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Private Sail Aboard America’s Cup Yacht Stars & Stripes

Your Private America’s Cup Sailing Experience on Hilton Head Island

Quick Details

  • Equipment: Clean & Safe
  • Duration: 90 minute afternoon sails (that can be extended by 30 minute increments) or 2 hour sunset sails
  • Vessel: "Stars & Stripes" an authentic America’s Cup racing yacht
  • Departure: Harbour Town, Hilton Head Island
  • Group Size: Private sailboat charters with captain and crew available for groups of 29 or less
  • Food & Drink: Beer, wine, prosecco, cocktails, soft drinks, and catered food packages available after booking
  • Best for: Corporate outings, family gatherings, bachelor and bachelorette parties, celebrations, private events, and sunset sails

Private Afternoon

90-minutes

$ 1,000

Private Sunset

2-hours

$ 1,400

Your Private America’s Cup Sailing Experience on Hilton Head Island

Step aboard Stars & Stripes for a private sailboat charter unlike anything else on Hilton Head Island. This legendary America’s Cup racing yacht gives your group exclusive access to one of the most iconic vessels in Harbour Town, paired with the beauty of the Lowcountry coastline.

Your private sailing yacht charter includes the entire Stars and Stripes sailboat, a professional captain, and an experienced crew to guide your time on the water. Relax as you take in views of Calibogue Sound, Daufuskie Island, Harbour Town Lighthouse, and Hilton Head’s coastal waters, or join the action by helping raise sails, grinding winches, and taking a turn at the helm.

Choose a 90-minute afternoon sail, with the option to add more time in 30-minute increments, or book a 2-hour sunset sail for golden hour views over the water. Food and beverage packages are available after booking, including beer, wine, prosecco, cocktails, soft drinks, and catered options.

Ideal for corporate outings, family gatherings, bachelor and bachelorette parties, celebrations, and private events, this Hilton Head yacht charter brings together hands-on sailing, stunning scenery, and an unforgettable setting aboard the Stars and Stripes boat.

Reserve your private sail aboard Stars & Stripes today and experience Hilton Head from the deck of an authentic America’s Cup yacht.

Highlights of Our Hilton Head Yacht Charter

  • ⛵ Charter the iconic Stars and Stripes sailboat for a private Hilton Head sailing experience
  • 🏆 Enjoy exclusive use of an authentic America’s Cup yacht with your group
  • ⚓ Sail from Harbour Town with a professional captain and crew
  • 🌅 Take in views of Calibogue Sound, Daufuskie Island, Harbour Town Lighthouse, and Hilton Head’s coastline
  • 🤝 Make the experience as relaxed or hands-on as you like, from lounging on deck to helping work the sails
  • 🕒 Choose an afternoon private sailboat charter or a 2-hour sunset sail
  • 🍾 Add food and beverage packages after booking to customize your private event
  • 🎉 Plan a standout Hilton Head yacht charter for celebrations, team outings, family gatherings, or special occasions

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