Water activity

Hilton Head Island: America’s Cup Sailing Yacht Cruise

4.8 / 5

55 reviews

Activity provider: Vagabond Cruise
Water activity

Hilton Head Island: America’s Cup Sailing Yacht Cruise

Activity provider: Vagabond Cruise

From US$ 52.95 per person

Discover a piece of American sailing history with cruise on the 12-meter Stars & Stripes yacht. Board the boat designed and raced by Dennis Conner in the 1980 America’s Cup competition and enjoy an afternoon sail around Hilton Head Island.

About this activity

Free cancellation
Cancel up to 24 hours in advance for a full refund
Reserve now & pay later
Keep your travel plans flexible — book your spot and pay nothing today.
Covid-19 precautions
Special health and safety measures are in place. Check your activity voucher once you book for full details.
Duration 1.5 hours
Check availability to see starting times.
Live tour guide


  • Enjoy a sailing trip on a 12-meter racing yacht
  • Learn how to sail from your experienced crew
  • Keep watch for dolphins and admire the sights
Full description
Step aboard a former America’s Cup sailing yacht for an afternoon cruise. Discover what it takes to sail a racing yacht as you help the crew, or simply sit back and enjoy the ride. See the sights of the Calibogue Sound and learn about the history of these waters. Have your camera ready as you keep an eye out for dolphins. Drinks and merchandise are available for purchase on board.
  • Cruise
  • Sailing instruction
  • Crew
  • Food and drinks
  • Sea Pines Resort vehicle entry fee
  • Gratuities
Not suitable for
  • People with mobility impairments

Select participants and date



Meeting point

Please arrive at the local partner’s office 45 minutes before your cruise departure time for check-in. The office is located just below the Harbour Town Lighthouse. Parking is limited during the afternoon hours, so make sure to arrive early.

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Important information

What to bring

  • Cash

Not allowed

  • Cooler

Know before you go

  • If you are staying outside of the Sea Pines Resort, there is a $9 fee (cash only) per vehicle entering the resort.
  • This pass allows access to the resort for an entire day.
Customer reviews

Overall rating

4.8 /5

based on 55 reviews

Review summary

  • Guide
  • Transportation
  • Value for money

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We booked six of us for the cruise and had a blast! The captain and crew were super friendly and very informative. Our kids (teenager and young adults) took turns steering the boat and helping with sails. We all had a great time! I would 10/10 recommend!

March 24, 2023

Fun to sail on an America’s Cup yacht. The Captain and 2 crew members were great, welcoming & friendly. The Captain was great about taking pictures for us tourists and making sure people got to man the helm if they wanted to. I would happily recommend and go again myself.

March 24, 2023

This was a major hi light of our trip to Hilton Head! Captain Peter and his crew, Luke and Taylor, were amazing! They were all so personable and so interested in ensuring our trip exceeded our expectations. It certainly did! I highly recommend this sail for anyone interested in getting a water view of the island.

March 24, 2023

Product ID: 396149