Island Head Sailing

Island Head Sailing offers Hilton Head Island’s most memorable sailing experiences aboard Rosé, our 24-passenger luxury catamaran. This sailboat  sets the stage for something truly special on the water. Set sail during our signature Golden Hour Sunset Sail, indulge in Brunch Under Sail, or enjoy the sea your way with private and public day and sunset charters. Whether you’re celebrating, reconnecting, or simply soaking in island life, every sail is crafted for connection, comfort, and stunning Lowcountry scenery. Departing from the heart of Hilton Head, Island Head Sailing turns ordinary outings into extraordinary experiences.