Best results for Sailing in Hilton Head Island, SC

Set sail on a private Hilton Head outing for up to six guests

Sail privately for 2–6 hours with up to six guests

Spend two hours sailing from Broad Creek Marina

Sail a spacious catamaran as the day winds down over Hilton Head waters

Sail Lowcountry waterways with brunch and included drinks

Sail into the sunset with space for up to 35 guests

Private 2-hour sail to learn the salt marsh and watch for dolphins

Sail at sunset with your group and watch for dolphins

Watch Hilton Head's vibrant sunset while relaxing or helping crew aboard the historic Stars & Stripes

Join the crew or relax on a 1.5-hour Hilton Head coastal sail aboard a historic America’s Cup yacht

Private captained sail on Calibogue Sound with room for your snacks and drinks

Sail Hilton Head’s coast aboard the historic Stars & Stripes

Sail the historic Stars & Stripes into a Hilton Head sunset

Take the helm on a private, wind-powered afternoon sail for up to six guests

Take the helm or relax on a private afternoon sail for up to 12 guests

Sail Hilton Head’s waterways privately and look for dolphins and coastal birds

Sail Hilton Head’s waterways on a private 2-hour morning cruise for up to 6 guests

Share a small-group afternoon sail and take the helm if you choose

Sail into sunset views on a private charter for your group

Take the helm or relax on a 2-hour public afternoon sail

Choose your own four-hour sail, from ocean cruising to a swim stop

Customize a private afternoon sail for up to six guests

Tailor a four-hour sail with ocean cruising or a swim stop

Sail Low Country waterways on a private charter for up to six guests