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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.
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)
For a full refund, cancel at least 24 hours before the scheduled departure time.
540 reviews
Total reviews and rating from Viator & Tripadvisor
teapot-texan,Jun 20, 2026
- Review from Tripadvisor
Understand that the charter can’t control the wind but on windless days operator could do a bit more help or even just apologize for a one and a half hour trip in near windless conditions. Captain and crew were good. Just feel like the operator only watch for foul weather. This not a comfortable boat when the midday sun is brutal.

MichaelC L,Jun 19, 2026
- Review from Viator
Sailing an America’s Cup 12 meter is a rare opportunity. Stars & Stripes was significant to the USA recapturing the America Cup. Captain Pete is s legend and fun host allowing passengers to help raise sails and take the helm or just sit back and enjoy a beautiful sail. The crew of young ladies were welcoming, friendly, attentive and amazing at hoisting and trimming sails. A truly wonderful family experience.
K7833FOtimothyw,Jun 19, 2026
- Review from Tripadvisor
Trip was cut short due to weather, but otherwise was very good experience. The charter company did issue a partial refund due to lack of a full scheduled outing.
578sds,Jun 17, 2026
- Review from Tripadvisor
A must when on Hilton Head Island. Captain Peter was a delight and eager to let guests experience the helm of this classic 12 meter. The crew of three capable young ladies were welcoming, friendly and amazing to watch as they raised and trimmed sails. You can enjoy a wonderful sail while relaxing or jump in to help crew. A great family event.
Anonymous,Jun 12, 2026
- Review from Viator
Come very early to get a good seat is yiu are over 80. Folks that have extensive sailing experience might get a chance to stear the boat for a while.
L3331LHCLovern,Jun 11, 2026
- Review from Tripadvisor
Wonderful experience on the sailboat. The crew was very personable and welcoming! Beautiful views of Hilton Head, dolphins and a sunset. The crew encouraged participation and were fun to be around.

Terrie A,Jun 4, 2026
- Review from Tripadvisor
Enjoyed the sail boat trip, staff was amazing! No problem with booking!! Would definitely recommend



Tonya S,Jun 2, 2026
- Review from Tripadvisor
Captain and Crew were fantastic! Personable and fun experience for all ages.
Brad B,May 19, 2026
- Review from Viator
Peter and his first mates were very helpful and knowledgeable about the history of the boat, the area and wildlife. Very accommodating...we had someone in our group w a bad back and they loaded her first and gave her a spot she was comfortable in for the entire hour and a half.
miamT6423XV,May 15, 2026
- Review from Tripadvisor
Wonderful experience! The crew was friendly and super knowledgeable, pricing is super affordable, and boat is gorgeous. Absolutely would go every time I visit Hilton Head!


Operated by Vagabond Cruise