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Hilton Head Island Sailing & Cruises


Whether you're a family looking for an adventure on the water or a couple wanting a romantic sunset dinner, sailing is one of Hilton Head Island's favorite pastimes on the water. The breathtaking painted sunsets at dusk combined with the mild evening weather, make evening sails popular. Enjoy a variety of sailing excursions, from private trips and group trips, to dolphin and fireworks outings.


Spend a day on a chartered yacht, soaking up the sun in the company of your friends and family. Take a cruise around the Island and enjoy the changing scene of the coastline, from impressive waterfront homes to incredible nature preserves. A catered dinner simplifies the experience while you watch the fireworks from the water or host your special events aboard any one of the chartered yachts available.

Pleasure & Dinner Cruises

Relax and enjoy some of the best Island cuisine and vistas from the water aboard any one of the pleasure and dinner cruises. You'll feast on meals catered by some of the area's favorite restaurants while touring the local waterways and taking in the beautiful sunset over the Lowcountry. If you're not interested in dining, there are several cruises that offer bar services and live music as you cruise the waterways.

Listings for Sailing, Yachting & Cruises

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Advanced Sail, Inc. Catamarans

Advanced Sail, Inc. Catamarans

The "Environmentally Friendly Way" to enjoy nature under sail. Whether it's daytime cruising, dolphin watching, sailing lessons, taking in a fabulous sunset or enjoying fireworks, Pau Hana and Flying Circus are FUN for all ages. Both boats are extremely....Read More

T: (843) 686-2582View Website

Address: 86 Helmsman Way, Hilton Head Island, SC 29928

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Commander Zodiac, Inc.

Commander Zodiac, Inc.

It's always a beautiful day at South Beach Marina! Come join us for your family adventure. Explore the wonderous waters of the low country on an amazing Dolphin excursion or sail along with playful dolphins in your wake. The kids will love our mornings....Read More

T: (843) 671-3344View Website

Address: 232 S. Sea Pines Drive, Hilton Head Island, SC 29928

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H2O Sports

H2O Sports

H2O Sports, located at the Harbour Town Yacht Basin/The Sea Pines Resort, offers water fun for all ages.

All of our Captains are USCG licensed and trained specifically in the area they work. You know you're getting the best and most current equipment....Read More

T: (843) 671-4386View Website

Address: 149 Lighthouse Rd., Hilton Head Island, SC 29928

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Pirates of Hilton Head LLC

Pirates of Hilton Head LLC

Bring your little pirate aboard the Black Dagger and set sail on the pirate cruise of their dreams! From Beginning to end the action is non-stop as we transform the kids into our Pirate Crew. The adventure starts at the dock where each little mate gets....Read More

T: (843) 363-7000View Website

Address: 149 Lighthouse Road, Hilton Head Island, SC 29928

Contact Us
1 Chamber of Commerce Drive
PO Box 5647
Hilton Head Island, SC 29938

Toll-Free in US: 800-523-3373

Hilton Head Island Visitor & Convention Bureau