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Top 10 Best USA Sailing Trips

Found 450 Sailing Trips activities in USA. Sort by Popularity. - Page 2
 

Kauai’s Na Pali Coast Snorkel and Sail Tour

(4.8 of 565 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

  • USA
  • Superb565 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 151 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

  • USA
  • Superb151 reviews4.9

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

    Free Cancellation
    Start From $50.00
 
 

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

(4.9 of 1,996 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"

  • USA
  • Superb1,996 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 Snorkeling Tour with Free Pickup

(4.8 of 192 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 $95.00
 
Waikiki Turtle Snorkeling Tour with Free Pickup Likely to Sell Out

Waikiki Turtle Snorkeling Tour with Free Pickup

  • USA
  • Superb192 reviews4.8

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

    Free Cancellation
    Start From $95.00
 
 

2.5-Hour Small-Group Catamaran Sail with Drinks

(5 of 280 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

  • USA
  • Superb280 reviews5

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

    Free Cancellation
    Start From $119.00
 
 

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

  • USA
  • 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
 
 

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

(4.8 of 22 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

  • USA
  • Superb22 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 645 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

  • USA
  • Superb645 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
 
 

Private Luxury Yacht Charters, BYOB & Dolphins

(5 of 412 reviews)

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the water on one of our sailboats. We offer hourly, daily, or customized tours according to you... More

Free Cancellation
Private Tour
Start From $525.00
 
Private Luxury Yacht Charters, BYOB & Dolphins Likely to Sell Out

Private Luxury Yacht Charters, BYOB & Dolphins

  • USA
  • Superb412 reviews5

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the....

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

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

(4.1 of 607 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
Private Tour
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

  • USA
  • Exellent607 reviews4.1

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

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

Buccaneer Pirate Cruise in Destin

(4.8 of 117 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 in Destin Likely to Sell Out

Buccaneer Pirate Cruise in Destin

  • USA
  • Superb117 reviews4.8

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
 
 

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

(4.6 of 746 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

Free Cancellation
Private Tour
Start From $89.00
 
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas Likely to Sell Out

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

  • USA
  • Superb746 reviews4.6

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

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

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

(4.9 of 935 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
Private Tour
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

  • USA
  • Superb935 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $54.99
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 832 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
Private Tour
Start From $213.41
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • USA
  • Superb832 reviews4.7

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

    Free Cancellation
    Private Tour
    Start From $213.41
 
 

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

(4.6 of 117 reviews)

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vess... More

Free Cancellation
Private Tour
Start From $34.95
 
Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast Likely to Sell Out

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

  • USA
  • Superb117 reviews4.6

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....

    Free Cancellation
    Private Tour
    Start From $34.95
 
 

'Alihilani Lahaina Sunset Sail

(4.9 of 123 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

Free Cancellation
Private Tour
Start From $117.30
 
'Alihilani Lahaina Sunset Sail Likely to Sell Out

'Alihilani Lahaina Sunset Sail

  • USA
  • Superb123 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $117.30
 
 

Boston Harbor Sunset Sail Tour

(4.8 of 142 reviews)

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. This elegant sailing experience will be aboard either Schooner Adirondack III or Adir... More

Free Cancellation
Private Tour
Start From $82.27
 
Boston Harbor Sunset Sail Tour Likely to Sell Out

Boston Harbor Sunset Sail Tour

  • USA
  • Superb142 reviews4.8

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront ....

    Free Cancellation
    Private Tour
    Start From $82.27
 
 

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

(4.9 of 1,443 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
Private Tour
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

  • USA
  • Superb1,443 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $135.00
 
 

Newport Sunset Sail on Schooner Adirondack

(4.9 of 90 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

Free Cancellation
Private Tour
Start From $67.84
 
Newport Sunset Sail on Schooner Adirondack Likely to Sell Out

Newport Sunset Sail on Schooner Adirondack

  • USA
  • Superb90 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $67.84
 
 

Key West Afternoon Reef Snorkeling with Open Bar

(4.4 of 453 reviews)

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key West living reef where you will see coral and tropical fish. All snorkeling equipment is provided an... More

Free Cancellation
Private Tour
Start From $59.95
 
Key West Afternoon Reef Snorkeling with Open Bar Likely to Sell Out

Key West Afternoon Reef Snorkeling with Open Bar

  • USA
  • Exellent453 reviews4.4

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....

    Free Cancellation
    Private Tour
    Start From $59.95
 
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