America's Cup Yacht Sail: Unique Hilton Head Experience

495 Ratings

Hilton Head Island

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Exclusively in Harbour Town, located on Hilton Head, you have the opportunity to sail on the authentic America’s Cup 12-meter vessel, Stars & Stripes, previously commanded by renowned Dennis Connor. All voyages occur entirely under sail, with the engine only being used for departure and arrival in Harbour Town.

Duration: 1 hour, 30 minutes

Cancellation: 24 hours

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Highlights

Harbour Town Lighthouse and Museum - Views of the Harbour Town Lighthouse and Marina where the America’s Cup Stars & Stripes departs!

What's Included

Beautiful low-country views
90-minute Sail aboard the America’s Cup - 12 Meter
An opportunity to participate as a crew member

What's Not Included

Does not include entry into the Sea Pines Resort ($9.00 cash) per vehicle fee
Does not include beverages, available for purchase throughout the sail

Additional Information

We don’t offer any infant rates for this trip as the tickets are a per person rate. All ages will need a ticket.
Stars & Stripes is USCG approved to carry up to 30 passengers, but since COVID we have limited public capacity to 20 passengers.
Private charters are available for Stars & Stripes. Please contact Vagabond Cruise if you are interested to learn more about this option.

Location

149 Lighthouse Rd

Lighthouse Road

Stars & Stripes is located in Harbour Town Yacht Basin just below the lighthouse. Check-in for this sail will be at the Vagabond Cruise reservation office just to the left of the Harbour Town Lighthouse.

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings

4.6

(495 Ratings)

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Christopher_g

Sep 27, 2025

Wonderful trip on the Stars & Stripes - Helpful and accommodating staff people. Perfect trip around the bay that included a number of dolphins rising around the boat. Peter the Captain did a nice job making sure pictures were taken with great backgrounds. Had fun when sails were running full and you could feel what it must have been like to race. Great trip.

Review provided by Viator

Billl643

Sep 26, 2025

An Excellent Sail Boat Adventure - This sail boat ride was one of the highlights of our Hilton Head Island vacation. The crew gets to know their passengers and they also provide some background related to Hilton Head Island which is interesting,

Review provided by Tripadvisor

Cindy_l

Sep 23, 2025

Great sunset cruise! - This sailing experience was awesome. Captain Peter was very experienced and made you feel comfortable. So much knowledge in sailing and the area kept you interested in the experience. My husband was able to steer the Sailboat for an hour, WOW. Highly recommend the trip, the sunset was so beautiful. I suggest sitting in the back vs the cushions up front if you are not flexible.

Review provided by Viator

Frances_a

Sep 20, 2025

My first Sailing - Captain loved ensuring everyone had good time. He voluntered to take pictures. He shared a lot of HH history. Crew was very friendly.

Review provided by Viator

Michael_c

Sep 17, 2025

Awesome sailing experience!! - This was a fantastic experience, and well worth the very reasonable price. My wife and I really enjoyed ourselves and I especially appreciated the opportunity to have a hand helping raising the mainsail and taking a turn at the wheel! The wind wasn't super strong but we still got some good stiff breezes and got some decent heeling going on. The captain knows his stuff and had lots of interesting info and trivia about the boat and the area in general. Also we saw lots of dolphins which was icing on the cake for sure!

Review provided by Viator

Mark_s

Sep 16, 2025

Sailing and sightseeing! - Just a great day on the water with some friendly, knowledgeable people! I would go back in a heartbeat!

Review provided by Viator

Brenda_q

Sep 16, 2025

Relaxing Sail Boat Cruise - A wonderfully relaxing afternoon spent on the Stars & Stripes sailboat. I highly recommend this adventure. Staff was so polite and attentive! Great way to spend an hour & a half of your day

Review provided by Viator

Anita_r

Sep 13, 2025

Absolutely lovely experience - Absolutely lovely experience!  Last summer, I cruised with my family and we had a blast—so much so that I booked it again this year when I brought some friends to the island. We all thoroughly enjoyed the cruise and the wonderful crew. Both Ian and Claudine were incredibly friendly and helpful throughout the trip. And Captain Peter? He’s an absolute rockstar! He shared fascinating facts about the island, patiently answered all our questions, and made sure everyone got great photos on their phones. He truly went above and beyond to make it special. Thanks for the memories!

Review provided by Viator

Patricia_o

Sep 12, 2025

Peter was an excellent... - Peter was an excellent captain who encouraged those passengers familiar with sailing to assist in many ways. Seating and movement around boat challenging for anyone with any physical issues but captain tries to accommodate as much as possible. Very beautiful sail and afternoon!

Review provided by Viator

Terriwaring