The Perfect Day on the Water, Designed Just for You
At Island Head Sailing, we believe every adventure on the water should be as unique as the people aboard. That’s why we offer customizable Private Sails—an exclusive opportunity to design your own perfect sailing experience on Hilton Head Island. Whether you’re celebrating a milestone, hosting a corporate event, or just seeking an intimate escape, we’ve…
From Sun to Sunset: Your Ultimate Sailing Trip
Whether you’re soaking up the sun on a daytime ride or catching the colors of a Lowcountry sunset, a Public Sail with Island Head Sailing is the ideal way to experience Hilton Head from the water. Daytime Sail The public Day Sail offers a perfect escape to unwind and enjoy Hilton Head’s calm waters during…
Toast the Coast at Sunset
There’s something magical about Hilton Head at sunset—and the best way to take it all in? Aboard Rosé, our luxury sailing catamaran, during the most photogenic hour of the day. The Golden Hour Sail is a dreamy, evening escape designed for laid-back luxury. As the sun begins its descent, we set sail into calm Lowcountry…
Brunch with a Breeze
There’s brunch… and then there’s Brunch Under Sail. Skip the waitlists and crowded restaurants—this is Hilton Head brunch reimagined. Aboard our signature luxury sailing catamaran Rosé, you’ll start your day with fresh ocean air, panoramic views of the Lowcountry, and a laid-back atmosphere that’s perfect for relaxing, celebrating, or simply soaking in the beauty of…