Hilton Head Sailing

Dolphin Day Sail

Put your feet up, grab a cold beer, and learn about the unique Salt Marsh Ecosystem and local history! We’ll cut the engine and let the wind do all of the work! Be sure to keep an eye out for dolphins and birds! On every trip, we provide a cooler with ice and plenty of water to drink. You are welcome to bring any other drinks and snacks you would like. Please make sure your beer is in cans and you have a plastic cup to pour your wine into.

Dolphin Sunset Sail

Enjoy dolphins, birds, ecosystem, and oyster talks. While we can’t guarantee them as they are wild animals, your chances are certainly high! Every trip we offer is capped at 6 passengers public or private. On every trip we provide a cooler with ice and plenty of water to drink. You are welcome to bring any other drinks and snacks you would like. Please make sure your beer is in cans and you have a plastic cup to pour your wine into.

Afternoon Sail

Only on Hilton Head and only in Harbour Town can you sail aboard the real America’s Cup – 12 Meter – Stars & Stripes once skippered by the famous Dennis Connor!

  • Come sail the afternoon away and join the crew as they keep an eye out for the Atlantic bottle-nose dolphin while enjoying the sun and sights of Hilton Head Island's coastal waters.

  • Relax and work on your tan or join in and help the crew sail. This is a great trip for anyone from 3yr-99!

  • Drinks available for purchase on board including beer and wine

  • Please note that the seating for this cruise is on cushions on the deck of the boat

Sunset Sail

Only on Hilton Head and only in Harbour Town can you sail aboard the real America’s Cup – 12 Meter – Stars & Stripes once skippered by the famous Dennis Connor!

  • Come sail away into the sunset and enjoy the breathtaking views of the sun as it slips into the backdrop of Daufuskie Island and the saltwater marshes.

  • This is the perfect way to end a day on Hilton Head Island.

  • It doesn’t matter if you are a novice to the art of sailing or an expert, a trip aboard Stars & Stripes will leave an everlasting memory! This is a great trip for anyone from 3yr-99!

  • Beverages available for purchase including beer & wine

Dolphin Day Sail
★ 4.9 (88) • $349 • 2 Hours • 6 Passenger Max (all ages) • Great for the family!
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Dolphin Sunset Sail
★ 4.9 (88) • $399 • 2.5 Hours • 6 Passenger Max (all ages) • Great for Couples!
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Afternoon Sail
★ 4.7 (4132) • $50 per person • 1.5 Hours • 20 Passenger Max (all ages) • America's Cup Sailing!
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Sunset Sail
★ 4.7 (4132) • $70 per person • 2 Hours • 20 Passenger Max (all ages) • Evenings
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