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Stop and Smell the Rosé – On the Water!

People boarding a catamaran at a dock on a sunny day.

There’s something special about life on the water — the way the breeze hits just right, the sound of the sails, and the sight of Hilton Head glowing in the sun. On Rosé, Island Head Sailing captures that magic every single day.

Whether you’re planning a laid-back morning, a perfect sunset celebration, or a private sail with your favorite people, Rosé sets the scene for unforgettable moments.

Brunch Under Sail

Start your day the best way — mimosas in hand, the ocean as your backdrop, and the Lowcountry sun rising over the water. Our Brunch Under Sail offers the perfect mix of relaxation and luxury, complete with brunch bites, drinks, and smooth sailing along Hilton Head’s coastline. It’s an ideal way to celebrate a special occasion or simply treat yourself to a morning that feels like vacation.

Golden Hour Sunset Sails

When the day winds down, the sky comes alive — and Rosé is the best seat in the house.
Our Golden Hour Sunset Sail captures Hilton Head’s most stunning view: the warm glow of the setting sun reflecting off the water as the sails fill with a soft evening breeze. Enjoy complimentary drinks to sip, unwind, and toast to the perfect end to your island day.

Day Sails

Experience the island from a whole new perspective.
Our Day Sails are a local favorite — a chance to soak up the sun, spot dolphins, and enjoy Hilton Head’s coastal beauty in full daylight. Whether you’re visiting for the weekend or looking for a mid-day escape, Rosé delivers the perfect blend of adventure and ease.

Private Charters for Any Occasion

Looking for something custom? Every sail on Rosé can be made private for your group. With space for up to 24 guests, it’s perfect for birthdays, anniversaries, bachelor and bachelorette parties, or any reason to celebrate.
Bring your crew, your favorite playlist, and let our team handle the rest — we’ll make sure your time on the water is effortless, memorable, and tailored to your style.

Your Island Head Sailing Experience

Every trip is designed to help you slow down, connect, and enjoy the best of Hilton Head from the water.

Ready to set sail?

👉 Visit islandheadsailing.com or call 843-686-4386 to book your sail on Rosé today.

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