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Top 10 Best North America Sailing Trips

Found 765 Sailing Trips activities in North America. Sort by Popularity. - Page 8
 

Sandbar, Snorkel, and Sunset Sail in Key West

(4.5 of 11 reviews)

This trip combines three of the most sought-after experiences in Key West into one relaxed afternoon: extended time at a shallow-water sandbar, snorkeling in clear backcountry waters, and a sunset on the water. Sailing aboard a hi... More

Free Cancellation
Start From $135.00
 
Sandbar, Snorkel, and Sunset Sail in Key West

Sandbar, Snorkel, and Sunset Sail in Key West

  • North America
  • Exellent11 reviews4.5

This trip combines three of the most sought-after experiences in Key West into one relaxed afternoon....

    Free Cancellation
    Start From $135.00
 
 
-15% The Legendary Canadian Coastal Sail

The Legendary Canadian Coastal Sail

(5 of 255 reviews)

Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds with the breathtaking views of the Coastal and Tantalus mountain ranges. We will depart from the docks in Squamish (about 40 minut... More

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Start From $98.58
(Saving 15% ) $115.98
 
-15% The Legendary Canadian Coastal Sail

The Legendary Canadian Coastal Sail

  • North America
  • Superb255 reviews5

Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds w....

    Special Offer
    Free Cancellation
    Start From $98.58
    (Saving 15% ) $115.98
 
 
-inf% Seattle’s Original Sailing Cruise (Est. 1984) – 70ft Boat - BYOB

Seattle’s Original Sailing Cruise (Est. 1984) – 70ft Boat - BYOB

(4.9 of 199 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

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Start From $60.00
(Saving inf% ) $0.00
 
-inf% Seattle’s Original Sailing Cruise (Est. 1984) – 70ft Boat - BYOB

Seattle’s Original Sailing Cruise (Est. 1984) – 70ft Boat - B....

  • North America
  • Superb199 reviews4.9

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

    Special Offer
    Free Cancellation
    Start From $60.00
    (Saving inf% ) $0.00
 
 

Sailing Charters in Wilmington

(5 of 198 reviews)

After a successful first three seasons I am happy to be here for a fourth season!!! 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 ... More

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Free Cancellation
Start From $89.48
(Saving inf% ) $0.00
 
-inf% Sailing Charters in Wilmington Likely to Sell Out

Sailing Charters in Wilmington

  • North America
  • Superb198 reviews5

After a successful first three seasons I am happy to be here for a fourth season!!! Sail in style on....

    Special Offer
    Free Cancellation
    Start From $89.48
    (Saving inf% ) $0.00
 
 

America's Cup Evening Sailing Adventure Newport, RI

(4.9 of 42 reviews)

Get on board for the best hands-on sailing experience Newport, RI has to offer. A 2 hour sail around Narragansett Bay passed many iconic sights including New York Yacht Club, Ida Lewis Light, Fort Adams, Eisenhower House, Hammersm... More

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Start From $125.00
(Saving inf% ) $0.00
 
-inf% America's Cup Evening Sailing Adventure Newport, RI Likely to Sell Out

America's Cup Evening Sailing Adventure Newport, RI

  • North America
  • Superb42 reviews4.9

Get on board for the best hands-on sailing experience Newport, RI has to offer. A 2 hour sail around....

    Special Offer
    Free Cancellation
    Start From $125.00
    (Saving inf% ) $0.00
 
 

Snorkel with Manta Rays Guaranteed

(4.8 of 753 reviews)

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

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Free Cancellation
Start From $141.57
(Saving inf% ) $0.00
 
-inf% Snorkel with Manta Rays Guaranteed Likely to Sell Out

Snorkel with Manta Rays Guaranteed

  • North America
  • Superb753 reviews4.8

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....

    Special Offer
    Free Cancellation
    Start From $141.57
    (Saving inf% ) $0.00
 
 

Day Sail from Traverse City with Food, Wine, & Cocktails

(4.9 of 176 reviews)

For a full description please visit our website at https://www.winddancertc.com/ where you can learn about the vessel, crew, local history and make your bookings!... More

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Free Cancellation
Start From $189.00
(Saving inf% ) $0.00
 
-inf% Day Sail from Traverse City with Food, Wine, & Cocktails Likely to Sell Out

Day Sail from Traverse City with Food, Wine, & Cocktails

  • North America
  • Superb176 reviews4.9

For a full description please visit our website at https://www.winddancertc.com/ where you can learn....

    Special Offer
    Free Cancellation
    Start From $189.00
    (Saving inf% ) $0.00
 
 

Casco Bay Morning Windjammer Sail

(4.9 of 30 reviews)

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

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Free Cancellation
Start From $61.00
(Saving inf% ) $0.00
 
-inf% Casco Bay Morning Windjammer Sail Likely to Sell Out

Casco Bay Morning Windjammer Sail

  • North America
  • Superb30 reviews4.9

Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the per....

    Special Offer
    Free Cancellation
    Start From $61.00
    (Saving inf% ) $0.00
 
 

1-Hour Interactive Pirate Cruise (arrive 30 minutes early)

(4.9 of 1,526 reviews)

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along Florida’s Intracoastal Waterway that’s fun for the whole family! T... More

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Free Cancellation
Start From $35.00
(Saving inf% ) $0.00
 
-inf% 1-Hour Interactive Pirate Cruise (arrive 30 minutes early) Likely to Sell Out

1-Hour Interactive Pirate Cruise (arrive 30 minutes early)

  • North America
  • Superb1,526 reviews4.9

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure ....

    Special Offer
    Free Cancellation
    Start From $35.00
    (Saving inf% ) $0.00
 
 

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

(5 of 716 reviews)

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our shaded cabin or sunny splash nets. Snorkel calm waters and lush coral gardens u... More

Special Offer
Free Cancellation
Start From $189.00
(Saving inf% ) $0.00
 
-inf% Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure Likely to Sell Out

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

  • North America
  • Superb716 reviews5

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....

    Special Offer
    Free Cancellation
    Start From $189.00
    (Saving inf% ) $0.00
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 865 reviews)

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays!  Upon arriving, receive an in... More

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Free Cancellation
Start From $154.51
(Saving inf% ) $0.00
 
-inf% Sunset and Manta Ray Snorkel Adventure Likely to Sell Out

Sunset and Manta Ray Snorkel Adventure

  • North America
  • Superb865 reviews4.9

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....

    Special Offer
    Free Cancellation
    Start From $154.51
    (Saving inf% ) $0.00
 
 

Waikiki Fireworks Cocktail Cruise

(4.5 of 8 reviews)

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to remember.... More

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Free Cancellation
Start From $85.09
(Saving inf% ) $0.00
 
-inf% Waikiki Fireworks Cocktail Cruise Likely to Sell Out

Waikiki Fireworks Cocktail Cruise

  • North America
  • Exellent8 reviews4.5

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a b....

    Special Offer
    Free Cancellation
    Start From $85.09
    (Saving inf% ) $0.00
 
 

2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

(5 of 103 reviews)

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on the sea. 2.5 hour tour length is perfect for seeing all the beautiful sights. Catamarans reall... More

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Free Cancellation
Start From $119.00
(Saving inf% ) $0.00
 
-inf% 2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks Likely to Sell Out

2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

  • North America
  • Superb103 reviews5

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepare....

    Special Offer
    Free Cancellation
    Start From $119.00
    (Saving inf% ) $0.00
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.8 of 134 reviews)

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for ... More

Special Offer
Free Cancellation
Start From $130.00
(Saving inf% ) $0.00
 
-inf% 2-Hour Oahu Sunset Catamaran Sail Likely to Sell Out

2-Hour Oahu Sunset Catamaran Sail

  • North America
  • Superb134 reviews4.8

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran fr....

    Special Offer
    Free Cancellation
    Start From $130.00
    (Saving inf% ) $0.00
 
 

Spectacular Sunset Sail on San Diego Bay

(5 of 31 reviews)

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group, local captain sharing hidden stories, hands-on sailing, wildlife encounters, and unforgettable vistas of San Diego Bay. Participate or sit back and en... More

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Free Cancellation
Start From $108.00
(Saving inf% ) $0.00
 
-inf% Spectacular Sunset Sail on San Diego Bay Likely to Sell Out

Spectacular Sunset Sail on San Diego Bay

  • North America
  • Superb31 reviews5

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group, local captain sharin....

    Special Offer
    Free Cancellation
    Start From $108.00
    (Saving inf% ) $0.00
 
 

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

(4.8 of 220 reviews)

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More

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Free Cancellation
Start From $200.00
(Saving inf% ) $0.00
 
-inf% Molokini Snorkel and Performance Sail: Mā’alaea Harbor Likely to Sell Out

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

  • North America
  • Superb220 reviews4.8

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....

    Special Offer
    Free Cancellation
    Start From $200.00
    (Saving inf% ) $0.00
 
 

Sunset Dolphin Sail Aboard the Footloose Catamaran

(4.8 of 479 reviews)

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on SV Footloose, our 38 passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico ... More

Special Offer
Free Cancellation
Start From $45.00
(Saving inf% ) $0.00
 
-inf% Sunset Dolphin Sail Aboard the Footloose Catamaran Likely to Sell Out

Sunset Dolphin Sail Aboard the Footloose Catamaran

  • North America
  • Superb479 reviews4.8

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

    Special Offer
    Free Cancellation
    Start From $45.00
    (Saving inf% ) $0.00
 
 

JFarwell Moonlight Yacht Cruise from Halifax Waterfront

(4.8 of 49 reviews)

Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the Captain and passengers for a social sail - or laying on the bow relaxing under the stars, this moonlight sail is ultimate freedom! ... More

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Free Cancellation
Start From $72.94
(Saving inf% ) $0.00
 
-inf% JFarwell Moonlight Yacht Cruise from Halifax Waterfront Likely to Sell Out

JFarwell Moonlight Yacht Cruise from Halifax Waterfront

  • North America
  • Superb49 reviews4.8

Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the C....

    Special Offer
    Free Cancellation
    Start From $72.94
    (Saving inf% ) $0.00
 
 

El Cielo Cozumel Snorkeling trip by Catamaran

(4.4 of 284 reviews)

TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnificent reefs and great snorkeling and after, head back to a secluded Beach to relax and enjoy the beauty of Cozumel turquoise waters.... More

Special Offer
Free Cancellation
Start From $95.00
(Saving inf% ) $0.00
 
-inf% El Cielo Cozumel Snorkeling trip by Catamaran Likely to Sell Out

El Cielo Cozumel Snorkeling trip by Catamaran

  • North America
  • Exellent284 reviews4.4

TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnific....

    Special Offer
    Free Cancellation
    Start From $95.00
    (Saving inf% ) $0.00
 
 

Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

(4.9 of 350 reviews)

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with Captain Phil, a USCG-licensed captain with 55 years of sailing experience. ... More

Special Offer
Free Cancellation
Start From $125.00
(Saving inf% ) $0.00
 
-inf% Top Rated San Diego Sunset Sail Classic Yacht 6 Guests Likely to Sell Out

Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

  • North America
  • Superb350 reviews4.9

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San ....

    Special Offer
    Free Cancellation
    Start From $125.00
    (Saving inf% ) $0.00
 
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