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Top 10 Best USA Sailing Trips

Found 450 Sailing Trips activities in USA. Sort by Popularity. - Page 3
 

Best Private Luxury Daytime Boat Tour in New York City - 2 Hour

(5 of 93 reviews)

Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manhattan aboard a 30' luxurious powerboat. Get an unobstructed view of the Manhattan skyline, Freedom Tower, Brooklyn Bridge, Empire ... More

Free Cancellation
Private Tour
Start From $499.99
 
Best Private Luxury Daytime Boat Tour in New York City - 2 Hour

Best Private Luxury Daytime Boat Tour in New York City - 2 Hour

  • USA
  • Superb93 reviews5

Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manh....

    Free Cancellation
    Private Tour
    Start From $499.99
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.8 of 190 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 ... More

Free Cancellation
Private Tour
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • USA
  • Superb190 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $61.50
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 557 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
Private Tour
Start From $177.73
 
Deluxe Sail & Snorkel to the Captain Cook Monument

Deluxe Sail & Snorkel to the Captain Cook Monument

  • USA
  • Superb557 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $177.73
 
 

St. Augustine Live Music Sail with Drinks & Sunset Option

(4.7 of 362 reviews)

Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience! Opt for a two-hour live music sunset sail with all sails raised, or unwind on a 90-minute After Dark Live Music Cruise (no sailin... More

Free Cancellation
Private Tour
Start From $78.28
 
St. Augustine Live Music Sail with Drinks & Sunset Option Likely to Sell Out

St. Augustine Live Music Sail with Drinks & Sunset Option

  • USA
  • Superb362 reviews4.7

Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience!....

    Free Cancellation
    Private Tour
    Start From $78.28
 
 

Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

(4.8 of 576 reviews)

-Open bar fully included in $80 ticket: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boarding — no harbor shuttle, no bus, no wasted time -Spacious 45-foot catamaran with near 360 degree view -Families wel... More

Free Cancellation
Private Tour
Start From $84.77
 
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu Likely to Sell Out

Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

  • USA
  • Superb576 reviews4.8

-Open bar fully included in $80 ticket: beer, wine, cocktails, and more -21+ only on Fridays! -Direc....

    Free Cancellation
    Private Tour
    Start From $84.77
 
 

Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

(4.7 of 2,118 reviews)

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More

Free Cancellation
Private Tour
Start From $99.00
 
Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed Likely to Sell Out

Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

  • USA
  • Superb2,118 reviews4.7

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

2-Hour Sunset Sail on the San Francisco Bay

(4.8 of 409 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

  • USA
  • Superb409 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
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 734 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 a... More

Free Cancellation
Private Tour
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • USA
  • Superb734 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $136.19
 
 

Sightseeing Day Sail around Boston Harbor

(4.8 of 560 reviews)

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail past the seaport district, Castle... More

Free Cancellation
Private Tour
Start From $66.54
 
Sightseeing Day Sail around Boston Harbor Likely to Sell Out

Sightseeing Day Sail around Boston Harbor

  • USA
  • Superb560 reviews4.8

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner....

    Free Cancellation
    Private Tour
    Start From $66.54
 
 

Sunset Sail Along the San Diego Skyline

(4.9 of 627 reviews)

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water.  Our San Diego Bay Sunset Sailing Cruises provide an up-close and personal view o... More

Free Cancellation
Private Tour
Start From $99.00
 
Sunset Sail Along the San Diego Skyline Likely to Sell Out

Sunset Sail Along the San Diego Skyline

  • USA
  • Superb627 reviews4.9

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

New York Sunset Schooner Cruise on the Hudson River

(4.9 of 224 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
Private Tour
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

  • USA
  • Superb224 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $90.12
 
 

Key West Sailing & Snorkeling: A Reef Adventure

(4.7 of 219 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 Sailing & Snorkeling: A Reef Adventure Likely to Sell Out

Key West Sailing & Snorkeling: A Reef Adventure

  • USA
  • Superb219 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
 
 

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

(4.9 of 691 reviews)

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk like a pirate then climb aboard the Black Sparrow and set sail in search of treasure! But wait it's no... More

Free Cancellation
Private Tour
Start From $47.99
 
Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger Likely to Sell Out

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

  • USA
  • Superb691 reviews4.9

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos.....

    Free Cancellation
    Private Tour
    Start From $47.99
 
 

Monterey Bay Whale Watching

(4.6 of 330 reviews)

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey Bay Canyon, one of the largest underwater canyons in the wor... More

Free Cancellation
Private Tour
Start From $69.95
 
Monterey Bay Whale Watching Likely to Sell Out

Monterey Bay Whale Watching

  • USA
  • Superb330 reviews4.6

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watchi....

    Free Cancellation
    Private Tour
    Start From $69.95
 
 

Day's End Cocktail Sunset Sail

(4.7 of 84 reviews)

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. This isn’t a dinner cruise, it’s happy hour reimagined (a true ‘pau hana’ at sea) with handcrafted drin... More

Free Cancellation
Private Tour
Start From $159.00
 
Day's End Cocktail Sunset Sail Likely to Sell Out

Day's End Cocktail Sunset Sail

  • USA
  • Superb84 reviews4.7

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....

    Free Cancellation
    Private Tour
    Start From $159.00
 
 

Key West Reef Snorkel & Sail Adventure

(4.7 of 557 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
  • Superb557 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
 
 

Waikoloa Signature Catamaran Sunset Sail

(4.7 of 407 reviews)

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers a smooth, comfortable ride with panoramic views of Mauna Kea... More

Free Cancellation
Private Tour
Start From $159.00
 
Waikoloa Signature Catamaran Sunset Sail Likely to Sell Out

Waikoloa Signature Catamaran Sunset Sail

  • USA
  • Superb407 reviews4.7

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. De....

    Free Cancellation
    Private Tour
    Start From $159.00
 
 

Sunset Sail in Key West with Beverages Included

(4.9 of 956 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
Private Tour
Start From $79.00
 
Sunset Sail in Key West with Beverages Included Likely to Sell Out

Sunset Sail in Key West with Beverages Included

  • USA
  • Superb956 reviews4.9

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

(4.4 of 381 reviews)

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant sailing experience. Guests board a spacious Fury Catamaran, part of the largest luxury fleet in the Florida Keys, and sail to North Ame... More

Free Cancellation
Private Tour
Start From $59.95
 
Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail Likely to Sell Out

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

  • USA
  • Exellent381 reviews4.4

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Day Sails and Sunset tours on Schooner Surprise in Camden Maine

(4.9 of 93 reviews)

Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at most and have cushioned seating on board for all. Experienced crew will point out wild life, tell you history of our area and show... More

Free Cancellation
Private Tour
Start From $73.00
 
Day Sails and Sunset tours on Schooner Surprise in Camden Maine Likely to Sell Out

Day Sails and Sunset tours on Schooner Surprise in Camden Maine

  • USA
  • Superb93 reviews4.9

Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at ....

    Free Cancellation
    Private Tour
    Start From $73.00
 
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