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Top 10 Best North America Sailing Trips

Found 668 Sailing Trips activities in North America. Sort by Popularity. - Page 4
 

Deluxe Sunset & Day Sail Small Group

(5 of 129 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
  • Superb129 reviews5

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

    Free Cancellation
    Start From $119.00
 
 

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

(4.9 of 1,419 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

Free Cancellation
Start From $29.00
 
1-Hour Interactive Pirate Cruise (arrive 30 minutes early) Likely to Sell Out

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

  • North America
  • Superb1,419 reviews4.9

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

    Free Cancellation
    Start From $29.00
 
 

Sunset Sailing Cruise in Monterey Bay

(5 of 12 reviews)

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience Monterey Bay. Departing daily, 90 minutes before sunset, this dreamy 1.5-... More

Free Cancellation
Start From $95.00
 
Sunset Sailing Cruise in Monterey Bay Likely to Sell Out

Sunset Sailing Cruise in Monterey Bay

  • North America
  • Superb12 reviews5

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is....

    Free Cancellation
    Start From $95.00
 
 

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

(4.6 of 436 reviews)

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by the famous Dennis Connor. All trips take place under full sail. We only use our motor to get in a... More

Free Cancellation
Start From $52.95
 
America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head Likely to Sell Out

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

  • North America
  • Superb436 reviews4.6

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, S....

    Free Cancellation
    Start From $52.95
 
 

Key West Reef Snorkel & Sail Adventure

(4.7 of 509 reviews)

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Free Cancellation
Start From $79.00
 
Key West Reef Snorkel & Sail Adventure Likely to Sell Out

Key West Reef Snorkel & Sail Adventure

  • North America
  • Superb509 reviews4.7

Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....

    Free Cancellation
    Start From $79.00
 
 

Sunset Sip and Sail Key West with Open Bar and Live Music

(4.5 of 261 reviews)

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • Great Appetizers Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally... More

Free Cancellation
Start From $79.95
 
Sunset Sip and Sail Key West with Open Bar and Live Music Likely to Sell Out

Sunset Sip and Sail Key West with Open Bar and Live Music

  • North America
  • Exellent261 reviews4.5

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....

    Free Cancellation
    Start From $79.95
 
 

Sunset Sail from Ma'alaea Harbor

(4.6 of 207 reviews)

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our  luxury sailing catamaran, Ocean Spirit. It’s the perfect way to ex... More

Free Cancellation
Start From $151.00
 
Sunset Sail from Ma'alaea Harbor Likely to Sell Out

Sunset Sail from Ma'alaea Harbor

  • North America
  • Superb207 reviews4.6

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....

    Free Cancellation
    Start From $151.00
 
 

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

(4.8 of 141 reviews)

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More

Free Cancellation
Start From $120.69
 
Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun Likely to Sell Out

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

  • North America
  • Superb141 reviews4.8

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....

    Free Cancellation
    Start From $120.69
 
 

San Francisco Bay Cruise

(4.4 of 262 reviews)

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour excursion heads underneath the Golden Gate Bridge, around Alcatraz Island, past Angel Island State Park, and alongside the cit... More

Free Cancellation
Start From $38.00
 
San Francisco Bay Cruise Likely to Sell Out

San Francisco Bay Cruise

  • North America
  • Exellent262 reviews4.4

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hou....

    Free Cancellation
    Start From $38.00
 
 

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

(4.9 of 154 reviews)

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More

Free Cancellation
Start From $49.99
 
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast Likely to Sell Out

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

  • North America
  • Superb154 reviews4.9

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....

    Free Cancellation
    Start From $49.99
 
 

Pau Hana Sunset Cocktail Cruise

(4.8 of 48 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed catamaran. This cruise includes unlimited soft drinks, tropical juices, beers, wines, cocktails and a variety of appetizers.. Great f... More

Free Cancellation
Start From $165.00
 
Pau Hana Sunset Cocktail Cruise Likely to Sell Out

Pau Hana Sunset Cocktail Cruise

  • North America
  • Superb48 reviews4.8

Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed cat....

    Free Cancellation
    Start From $165.00
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 755 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

Free Cancellation
Start From $148.57
 
Sunset and Manta Ray Snorkel Adventure Likely to Sell Out

Sunset and Manta Ray Snorkel Adventure

  • North America
  • Superb755 reviews4.9

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

    Free Cancellation
    Start From $148.57
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 433 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... More

Free Cancellation
Start From $179.27
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb433 reviews4.9

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

    Free Cancellation
    Start From $179.27
 
 

New York Sunset Schooner Cruise on the Hudson River

(4.9 of 200 reviews)

Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known as Schooner Adirondack - inspired by the pilot schooners of... More

Free Cancellation
Start From $90.12
 
New York Sunset Schooner Cruise on the Hudson River Likely to Sell Out

New York Sunset Schooner Cruise on the Hudson River

  • North America
  • Superb200 reviews4.9

Experience a New York City sunset from the water on this evening sightseeing sail past many famous w....

    Free Cancellation
    Start From $90.12
 
 

2Hr Private Boat Tour Miami Beach, Captain & Champagne, & Sandbar

(4.8 of 264 reviews)

Get ready for the ultimate party experience on our 22ft boat in Miami Beach, perfect for groups of friends, bachelorette parties, and anyone looking to celebrate in style. Cruise the sparkling waters of Miami while enjoying your ... More

Free Cancellation
Private Tour
Start From $375.00
 
2Hr Private Boat Tour Miami Beach, Captain & Champagne, & Sandbar Likely to Sell Out

2Hr Private Boat Tour Miami Beach, Captain & Champagne, & Sandbar

  • North America
  • Superb264 reviews4.8

Get ready for the ultimate party experience on our 22ft boat in Miami Beach, perfect for groups of f....

    Free Cancellation
    Private Tour
    Start From $375.00
 
 

Adults only Sunset Cruise from Key West with Champagne

(4.9 of 891 reviews)

Get out on Key West’s beautiful shallow waters on the Adults Only sunset cruise, to sip Moët & Chandon champagne while enjoying the sunset. Included in the tour price are the house champagne Chandon Brut, 7 premium red and whit... More

Free Cancellation
Private Tour
Start From $108.91
 
Adults only Sunset Cruise from Key West with Champagne Likely to Sell Out

Adults only Sunset Cruise from Key West with Champagne

  • North America
  • Superb891 reviews4.9

Get out on Key West’s beautiful shallow waters on the Adults Only sunset cruise, to sip Moët & Ch....

    Free Cancellation
    Private Tour
    Start From $108.91
 
 

2-Hour Sunset Sail on the San Francisco Bay

(4.8 of 359 reviews)

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous traditional vessel to take in the sights at the most bewitching time of d... More

Free Cancellation
Private Tour
Start From $129.00
 
2-Hour Sunset Sail on the San Francisco Bay Likely to Sell Out

2-Hour Sunset Sail on the San Francisco Bay

  • North America
  • Superb359 reviews4.8

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Buccaneer Pirate Cruise

(5 of 44 reviews)

Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family! Enjoy a fun cruise with interactive pirate-themed activities, entertainment, and treasure hunts. Take in the beauty of the Emeral... More

Free Cancellation
Private Tour
Start From $55.00
 
Buccaneer Pirate Cruise Likely to Sell Out

Buccaneer Pirate Cruise

  • North America
  • Superb44 reviews5

Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family!....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

JFarwell Sunset Wine and Cheese Yacht Sailing

(4.9 of 116 reviews)

Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to invite our guests to be involved in sailing - take the helm, hoist the sails, or sit back and enjoy the beautiful sights and wines ... More

Free Cancellation
Private Tour
Start From $147.75
 
JFarwell Sunset Wine and Cheese Yacht Sailing Likely to Sell Out

JFarwell Sunset Wine and Cheese Yacht Sailing

  • North America
  • Superb116 reviews4.9

Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to i....

    Free Cancellation
    Private Tour
    Start From $147.75
 
 

BYOB Waikiki Sunset Swim and Diamond Head Sailing

(5 of 148 reviews)

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Free Cancellation
Private Tour
Start From $79.00
 
BYOB Waikiki Sunset Swim and Diamond Head Sailing Likely to Sell Out

BYOB Waikiki Sunset Swim and Diamond Head Sailing

  • North America
  • Superb148 reviews5

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....

    Free Cancellation
    Private Tour
    Start From $79.00
 
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