Public vs. Private Sails: Which Experience Is Right for You?
Sailing is one of the best ways to experience Hilton Head Island — but when it comes to booking a sail, one question always comes up: Should you choose a public sail or a private sail? Both offer incredible views, smooth sailing, and unforgettable moments — the difference comes down to how you want to…
Your Guide to Dolphin Watching on Hilton Head Island
Why the Best Views Are From the Water — Especially Aboard Rosé 🐬 Dolphin watching is one of Hilton Head’s most iconic experiences — and for good reason. The island is home to a thriving population of Atlantic bottlenose dolphins, known for their playful behavior, curiosity, and graceful movements through the Lowcountry waterways. Whether you’re…
The Salt Marsh Sailing Experience
Private sails designed for smaller groups and meaningful moments If you’re looking for a more intimate way to explore Hilton Head’s waterways, Salt Marsh Sailing delivers the perfect blend of peace, scenery, and authentic island charm. This 6-passenger private sailboat offers an experience that’s both personal and unforgettable. Every sail with Salt Marsh is completely…
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…