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Top 10 Best North America Sailing Trips

Found 755 Sailing Trips activities in North America. Sort by Popularity. - Page 2
 

Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

(4.7 of 546 reviews)

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the ocean, with the iconic Waikiki coastline as your backdrop. As the sun begins to se... More

Free Cancellation
Start From $56.00
 
Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

  • North America
  • Superb546 reviews4.7

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....

    Free Cancellation
    Start From $56.00
 
 

Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail

(4.9 of 2,260 reviews)

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with premium drinks, indescribable views, and music. As we sail alongside Oa... More

Free Cancellation
Start From $89.99
 
Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail

Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail

  • North America
  • Superb2,260 reviews4.9

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....

    Free Cancellation
    Start From $89.99
 
 

Dolphin Sunset Cruise in Panama City Beach on the "Island Time"

(4.9 of 1,926 reviews)

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in Panama City Beach, FL. Enjoy a rum punch while cruising along the beautiful Gulf Coa... More

Free Cancellation
Start From $45.00
 
Dolphin Sunset Cruise in Panama City Beach on the

Dolphin Sunset Cruise in Panama City Beach on the "Island Time"

  • North America
  • Superb1,926 reviews4.9

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which....

    Free Cancellation
    Start From $45.00
 
 

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,680 reviews)

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island relaxation in one extraordinary outing. Swim among sea turtles and tropical fi... More

Free Cancellation
Start From $89.56
 
Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

  • North America
  • Superb1,680 reviews4.8

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This pop....

    Free Cancellation
    Start From $89.56
 
 

Kauai’s Na Pali Coast Snorkel and Sail Tour

(4.8 of 554 reviews)

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making it the top choice for fami... More

Free Cancellation
Start From $292.48
 
Kauai’s Na Pali Coast Snorkel and Sail Tour Likely to Sell Out

Kauai’s Na Pali Coast Snorkel and Sail Tour

  • North America
  • Superb554 reviews4.8

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour cat....

    Free Cancellation
    Start From $292.48
 
 

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

(4.9 of 829 reviews)

✨ Discover Los Cabos Like Never Before! Sail the turquoise waters of the Sea of Cortez on an unforgettable snorkeling, sightseeing and sailing adventure. Begin at Pelican’s Rock, dive into crystal-clear waters filled with hun... More

Free Cancellation
Start From $120.00
 
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
  • Superb829 reviews4.9

✨ Discover Los Cabos Like Never Before! Sail the turquoise waters of the Sea of Cortez on an unfor....

    Free Cancellation
    Start From $120.00
 
 

Key West's Favorite Afternoon Dolphin Sail

(4.6 of 180 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
  • Superb180 reviews4.6

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 in Key West with Beverages Included

(4.9 of 940 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
  • Superb940 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 268 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
  • Superb268 reviews5

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

    Free Cancellation
    Start From $119.00
 
 

Cabo Boat Ride to El Arco & Lover’s Beach with Swimming

(4.8 of 397 reviews)

Enjoy the perfect combination of sightseeing and beach time on this Cabo San Lucas boat ride to El Arco and Lover’s Beach. Cruise along the stunning coastline as you pass iconic landmarks like the Arch, Sea Lion Colony, and Peli... More

Free Cancellation
Start From $23.00
 
Cabo Boat Ride to El Arco & Lover’s Beach with Swimming Likely to Sell Out

Cabo Boat Ride to El Arco & Lover’s Beach with Swimming

  • North America
  • Superb397 reviews4.8

Enjoy the perfect combination of sightseeing and beach time on this Cabo San Lucas boat ride to El A....

    Free Cancellation
    Start From $23.00
 
 

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

(4.7 of 160 reviews)

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More

Free Cancellation
Start From $69.95
 
Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine Likely to Sell Out

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

  • North America
  • Superb160 reviews4.7

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....

    Free Cancellation
    Start From $69.95
 
 

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

(4.9 of 866 reviews)

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand K... More

Free Cancellation
Start From $122.59
 
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres Likely to Sell Out

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

  • North America
  • Superb866 reviews4.9

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in....

    Free Cancellation
    Start From $122.59
 
 

St. Augustine Live Music Sunset Sail with Drinks

(4.7 of 346 reviews)

Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sail! Indulge in complimentary beer, wine, soda, water, margaritas, champagne, and a snack, while enjoying live performances by some ... More

Free Cancellation
Start From $78.23
 
St. Augustine Live Music Sunset Sail with Drinks Likely to Sell Out

St. Augustine Live Music Sunset Sail with Drinks

  • North America
  • Superb346 reviews4.7

Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sai....

    Free Cancellation
    Start From $78.23
 
 

Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar

(4.7 of 14 reviews)

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that... More

Free Cancellation
Start From $203.16
 
Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar Likely to Sell Out

Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar

  • North America
  • Superb14 reviews4.7

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....

    Free Cancellation
    Start From $203.16
 
 

Waikiki Beach Sunset Catamaran: Cocktail Sail with Open Bar

(4.7 of 565 reviews)

Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This lively evening cruise invites solo travelers and groups alike to unwind with unlimited drinks—including Maui Brewing beers, wine... More

Free Cancellation
Start From $84.77
 
Waikiki Beach Sunset Catamaran: Cocktail Sail with Open Bar Likely to Sell Out

Waikiki Beach Sunset Catamaran: Cocktail Sail with Open Bar

  • North America
  • Superb565 reviews4.7

Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This ....

    Free Cancellation
    Start From $84.77
 
 

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

(4.9 of 1,423 reviews)

The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy ... More

Free Cancellation
Start From $135.00
 
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres Likely to Sell Out

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

  • North America
  • Superb1,423 reviews4.9

The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t ....

    Free Cancellation
    Start From $135.00
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 548 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 a... More

Free Cancellation
Start From $177.73
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb548 reviews4.9

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

    Free Cancellation
    Start From $177.73
 
 

2.5-Hour Small-Group Catamaran Sail with Drinks

(5 of 257 reviews)

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail. Designed for comfort and stability, these modern catamarans featu... More

Free Cancellation
Start From $119.00
 
2.5-Hour Small-Group Catamaran Sail with Drinks Likely to Sell Out

2.5-Hour Small-Group Catamaran Sail with Drinks

  • North America
  • Superb257 reviews5

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your ....

    Free Cancellation
    Start From $119.00
 
 

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

(4.9 of 883 reviews)

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985... More

Free Cancellation
Start From $49.99
 
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB Likely to Sell Out

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

  • North America
  • Superb883 reviews4.9

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....

    Free Cancellation
    Start From $49.99
 
 

Waikiki Sunset Boat Cruise

(4.9 of 117 reviews)

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More

Free Cancellation
Start From $50.00
 
Waikiki Sunset Boat Cruise Likely to Sell Out

Waikiki Sunset Boat Cruise

  • North America
  • Superb117 reviews4.9

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....

    Free Cancellation
    Start From $50.00
 
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