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Top 10 Best North America Sailing Trips

Found 770 Sailing Trips activities in North America. Sort by Popularity. - Page 2
 

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

(4.7 of 1,581 reviews)

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look for dolphins, whales, and other marine critters as you sip a drink, snap som... More

Free Cancellation
Start From $222.86
 
Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

  • North America
  • Superb1,581 reviews4.7

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....

    Free Cancellation
    Start From $222.86
 
 

Kauai’s Na Pali Coast Snorkel and Sail Tour

(4.8 of 564 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
  • Superb564 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
 
 

Waikiki Sunset Boat Cruise

(4.9 of 147 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
  • Superb147 reviews4.9

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

    Free Cancellation
    Start From $50.00
 
 

Seattle Sailing Harbor Tour

(4.7 of 491 reviews)

Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing tour is family-friendly and is an excellent way to see the Seattle skyline, the beauty of the Puget Sound, even mountain views! We ... More

Free Cancellation
Start From $39.00
 
Seattle Sailing Harbor Tour Likely to Sell Out

Seattle Sailing Harbor Tour

  • North America
  • Superb491 reviews4.7

Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing t....

    Free Cancellation
    Start From $39.00
 
 

2 Hour Sailing Cruise on Lake Tahoe

(4.9 of 903 reviews)

Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing adventure and include complementary local beer and wine, as well as non-alcoholic beverages on all of our daily cruises. Unlike other t... More

Free Cancellation
Start From $149.00
 
2 Hour Sailing Cruise on Lake Tahoe Likely to Sell Out

2 Hour Sailing Cruise on Lake Tahoe

  • North America
  • Superb903 reviews4.9

Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing advent....

    Free Cancellation
    Start From $149.00
 
 

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

(4.9 of 1,993 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 Likely to Sell Out

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

  • North America
  • Superb1,993 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
 
 

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

(4.7 of 433 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 $24.99
 
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
  • Superb433 reviews4.7

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

    Free Cancellation
    Start From $24.99
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 831 reviews)

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More

Free Cancellation
Start From $213.41
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • North America
  • Superb831 reviews4.7

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....

    Free Cancellation
    Start From $213.41
 
 

1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

(4.1 of 605 reviews)

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises.... More

Free Cancellation
Start From $70.00
 
1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain Likely to Sell Out

1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

  • North America
  • Exellent605 reviews4.1

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....

    Free Cancellation
    Start From $70.00
 
 

Waikiki Turtle Snorkeling Tour with Free Pickup

(4.8 of 185 reviews)

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP), sea scooters, and more—offeri... More

Free Cancellation
Start From $90.00
 
Waikiki Turtle Snorkeling Tour with Free Pickup Likely to Sell Out

Waikiki Turtle Snorkeling Tour with Free Pickup

  • North America
  • Superb185 reviews4.8

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamara....

    Free Cancellation
    Start From $90.00
 
 

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

(4.9 of 933 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 $54.99
 
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
  • Superb933 reviews4.9

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

    Free Cancellation
    Start From $54.99
 
 

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

(4.8 of 21 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
  • Superb21 reviews4.8

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
 
 

Classic Tall Ship Cruise in Boston Harbor

(4.7 of 639 reviews)

Come out for a day sail adventure in Boston Harbor aboard one of our classic wooden schooners, Liberty Star or Fame. Get away from the hustle and bustle of the city streets and enjoy some quality time out on the water with unbeata... More

Free Cancellation
Start From $39.55
 
Classic Tall Ship Cruise in Boston Harbor Likely to Sell Out

Classic Tall Ship Cruise in Boston Harbor

  • North America
  • Superb639 reviews4.7

Come out for a day sail adventure in Boston Harbor aboard one of our classic wooden schooners, Liber....

    Free Cancellation
    Start From $39.55
 
 

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

(4.7 of 171 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
  • Superb171 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
 
 

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

(4.3 of 1,543 reviews)

Award Winning Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire the Spectacular marine life on this awarded Cozumel Snorkeling trip. Enjoy Cozumel's top attractions and most visited reefs in the Caribbean... More

Special Offer
Free Cancellation
Start From $58.50
(Saving 10% ) $65.00
 
-10% Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs Likely to Sell Out

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

  • North America
  • Exellent1,543 reviews4.3

Award Winning Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire the Specta....

    Special Offer
    Free Cancellation
    Start From $58.50
    (Saving 10% ) $65.00
 
 

2.5-Hour Small-Group Catamaran Sail with Drinks

(5 of 279 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

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

2.5-Hour Small-Group Catamaran Sail with Drinks

  • North America
  • Superb279 reviews5

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

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

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

(4.9 of 1,442 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

Special Offer
Free Cancellation
Start From $135.00
(Saving inf% ) $0.00
 
-inf% 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
  • Superb1,442 reviews4.9

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

    Special Offer
    Free Cancellation
    Start From $135.00
    (Saving inf% ) $0.00
 
 

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

(4.6 of 744 reviews)

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More

Special Offer
Free Cancellation
Start From $89.00
(Saving inf% ) $0.00
 
-inf% Key West Sunset Sail: Dolphin Watching, Wine, and Tapas Likely to Sell Out

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

  • North America
  • Superb744 reviews4.6

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....

    Special Offer
    Free Cancellation
    Start From $89.00
    (Saving inf% ) $0.00
 
 

Newport Sunset Sail on Schooner Adirondack

(4.9 of 87 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

Special Offer
Free Cancellation
Start From $67.84
(Saving inf% ) $0.00
 
-inf% Newport Sunset Sail on Schooner Adirondack Likely to Sell Out

Newport Sunset Sail on Schooner Adirondack

  • North America
  • Superb87 reviews4.9

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

    Special Offer
    Free Cancellation
    Start From $67.84
    (Saving inf% ) $0.00
 
 

'Alihilani Lahaina Sunset Sail

(4.9 of 117 reviews)

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for a luxurious experience, allowing for incredible views of Maui and the inter islands from the... More

Special Offer
Free Cancellation
Start From $117.30
(Saving inf% ) $0.00
 
-inf% 'Alihilani Lahaina Sunset Sail Likely to Sell Out

'Alihilani Lahaina Sunset Sail

  • North America
  • Superb117 reviews4.9

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....

    Special Offer
    Free Cancellation
    Start From $117.30
    (Saving inf% ) $0.00
 
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