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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.
8,296 ratings
Operated by Vagabond Cruise · Hilton Head Island, South Carolina
Hilton Head Island, South Carolina, offers an exceptional coastal escape where sun, salt, and sea meet history and adventure. One of its most captivating experiences is hopping aboard the Stars & Stripes, a genuine 12 Meter racing yacht that once competed for the America’s Cup under the command of Dennis Conner. This iconic vessel invites you to spend the afternoon sailing the serene waters of Harbour Town, blending thrilling nautical heritage with the natural beauty of the Lowcountry coastline.
The Afternoon Sail isn’t just a cruise; it’s an invitation to participate. Guests can choose to join the crew, learning hands-on sailing techniques, or simply relax on cushions set out on the deck, soaking in panoramic views of the glittering ocean and sweeping island shores. The Stars & Stripes offers an intimate maritime experience, with seating close to the water that lets you feel the spray and hear the wind whisper through the rigging.
As the boat cuts through the gentle waves, keep an eye out for Atlantic bottlenose dolphins, frequently spotted dancing alongside the bow. The crew shares local lore and fascinating facts about Hilton Head’s maritime history, enriching the voyage with a true sense of place. Beverages, including beer and wine, are available on board, making this a perfect afternoon for couples, families, or solo adventurers seeking tranquil excitement.
Boarding takes place at Harbour Town Pier on Lighthouse Road, a central hub of Hilton Head’s outdoor activities. While this sail is welcoming to guests ages three and up, it’s important to note the boat has steps and narrow walkways, so mobility considerations should be addressed in advance. The experience lasts about 1.5 hours, ideal for fitting an authentic sailing adventure into any Lowcountry itinerary.
Hilton Head’s geography, characterized by sandy shores, maritime forests, and a rich estuarine ecosystem, underpins the thrill of this outing. The Stars & Stripes perfectly complements the island’s outdoor recreation scene, offering a unique connection to America’s Cup history rarely available outside specialized sailing communities.
Whether you seek the splash of ocean spray while handling the sails or prefer to unwind with coastal vistas and dolphin sightings, the Afternoon Sail aboard Stars & Stripes serves up a memorable blend of heritage, natural beauty, and peaceful adventure on America’s southeastern coast.
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.
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