All Hilton Head Island Cruises
Looking to discover the best of Hilton Head? Join Island Head Sailing and get the most out of your cruising experience. You can choose between our public cruises and our private cruises for your adventures! Book your cruise online today.
- MOST POPULAR
From
$89
Ease into the morning with mimosas, light brunch bites, and ocean breezes aboard Rosé. This sail offers a laid back luxury experience, perfect for slow mornings and stunning views.
- All Ages
- 2 Hours
- Up to 24 Passengers
- All Ages
- 2 Hours
- Up to 24 Passengers
End your day on the water with a front-row seat to the island’s best show. This shared sailing experience is all about laid-back vibes, sunset skies, and unforgettable views.
- All Ages
- 2 Hours
- Up to 24 Passengers
There’s nothing quite like a golden hour sunset on the water. Toast the sunset with a glass of Rosé, light bites, and soak in the warmth as we sail into the most scenic part of the day.
- All Ages
- 2-6 Hours
- Up to 24 Passengers
Book Rosé for a private sail tailored to your group. Whether you’re celebrating a special occasion, or just want some private time with company, this is the ultimate way to experience Hilton Head from the water.
- All Ages
- 1.5 Hours
- Up to 24 Passengers
Every Tuesday night starting June 3rd, set sail for the best seats in the house. Enjoy a relaxing evening on the water that ends with HarbourFest’s famous fireworks lighting up the sky—an unforgettable Hilton Head tradition.
- All Ages
- 1-10 Hours
- Up to 35 Passengers
Step aboard Bonjour, Hilton Head’s newest and most luxurious charter boat, built for unforgettable experiences on the water. This brand-new vessel is perfect for family gatherings, bachelor & bachelorette parties, company outings, private charters, dolphin cruises, and sunset tours.