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 got you covered. Our team works closely with you to craft a tailored sailing itinerary that matches your needs, preferences, and desires. The result? A one-of-a-kind day or evening on the water, aboard Rosé, that exceeds your expectations.

A Custom Private Sail with Island Head Sailing is all about flexibility and personalization. Imagine cruising the serene waters of Hilton Head with just your closest friends, family, or colleagues, enjoying a peaceful, personalized adventure. You can expect: tailored itineraries, exclusive experiences, and personalized add-ons. This is your sail, your way. You’ll have the entire boat to yourself, so you can celebrate in complete privacy or invite a select group to share the journey with you..

There’s no better way to experience Hilton Head Island’s stunning waterways than from the comfort of a private sail. Rosé offers a smooth, intimate ride with plenty of space for you and your guests to enjoy. Whether you’re looking for a day of relaxation or an adventure that’s as thrilling as it is beautiful, we’ll work with you to ensure your sail is exactly what you’ve been dreaming of. And with our experienced crew at the helm, you can just sit back, relax, and soak in the stunning views while we take care of the details.

Ready to create your perfect sailing experience?

👉 Book your custom Private Sail now at islandheadsailing.com or 843-6