Step aboard the Stars & Stripes, a legendary 12 Meter America's Cup yacht, for an unforgettable 1.5-hour afternoon sail on Hilton Head Island. Experience hands-on sailing, coastal views, and dolphin sightings in the heart of South Carolina’s Lowcountry.
Step aboard the Stars & Stripes, a legendary 12 Meter America's Cup yacht, for an unforgettable 1.5-hour afternoon sail on Hilton Head Island. Experience hands-on sailing, coastal views, and dolphin sightings in the heart of South Carolina’s Lowcountry.
Book with Vagabond Cruise
Verified experiences and guided adventures in the surrounding area.
Operated by Vagabond Cruise · Hilton Head Island, South Carolina
easy.
1.5 hours.
Suitable for most fitness levels as sail participation is optional and seating is available for relaxation.
Yes, the minimum age is 3 years old, and everyone requires a ticket regardless of age.
Usually guests remain dry, but occasional sea spray might cause light dampness, so bring a waterproof layer if desired.
Yes, there is a small restroom located on the boat, accessible via a few steps.
Absolutely, guests are welcome to join the crew and help with sailing tasks during the trip.
Boarding is at Harbour Town Pier, 149 Lighthouse Rd., Hilton Head Island, SC.
No, the boat has steps and narrow walkways which can limit accessibility; notify the crew in advance for assistance.
Stars & Stripes is a historic 12 Meter yacht that raced for the America’s Cup in 1987 under skipper Dennis Conner, a legend in competitive sailing.
Efforts are in place to minimize environmental impact during sailing with strict waste regulations and education on marine ecosystem preservation.
Vagabond Cruise operates a diverse fleet from Hilton Head Island, offering narrated wildlife excursions, specialty dining cruises, private charters, and seasonal holiday sailings. Flagship vessels include the Tammy Jane, Spirit of Harbour Town, Solaris, Vagabond, and the historic Stars & Stripes, each tailored for experiences ranging from two-hour crabbing and shrimping expeditions to multi-hour trips to Daufuskie Island and Savannah. Guests can choose guaranteed dolphin encounters on ocean and estuary cruises, relaxed sandbar sunbathing charters, intimate Solaris private charters for up to ten guests, or festive themed sailings such as fireworks dinners, holiday brunches, and the Gregg Russell Bubble Gum Cruise. Dining options feature Lowcountry menus and plated dinners crafted by award-winning chefs, buffet brunches, and specialty Gullah Geechee cuisine, with indoor climate-controlled cabins and open-air decks available. Educational offerings include narrated naturalist sunset dolphin cruises, stargazing sessions with “Bill the Sky Guy,” and paranormal ghost tours led by local experts. The company highlights hands-on marine experiences—baiting crab pots, hauling shrimp nets, and sorting fresh Carolina shrimp—designed for families and curious travelers. Safety and professional service are provided by experienced captains and trained crew, with full-service bars and private tables on select vessels. Vagabond Cruise partners with Sea Pines Resort for catering on exclusive Solaris charters and coordinates holiday events throughout the season. With a broad calendar of daily and special-event sailings, Vagabond Cruise delivers reliable, locally rooted maritime adventures across the Lowcountry. Bookings are available online with flexible options for groups, families, and private celebrations and seasonal themed departures.
Book with Vagabond Cruise