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Experience a 90-minute sail on the historic America's Cup 12-Meter yacht from Hilton Head, with scenic views, crew participation, and dolphin sightings.

Aiming to combine history, scenic beauty, and a hands-on sailing experience, the America’s Cup 12-Meter Yacht Afternoon Sail offers an engaging outing from Hilton Head Island for just $52.95 per person. This 1 hour and 30 minutes cruise departs from 149 Lighthouse Rd and features a vessel with an impressive history—a 39-foot sailboat that competed in the America’s Cup.
This tour is perfect for those wanting a relaxing, scenic escape on the water, with views of Harbour Town Lighthouse and Intracoastal Waterway. The trip includes the chance to participate as a crew member, sail the historic boat, and enjoy lowcountry scenery without the noise of motors. While beverages are available for purchase and entry into Sea Pines Resort incurs a $9 fee, the overall experience is praised for its friendly crew and beautiful vistas.

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This sail begins at 149 Lighthouse Rd in Hilton Head Island, a convenient location accessible by public transportation. The meeting point is straightforward to find, and the tour concludes at the same spot. The maximum group size is 20 guests, ensuring a comfortably intimate experience.
Since the vessel is USCG approved, safety is a priority, and Captain Pete along with crew members Callie and Kelly are noted for their friendly, professional approach. Travelers should have a moderate physical fitness level to fully enjoy the hands-on elements, such as helping with sails and steering.
The cruise includes a 90-minute sail on the historic America’s Cup boat, which is vessel Stars & Stripes. Guests get the chance to participate directly as crew members, steering and handling sails, which adds an exciting, interactive element. Low-country scenery and wildlife, like dolphins, manta rays, and pelicans, also provide entertainment during the trip.
Beautiful views of the Harbour Town Lighthouse and the marina where the Stars & Stripes departs are highlights. This offers a rare chance to see Hilton Head’s coastline from the water on a vessel with notable sailing history.

The America’s Cup boat carries a rich history, being a 12-meter yacht that has competed at the highest levels of sailing. Its USCG approval means safety standards are high, but the limited capacity after COVID ensures more space and comfort for guests.
The crew is frequently praised for being informative, friendly, and engaging. They often share local history, making the trip educational as well as scenic. Guests are encouraged to help with the sails and even steer the boat, creating a participatory atmosphere that enhances the overall enjoyment.

Throughout the sail, you can expect beautiful views of Lowcountry landscapes, including marshes, waterways, and skyline. The likelihood of dolphin sightings is high, with many reviews mentioning dolphins as entertainment during the cruise. Birdlife, such as pelicans, adds to the lively and picturesque environment.
The harbor scenery, especially near the Harbour Town Lighthouse, provides iconic photo opportunities. The calm waters and gentle breezes make this a peaceful outing that also offers moments of exhilaration when the sails are hoisted.
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The tour starts at 149 Lighthouse Rd, a well-known spot close to public transportation options. The return is to the same location, making logistics simple for guests. The minimum capacity of the vessel allows for a more personalized experience, with crew members giving personalized attention.
For those interested in private charters, the Stars & Stripes can be booked exclusively through Vagabond Cruise. This option is ideal for special occasions or groups seeking a more customized experience.

Guests should have a moderate physical fitness level to comfortably participate in sailing activities. The vessel has no restroom facilities onboard, so plan accordingly. Service animals are permitted, and the tour is near public transit, easing access for most visitors.
Since the vessel does not include entry into the Sea Pines Resort (which requires a $9 cash per vehicle fee), guests should plan for this additional cost if they wish to visit the resort after sailing.

The sail is weather-dependent; if conditions are unsuitable, the tour is rescheduled or fully refunded. Free cancellation is available up to 24 hours in advance, giving flexibility in planning. If canceled less than 24 hours before, no refund is issued.
The crew readily adapts to changing weather conditions, often adjusting the sailing route to ensure safety and maximum enjoyment. The experience is best on mild, breezy days, which often produce spectacular sailing conditions.
The America’s Cup 12-Meter Yacht Afternoon Sail offers a rare opportunity to experience Hilton Head’s waters aboard a historically significant vessel. The combination of scenic beauty, wildlife sightings, and hands-on participation distinguishes this tour from more passive boat rides.
The knowledgeable, friendly crew, led by Captain Pete, ensures guests feel safe and engaged throughout the cruise. The price point and limited group size make it an excellent value for those wanting a personalized, scenic, and educational sailing experience.
This sail on the historic Stars & Stripes is ideal for adventure-seekers and history enthusiasts alike, offering a relaxing yet engaging outing on Hilton Head’s waters. It suits families, couples, and groups seeking scenic views with opportunities for hands-on sailing.
While the lack of restroom facilities and the simple onboard amenities mean it’s not suited for those seeking luxury or extensive facilities, the scenic beauty and knowledgeable crew compensate well. The chance to sail a vessel with a notable sailing pedigree is a highlight that makes this trip truly special.
For anyone interested in experiencing Hilton Head from the water in a relaxed, interactive way, this America’s Cup yacht cruise offers genuine value and memorable moments.
“Beautiful glide through the sound . Charming Attentive young men for a crew and delightful Captain. A great way to view to Harbor. Being on the wat…”
Is there a minimum age requirement for the cruise?
The data does not specify age restrictions, but guests should have a moderate physical fitness level to enjoy the sailing activities.
Can I participate in steering the boat?
Yes, guests are encouraged to help with sails and steering, making the experience interactive and fun.
Are beverages included?
No, beverages are available for purchase onboard, so bring your own if desired.
What should I wear for the cruise?
Casual, comfortable clothing suitable for sailing and outdoor weather is recommended. Bring sunglasses and sunscreen for protection.
Is there a restroom onboard?
No, the vessel does not have restroom facilities, so plan accordingly.
Can I cancel the booking?
Yes, free cancellation is available up to 24 hours before the trip. Cancellations within 24 hours are not refundable.
Is the tour suitable for children?
The tour is generally suitable for most ages, but guests should be comfortable with standing and moving around on deck.
Are private charters available?
Yes, private charters of the Stars & Stripes are possible through Vagabond Cruise; contact them for more details.
How many passengers can the boat carry?
While USCG approved for up to 30, the public capacity for this tour is limited to 20 for safety and comfort.
What is the main highlight of this tour?
The historic America’s Cup vessel, combined with scenic views and crew participation, provides a unique, engaging sailing experience that stands out from typical boat rides.