Personal sail boats

Hilton Head Island Sailing

Whether you’re a family looking for an adventure on the water or a couple wanting a romantic sunset dinner, sailing is one of Hilton Head Island’s favorite pastimes on the water. The breathtaking painted sunsets at dusk, combined with our mild evening weather, make evening sails popular. From private trips and group trips, to dolphin and fireworks outings, you’ll love to set sail in Hilton Head.


Spend a day on a Hilton Head chartered yacht, soaking up the sun in the company of your friends and family. Cruise around the Island and take in the changing scene of the coastline, from impressive waterfront homes to incredible nature preserves. A catered dinner simplifies the experience while you watch the fireworks from the water or host your own special events aboard any one of the chartered yachts available.

Pleasure & Dinner Cruises

Relax and enjoy some of the best local cuisine and vistas from the water aboard any one of our Hilton Head Island pleasure and dinner cruises. You’ll feast on meals catered by some of the area’s favorite restaurants while touring the local waterways and gazing at a beautiful sunset over the Lowcountry. There are also several pleasure cruises available that offer bar services and live music as you cruise the waterways.