Menu

Top 10 Best Hilton Head Island Sailing Trips

Found 7 Sailing Trips activities in Hilton Head Island. Sort by Popularity.
 

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

(4.6 of 436 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

Free Cancellation
Start From $52.95
 
America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head Likely to Sell Out

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

  • Hilton Head Island
  • Superb436 reviews4.6

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

    Free Cancellation
    Start From $52.95
 
 

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

(4.9 of 638 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 Dagger and set sail in search of treasure! But wait it's not... More

Free Cancellation
Start From $41.99
 
Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger Likely to Sell Out

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

  • Hilton Head Island
  • Superb638 reviews4.9

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

    Free Cancellation
    Start From $41.99
 
 

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

(4.9 of 113 reviews)

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the North side of the island. During the day, this is generally filled with exciting winds for gre... More

Free Cancellation
Private Tour
Start From $475.00
 
2-Hour Private Hilton Head Afternoon Dolphin Watching Sail Likely to Sell Out

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

  • Hilton Head Island
  • Superb113 reviews4.9

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind....

    Free Cancellation
    Private Tour
    Start From $475.00
 
 

2 Hour Rosé Luxury Day Sail

(4.9 of 113 reviews)

This 2-hour daytime sail offers a smooth, spacious ride through the scenic Calibogue Sound with expert captains leading the way. Keep an eye out for dolphins, seabirds, and Lowcountry landmarks as you relax, unwind, and enjoy the ... More

Free Cancellation
Private Tour
Start From $74.97
 
2 Hour Rosé Luxury Day Sail Likely to Sell Out

2 Hour Rosé Luxury Day Sail

  • Hilton Head Island
  • Superb113 reviews4.9

This 2-hour daytime sail offers a smooth, spacious ride through the scenic Calibogue Sound with expe....

    Free Cancellation
    Private Tour
    Start From $74.97
 
 

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

(5 of 113 reviews)

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island - generally best conditions for sailing). During Sunset, This is generally still pretty breezy with some goo... More

Free Cancellation
Private Tour
Start From $515.00
 
Private Hilton Head Sunset Sailing Tour with Dolphin Watching Likely to Sell Out

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

  • Hilton Head Island
  • Superb113 reviews5

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound ....

    Free Cancellation
    Private Tour
    Start From $515.00
 
 

Rosé Brunch Under Sail

(5 of 113 reviews)

Wake up with our daily Brunch Under Sail aboard a luxury catamaran. Cruise through the calm morning waters of Hilton Head while enjoying complimentary mimosas and light brunch bites. This relaxing 2-hour sail is the perfect blend ... More

Free Cancellation
Private Tour
Start From $95.23
 
Rosé Brunch Under Sail Likely to Sell Out

Rosé Brunch Under Sail

  • Hilton Head Island
  • Superb113 reviews5

Wake up with our daily Brunch Under Sail aboard a luxury catamaran. Cruise through the calm morning ....

    Free Cancellation
    Private Tour
    Start From $95.23
 
 

Rose Golden Hour Sunset Sail

(5 of 113 reviews)

Set sail into the sunset aboard Rosé, our 36-foot luxury sailing catamaran. This 2-hour sunset cruise offers panoramic views of the Hilton Head coastline with complimentary light bites and drinks on board. Whether you're going wi... More

Free Cancellation
Private Tour
Start From $105.93
 
Rose Golden Hour Sunset Sail Likely to Sell Out

Rose Golden Hour Sunset Sail

  • Hilton Head Island
  • Superb113 reviews5

Set sail into the sunset aboard Rosé, our 36-foot luxury sailing catamaran. This 2-hour sunset crui....

    Free Cancellation
    Private Tour
    Start From $105.93
 
Booking.com
Booking.com
Booking.com