What is the seating like on the boat?

Seating is on deck cushions designed for close-to-water viewing; bring a cushion if you prefer extra padding.

What should I wear aboard the Afternoon Sail?

Wear comfortable, non-slip shoes, layered clothing for breezes, and sun protection including a hat and sunglasses.

Will I get wet on the cruise?

Typically guests stay dry, but wind and spray can produce light dampness—bring a light waterproof layer if concerned.

Are there restrooms on board?

Yes, the vessel has a small head accessed down a set of steps.

Do all ages require a ticket?

Yes, everyone on board must have a ticket; children ages three and up are welcome.

Where and when do I check in?

Boarding begins 30 minutes prior to departure at the Stars & Stripes located on the Harbour Town Pier near 149 Lighthouse Rd.

Sail the Stars & Stripes: Private Afternoon Sail in Hilton Head

On Hilton Head Island’s Harbour Town, the afternoon takes on a maritime pace aboard the Stars & Stripes, the original America's Cup 12‑Metre once skippered by Dennis Conner. Departing from Harbour Town Pier near 149 Lighthouse Rd. Hilton Head Island, SC 29928, this private afternoon sail runs 1.5 hours along the island’s tidal waterways, offering close encounters with Atlantic bottlenose dolphins and wide views of salt marshes, maritime forest, and the red-and-white Harbour Town Lighthouse. The boat itself is historic and hands-on: a 12‑Metre designed for competitive racing but reborn for coastal cruises. Guests can choose to help the crew trim sails and feel the weight of the sheets in their hands, or sink into deck cushions and watch dolphins cavort in the bow wake. The vessel’s low profile keeps the water immediate and intimate; you’ll cruise past oyster beds and shrimp boats, under wide Carolina sky, and through channels where egrets and herons hunt at low tide. This experience stands out because it pairs living sailing history with accessible wildlife viewing. Stars & Stripes brings a competitive pedigree to family-friendly afternoons on the water; that lineage is as much a draw as the island scenery. The natural stage is classic Lowcountry—wide salt marshes carved by tidal creek networks, maritime scrub dotted with live oaks, and the shallow shoals where dolphins hunt. Look for the telltale dorsal fins and foraging patterns at river mouths and inlets. Practical details woven into the narrative: boarding begins 30 minutes before departure at the Harbour Town Pier; the boat has a small head accessed down a flight of steps; walkways are narrow and the vessel is not wheelchair accessible. Bring non‑slip shoes, sun protection, and a light jacket—sea spray and breezes can make late afternoons cool. Beer, wine, and non‑alcoholic beverages are available for purchase aboard. Families find the sail especially rewarding: children ages three and up are welcome, and the crew shares local stories and dolphin facts as part of the cruise. Photographers will appreciate the low angles and fast-moving wildlife; aim for the bow or the starboard rail for the best action shots. Conservation-minded travelers should keep a respectful distance from wildlife and follow crew guidance to minimize disturbance. Whether you want a hands‑on sail or a relaxed viewing cruise, this private afternoon option compresses the best of Hilton Head’s coastal character into 90 minutes—a compact taste of maritime history, active sailing, and wildlife-rich Lowcountry waters. Onboard crew members also point out local landmarks, share navigation anecdotes, and can tailor the pace to quieter observation or more lively sail training for guests seeking a role. They will also advise on tides, ideal photo angles, and local etiquette for wildlife encounters at sea.

About Vagabond Cruise

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.