Hilton Head Island


SAILING WORLDWIDE

5 Best Hilton Head Island Tours Worldwide

The best days on the water.

The 5 most popular hilton head island tours. What each sail costs, how long you are on the water, and which crews run it well.

5 Best Hilton Head Island Tours Worldwide

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger - From Harbour Town Pier to the Ship: Getting There Without Stress
Cruises & Boat Tours, Hilton Head Island, Tour Reviews

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

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1.Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

A 90-minute Black Dagger pirate cruise on Hilton Head with kid pirate gear, a treasure hunt, and a water-cannon battle with Stinky Pete.

Most Popular★ 5.0

“This was a well done family experience, and the crew/staff did a wonderful job. They played their pirate characters, and did great with the kids. Our four year old daughter who is more into princesses than pirates, said it was the best day of her life!”

668 reviews1 hour 30 minutes (approx.)From $47.99by Pirates of Hilton Head

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America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head - The 90-minute itinerary: what you actually do during the sail
Cruises & Boat Tours, Hilton Head Island, Luxury Yacht Trips, Sailing, Tour Reviews

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

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2.America’s Cup 12-Meter Yacht Afternoon Sail from Hilton Head

A 90-minute sail on Hilton Head’s Stars & Stripes 12-Meter. Help raise sails, enjoy Intracoastal views, and cruise small-group.

★ 4.5

“Outstanding! The boat was amazing. We saw more dolphins than we had seen on any previous dolphin tours which was great for the kids on board. Great first mate!! He explained things well and shared his knowledge on the area. It was a really fun afternoon.”

504 reviews1 hour 30 minutes (approx.)From $55.00by Vagabond Cruise

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Parasailing Adventure at the Hilton Head Island - The Boat Setup: Custom Parasail Boat, Back-of-Boat Takeoff
Hilton Head Island, Island-Hopping Sails, Parasailing, Tour Reviews

Parasailing Adventure at the Hilton Head Island

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Hilton Head Island: America’s Cup Afternoon Sail - From Harbour Town Pier to the water: timing, parking, and the Sea Pines factor
Cruises & Boat Tours, Hilton Head Island, Island-Hopping Sails, Tour Reviews

Hilton Head Island: America’s Cup Afternoon Sail

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4.Hilton Head Island: America’s Cup Afternoon Sail

Sail on the real America’s Cup yacht Stars & Stripes from Harbour Town, help trim sails or take the helm, and spot dolphins.

★ 4.8

“I’ve never been on a sailboat before and it was magical to watch the crew set the sails and give us a delightful 2 hours AND a sunset! This boat actually won the America’s Cup years ago. The crew was very friendly—we especially enjoyed hearing stories about the island—the captain (I regret I didn’t catch…”

167 reviews1.5 hoursFrom $55by Vagabond Cruise Hilton Head

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Hilton Head Island: America’s Cup Sailing Yacht Cruise - Checking In at Harbour Town: Pier Timing and Resort Fees
Cruises & Boat Tours, Hilton Head Island, Island-Hopping Sails, Luxury Yacht Trips, Sailing, Tour Reviews

Hilton Head Island: America’s Cup Sailing Yacht Cruise

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5.Hilton Head Island: America’s Cup Sailing Yacht Cruise

Sail on the historic 12-meter Stars & Stripes around Hilton Head’s Calibogue Sound. Learn to sail, steer, and spot dolphins.

★ 4.8

“We had a perfect day- sunny but not too hot- with a nice wind- the captain and crew were so nice! Very informative re the boat and the surrounding islands. I enjoyed chatting with everyone on board. I could have stayed out there twice as long!”

152 reviewsFrom $53by Vagabond Cruise Hilton Head

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