Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by the famous Dennis Connor. All trips take place under full sail. We only use our motor to get in a... More

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk like a pirate then climb aboard the Black Dagger and set sail in search of treasure! But wait it's not... More

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island - generally best conditions for sailing). During Sunset, This is generally still pretty breezy with some goo... More

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the North side of the island. During the day, this is generally filled with exciting winds for gre... More

Set sail into the sunset aboard Rosé, our 36-foot luxury sailing catamaran. This 2-hour sunset cruise offers panoramic views of the Hilton Head coastline with complimentary drinks on board. Whether you're going with a big or smal... More

This 2-hour daytime sail offers a smooth, spacious ride through the scenic Calibogue Sound with expert captains leading the way. Keep an eye out for dolphins, seabirds, and Lowcountry landmarks as you relax, unwind, and enjoy the ... More

This 2 hour Private Morning Sailing tour, the Captain will take you to Port Royal Sound (North side of the island - generally best conditions for sailing). During the MORNING, this is generally a calm - light wind relaxing sail, a... More

Step aboard Bonjour for a one of a kind dinner cruise where Southern flavor meets coastal charm. Feast on a hearty Lowcountry Boil—piled high with fresh shrimp, sausage, corn, and potatoes—all while cruising the scenic waters ... More

Wake up with our daily Brunch Under Sail aboard a luxury catamaran. Cruise through the calm morning waters of Hilton Head while enjoying complimentary mimosas and light brunch bites. This relaxing 2-hour sail is the perfect blend ... More