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1 hour 30 minutes
Mobile ticket
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 and out of Harbour Town.
Service animals allowed
Public transportation options are available nearby
Travelers should have at least a moderate level of physical fitness
We don't offer any infant rates for this trip as the tickets are a per person rate. All ages will need a ticket.
The seating for this cruise is on cushions on the deck of the boat.
Private charters are available for Stars & Stripes. Please contact Vagabond Cruise if you are interested to learn more about this option.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Harbour Town Lighthouse and Museum
Views of the Harbour Town Lighthouse and Marina where the America's Cup Stars & Stripes departs!
Beautiful low-country views
90-minute Sail aboard the America's Cup - 12 Meter
An opportunity to participate as a crew member
Sea Pines Resort vehicle entry fee
Beverages (soda, water, beer, and wine can be purchased on board)
511 reviews
Total reviews and rating from Viator & Tripadvisor
Lisa W,Mar 26, 2026
- Review from Viator
It was really fun, great experience with Captain Pete and the crew. Great way to see Hilton Head Island from the water. If you never been on large sailboat, this is a must. And we saw dolphins.


Jean K,Mar 23, 2026
- Review from Tripadvisor
Captain Jack and crew were amazing. Although there were a range of ages and groups (couples, bachelorette party, retirees), the crew customized their service to your interest and needs. Highly recommend!

Lilian H,Mar 21, 2026
- Review from Viator
Captain Peter, Ian, and Ella were wonderful! We had an amazing time! The crew was knowledgeable and welcoming.
bxallen,Mar 14, 2026
- Review from Viator
Best done on a warm sunny afternoon with a good wind! Be prepared for an exciting trip when the boat heels. Captain is friendly and engaging and confident sailors can steer the boat under strict supervision. It's a worthwhile trip!
Molly S,Mar 14, 2026
- Review from Viator
We had a wonderful time! Sam, Ella, and Peter were great and very knowledgeable. They did a great job including my 7 and 9 year olds in some of the tasks. We all had a great time!
GoPlaces39596479873,Mar 12, 2026
- Review from Tripadvisor
Highly Recommended Best Cruise we had ever experienced. We chose the 2hr sunset sailing cruise. Best decision we could have made. We had great weather with solid wind. Great sailing experience with an awesome sunset. The Captain was great along with the crew.

Janet N,Mar 11, 2026
- Review from Viator
This was a fun & relaxing excursion on the Stars & Stripes sailboat! The weather was nice and the crew was very friendly. One word of warning, though. There is not much real space to move around once you find a spot to sit on your cushion.
M7090NIrichardb,Jan 18, 2026
- Review from Tripadvisor
Great experience. Everyone who wanted to got a chance to help with sailing the yacht. The wind dropped off significantly for a short time but came back and we had a great sail.
john d,Nov 15, 2025
- Review from Viator
trip was cancelled TWICE! Original date was 11/10 and second cancellation was 11/14. Alternate dolphin cruise offered and declined. Yacht won't sail without a minimum number of paying guests signing on.
Mary A,Nov 2, 2025
- Review from Viator
Super fun time! Skipper and crew were so caring and wanted to make sure you had the best experience.
Operated by Vagabond Cruise