78 reviews4.9

Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snor....

    Free Cancellation
    Start From $289.00
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.8 of 58 reviews)

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More

Free Cancellation
Start From $179.00
 
Hawaiian Canoe Sailing Experience in Maui

Hawaiian Canoe Sailing Experience in Maui

  • North America
  • Superb58 reviews4.8

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....

    Free Cancellation
    Start From $179.00
 
 

Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

(5 of 28 reviews)

Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht regattas. Fate is not only the most demanded but also the largest and nicest sailing yacht available for Charter in Charleston, kn... More

Free Cancellation
Private Tour
Start From $599.00
 
Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

  • North America
  • Superb28 reviews5

Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht ....

    Free Cancellation
    Private Tour
    Start From $599.00
 
 

2.5-hour Guided Sailboat Tour

(4.9 of 168 reviews)

2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, 159 Bridge Park Drive. Views of the Brooklyn Bridge, Statue of Liberty, World Trade Center, Ellis Island, Governor's Island and M... More

Free Cancellation
Private Tour
Start From $118.00
 
2.5-hour Guided Sailboat Tour Likely to Sell Out

2.5-hour Guided Sailboat Tour

  • North America
  • Superb168 reviews4.9

2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, ....

    Free Cancellation
    Private Tour
    Start From $118.00
 
 

Isla Mujeres, Cancún Private Sunset Trip

(5 of 73 reviews)

Our tours are suited to your needs, as we want you to enjoy yourself, to simply let go, to watch the sunset and experience the moment. We are here to bring you the the quality service you so rightly deserve. Our adored crew ensure... More

Free Cancellation
Private Tour
Start From $450.00
 
Isla Mujeres, Cancún Private Sunset Trip Likely to Sell Out

Isla Mujeres, Cancún Private Sunset Trip

  • North America
  • Superb73 reviews5

Our tours are suited to your needs, as we want you to enjoy yourself, to simply let go, to watch the....

    Free Cancellation
    Private Tour
    Start From $450.00
 
 

Newport Afternoon Sightseeing Sail on Classic Sailboat

(4.8 of 59 reviews)

Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narragansett Bay. Pass by many iconic sights during the sail, including Newport's historic lighthouses and landmarks, bridges, mansions a... More

Free Cancellation
Private Tour
Start From $57.24
 
Newport Afternoon Sightseeing Sail on Classic Sailboat Likely to Sell Out

Newport Afternoon Sightseeing Sail on Classic Sailboat

  • North America
  • Superb59 reviews4.8

Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narraga....

    Free Cancellation
    Private Tour
    Start From $57.24
 
 

Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani

(4.8 of 35 reviews)

Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. This 1.5-hour journey from Honokohau Harbor offers a chance to bask in the sun and enjoy the ocean breeze while taking in the breath... More

Free Cancellation
Private Tour
Start From $117.76
 
Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani Likely to Sell Out

Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani

  • North America
  • Superb35 reviews4.8

Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. Th....

    Free Cancellation
    Private Tour
    Start From $117.76
 
 

Sailing Charters in Wilmington

(5 of 147 reviews)

After a successful first season I am happy to be here for back to back seasons. Sail in style on the historic Wilmington river walk. Enjoy a personalized Charter experience with up to six guests. Very few sailboats are up for publ... More

Free Cancellation
Private Tour
Start From $89.99
 
Sailing Charters in Wilmington Likely to Sell Out

Sailing Charters in Wilmington

  • North America
  • Superb147 reviews5

After a successful first season I am happy to be here for back to back seasons. Sail in style on the....

    Free Cancellation
    Private Tour
    Start From $89.99
 
 

Polynesian Canoe Sunset Sail

(4.9 of 118 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Free Cancellation
Private Tour
Start From $250.00
 
Polynesian Canoe Sunset Sail Likely to Sell Out

Polynesian Canoe Sunset Sail

  • North America
  • Superb118 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Free Cancellation
    Private Tour
    Start From $250.00
 
 

Hear the whales! World class whale watching!

(4.8 of 5 reviews)

Your whale watching tour in Cabo San Lucas will become magical with the help of professional-grade hydrophones. If whales are communicating, you may be lucky to get the rare opportunity to hear the whale songs live! Our RABEN (Me... More

Free Cancellation
Private Tour
Start From $99.00
 
Hear the whales! World class whale watching! Likely to Sell Out

Hear the whales! World class whale watching!

  • North America
  • Superb5 reviews4.8

Your whale watching tour in Cabo San Lucas will become magical with the help of professional-grade h....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline

(4.9 of 21 reviews)

Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Miami Beach experience. Connect with nature, discover new landscapes, & create lasting memories as you explore the stunning coastline... More

Free Cancellation
Private Tour
Start From $600.00
 
Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline Likely to Sell Out

Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline

  • North America
  • Superb21 reviews4.9

Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Mia....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

52' Yacht Rental in Miami Beach with Experienced Captain

(4 of 6 reviews)

Enjoy the day on the water with friends & family in Miami Beach with Dolphin Water Sport. Our +950 reviews on Google with a 4.9 score guarantee our quality. Our Yacht & Captains are certified & licensed by the USCG, giving you a... More

Free Cancellation
Private Tour
Start From $1,500.00
 
52' Yacht Rental in Miami Beach with Experienced Captain Likely to Sell Out

52' Yacht Rental in Miami Beach with Experienced Captain

  • North America
  • Very Good6 reviews4

Enjoy the day on the water with friends & family in Miami Beach with Dolphin Water Sport. Our +950 ....

    Free Cancellation
    Private Tour
    Start From $1,500.00
 
 

Skagway Trail and Sail

(5 of 3 reviews)

This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike Electric Bicycles where you will join us for a self-guided ride to some of Skagway's best sites! You will visit a waterfall, scenic... More

Free Cancellation
Private Tour
Start From $265.00
 
Skagway Trail and Sail Likely to Sell Out

Skagway Trail and Sail

  • North America
  • Superb3 reviews5

This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike E....

    Free Cancellation
    Private Tour
    Start From $265.00
 
 

Premium Isla Mujeres Tour by Private Catamaran

(5 of 105 reviews)

We specialize in making this all-day trip unique, a unique and beautiful experience for all our guests. This trip can always be customized as desired, as we offer 2 options to our customers. Our trained team is always there to pro... More

Free Cancellation
Private Tour
Start From $800.00
 
Premium Isla Mujeres Tour by Private Catamaran Likely to Sell Out

Premium Isla Mujeres Tour by Private Catamaran

  • North America
  • Superb105 reviews5

We specialize in making this all-day trip unique, a unique and beautiful experience for all our gues....

    Free Cancellation
    Private Tour
    Start From $800.00
 
 

2hr. SUNSET Sailing Experience on San Francisco Bay

(5 of 15 reviews)

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sailing Experience is "interactive" which means we want you to get the full experience of sailing so you'll have an opportunity to tak... More

Free Cancellation
Private Tour
Start From $149.00
 
2hr. SUNSET Sailing Experience on San Francisco Bay Likely to Sell Out

2hr. SUNSET Sailing Experience on San Francisco Bay

  • North America
  • Superb15 reviews5

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sail....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Sunset Cruise in Los Cabos with Jazz and Wine

(4.7 of 190 reviews)

Cruise the Los Cabo's Coastline while listening to smooth jazz and instrumental aboard the Tropicat. Your tour also features an international bar and a meat & cheese selection as you sail past main landmarks such as Lover's Beach,... More

Free Cancellation
Private Tour
Start From $133.00
 
Sunset Cruise in Los Cabos with Jazz and Wine Likely to Sell Out

Sunset Cruise in Los Cabos with Jazz and Wine

  • North America
  • Superb190 reviews4.7

Cruise the Los Cabo's Coastline while listening to smooth jazz and instrumental aboard the Tropicat.....

    Free Cancellation
    Private Tour
    Start From $133.00
 
 

Private Customizable Sailing Tour in Cancun

(4.7 of 115 reviews)

Enjoy a private sailing tour for just you and your party aboard a private sailboat which offers the opportunity to visit wonderful places that can only be known by the sea. From a relaxing private sailing tour in the bay of Can... More

Free Cancellation
Private Tour
Start From $549.34
 
Private Customizable Sailing Tour in Cancun Likely to Sell Out

Private Customizable Sailing Tour in Cancun

  • North America
  • Superb115 reviews4.7

Enjoy a private sailing tour for just you and your party aboard a private sailboat which offers th....

    Free Cancellation
    Private Tour
    Start From $549.34
 
 

Sunset Sail Tour

(4.9 of 84 reviews)

Take a 2.0 hour sailing cruise on a Sparkman and Stephens Sailing Yacht. With your small-group, engage on this classic 42 ft yacht, that accommodates a 6 passenger maximum for an intimate cruise through the waters of Wrightsvill... More

Free Cancellation
Private Tour
Start From $125.00
 
Sunset Sail Tour Likely to Sell Out

Sunset Sail Tour

  • North America
  • Superb84 reviews4.9

Take a 2.0 hour sailing cruise on a Sparkman and Stephens Sailing Yacht. With your small-group, enga....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Waikiki small group turtle snorkeling & sailing

(5 of 63 reviews)

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of dawn during their Hawaiian vacation due to time zone changes. As we start out our tour from ... More

Free Cancellation
Private Tour
Start From $99.00
 
Waikiki small group turtle snorkeling & sailing Likely to Sell Out

Waikiki small group turtle snorkeling & sailing

  • North America
  • Superb63 reviews5

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

New York City Sailboat Day Cruise to the Statue of Liberty

(4.9 of 120 reviews)

Experience New York by water on this 2-hour sail aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as the crew raises sail and the boat effortlessly glides a... More

Free Cancellation
Private Tour
Start From $71.63
 
New York City Sailboat Day Cruise to the Statue of Liberty Likely to Sell Out

New York City Sailboat Day Cruise to the Statue of Liberty

  • North America
  • Superb120 reviews4.9

Experience New York by water on this 2-hour sail aboard Schooner Adirondack, an 80-foot, 2-masted sc....

    Free Cancellation
    Private Tour
    Start From $71.63
 
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