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Top 10 Best USA Sailing Trips

Found 421 Sailing Trips activities in USA. Sort by Popularity. - Page 4
 
-10% America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

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

(4.6 of 498 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

Special Offer
Free Cancellation
Start From $47.65
(Saving 10% ) $52.95
 
-10% America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

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

  • USA
  • Superb498 reviews4.6

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

    Special Offer
    Free Cancellation
    Start From $47.65
    (Saving 10% ) $52.95
 
 
-10% Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

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

(4.7 of 146 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

Special Offer
Free Cancellation
Start From $62.95
(Saving 10% ) $69.95
 
-10% Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

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

  • USA
  • Superb146 reviews4.7

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

    Special Offer
    Free Cancellation
    Start From $62.95
    (Saving 10% ) $69.95
 
 

Buccaneer Pirate Cruise in Destin

(4.9 of 89 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
Start From $55.00
 
Buccaneer Pirate Cruise in Destin

Buccaneer Pirate Cruise in Destin

  • USA
  • Superb89 reviews4.9

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

    Free Cancellation
    Start From $55.00
 
 

Sunset Lighthouse Cruise Along Casco Bay

(4.8 of 35 reviews)

Embark on an unforgettable 1.5-hour cruise along Maine's breathtaking coastline at sunset. See four of Maine's most iconic lighthouses, spot seals and seabirds, and take in the historic forts that dot the landscape. Bring your fav... More

Free Cancellation
Start From $67.00
 
Sunset Lighthouse Cruise Along Casco Bay

Sunset Lighthouse Cruise Along Casco Bay

  • USA
  • Superb35 reviews4.8

Embark on an unforgettable 1.5-hour cruise along Maine's breathtaking coastline at sunset. See four ....

    Free Cancellation
    Start From $67.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 243 reviews)

A three hour tour you won't want to miss! 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 adve... More

Free Cancellation
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument

Afternoon Sail & Snorkel to the Captain Cook Monument

  • USA
  • Superb243 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....

    Free Cancellation
    Start From $136.19
 
 

Newport Sightseeing Day Sailing Experience on Schooner Adirondack

(4.9 of 67 reviews)

See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schooner Adirondack. You'll pass by many iconic sights, bridges, lighthouses and more during this 1.5-hour experience!... More

Free Cancellation
Start From $57.24
 
Newport Sightseeing Day Sailing Experience on Schooner Adirondack Likely to Sell Out

Newport Sightseeing Day Sailing Experience on Schooner Adirondack

  • USA
  • Superb67 reviews4.9

See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schoone....

    Free Cancellation
    Start From $57.24
 
 

Newport Afternoon Sightseeing Sail on Classic Sailboat

(4.8 of 142 reviews)

Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narragansett Bay. Pass by many iconic sights during the sail, including Newport's historic lighthouses and landmarks, bridges, mansions a... More

Free Cancellation
Start From $57.24
 
Newport Afternoon Sightseeing Sail on Classic Sailboat Likely to Sell Out

Newport Afternoon Sightseeing Sail on Classic Sailboat

  • USA
  • Superb142 reviews4.8

Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narraga....

    Free Cancellation
    Start From $57.24
 
 

Schooner Fame Sailing Tour

(4.9 of 562 reviews)

FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per TripAdvisor. Don't miss the very best of what Salem has to offer! There's more to our town than witches! FAME is a full-scale replica... More

Free Cancellation
Start From $50.65
 
Schooner Fame Sailing Tour Likely to Sell Out

Schooner Fame Sailing Tour

  • USA
  • Superb562 reviews4.9

FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per Trip....

    Free Cancellation
    Start From $50.65
 
 

Catamaran Sunset Sail Premium 2.5hr Small group w/ drinks

(4.9 of 198 reviews)

Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and lounging around watching sea life, and water rush by. The swift and stable ocean design ensures a comfortable, and exhilarating ride wit... More

Free Cancellation
Start From $119.00
 
Catamaran Sunset Sail Premium 2.5hr Small group w/ drinks Likely to Sell Out

Catamaran Sunset Sail Premium 2.5hr Small group w/ drinks

  • USA
  • Superb198 reviews4.9

Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and loungi....

    Free Cancellation
    Start From $119.00
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.9 of 110 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

Free Cancellation
Start From $125.00
 
2-Hour Oahu Sunset Catamaran Sail Likely to Sell Out

2-Hour Oahu Sunset Catamaran Sail

  • USA
  • Superb110 reviews4.9

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

    Free Cancellation
    Start From $125.00
 
 

San Francisco Bay Sailing Cruise

(4.9 of 626 reviews)

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sail away from bustling city and enjoy photo ops from the vantage point of the water. You’ll coast past the city skyline, the Gold... More

Free Cancellation
Start From $72.00
 
San Francisco Bay Sailing Cruise Likely to Sell Out

San Francisco Bay Sailing Cruise

  • USA
  • Superb626 reviews4.9

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sa....

    Free Cancellation
    Start From $72.00
 
 

Newport Sunset Sail on Schooner Adirondack

(4.9 of 79 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
Start From $67.84
 
Newport Sunset Sail on Schooner Adirondack Likely to Sell Out

Newport Sunset Sail on Schooner Adirondack

  • USA
  • Superb79 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
    Start From $67.84
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.9 of 145 reviews)

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views o... More

Free Cancellation
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks Likely to Sell Out

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • USA
  • Superb145 reviews4.9

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....

    Free Cancellation
    Start From $61.50
 
 

Sunset Cocktail Cruise from Anaeho'omalu Bay

(4.8 of 60 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohala Coast aboard our legendary sailing catamaran Seasmoke. This cruise includes unlimited soft drinks, tropical juices, beers, wines... More

Free Cancellation
Start From $165.00
 
Sunset Cocktail Cruise from Anaeho'omalu Bay Likely to Sell Out

Sunset Cocktail Cruise from Anaeho'omalu Bay

  • USA
  • Superb60 reviews4.8

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....

    Free Cancellation
    Start From $165.00
 
 

Private Classic Sailboat Tour in New York City

(5 of 1 review)

This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a unique and immersive experience on the Hudson River. You'll enjoy stunning views of iconic landmarks like the Statue of Liberty, E... More

Free Cancellation
Private Tour
Start From $800.00
 
Private Classic Sailboat Tour in New York City Likely to Sell Out

Private Classic Sailboat Tour in New York City

  • USA
  • Superb1 review5

This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a ....

    Free Cancellation
    Private Tour
    Start From $800.00
 
 

Key West Reef Snorkel & Sail Adventure

(4.7 of 533 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
Private Tour
Start From $79.00
 
Key West Reef Snorkel & Sail Adventure Likely to Sell Out

Key West Reef Snorkel & Sail Adventure

  • USA
  • Superb533 reviews4.7

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

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Southwest Florida Sunset Sail

(4.9 of 452 reviews)

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft. Sailing Catamaran, "Copacetic". The sunset hours are a magical time to be out on the water. With the winds calm, the sun turns g... More

Free Cancellation
Private Tour
Start From $70.00
 
Southwest Florida Sunset Sail Likely to Sell Out

Southwest Florida Sunset Sail

  • USA
  • Superb452 reviews4.9

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft....

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

(4.7 of 147 reviews)

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty of interesting whale information Convenient location walking... More

Free Cancellation
Private Tour
Start From $79.00
 
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed Likely to Sell Out

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

  • USA
  • Superb147 reviews4.7

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well a....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Sunset Sailing Cruise in Monterey Bay

(4.8 of 34 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
Private Tour
Start From $95.00
 
Sunset Sailing Cruise in Monterey Bay Likely to Sell Out

Sunset Sailing Cruise in Monterey Bay

  • USA
  • Superb34 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Daytime Sailing Along San Diego's Skyline

(4.9 of 145 reviews)

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor Sunroad Marina on Harbor Island on San Diego Bay, we often s... More

Free Cancellation
Private Tour
Start From $89.00
 
Daytime Sailing Along San Diego's Skyline Likely to Sell Out

Daytime Sailing Along San Diego's Skyline

  • USA
  • Superb145 reviews4.9

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....

    Free Cancellation
    Private Tour
    Start From $89.00
 
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