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    1. Local experiences
    2. /Things to do in Hilton Head Island…
    3. /Water Activities
    4. /Sailing
    5. /Hilton Head America's Cup Sailing Cruise
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    Hilton Head America's Cup Sailing Cruise

    Charter Stars and Stripes for a private 1.5-hour afternoon sail

    4.8 stars• 7.9K reviews
    From$1,177incl. taxes and fees

    Duration

    1.5 hrs

    Ideal For

    Up to 29 people

    Includes

    Crew participation, sailing cruise

    Highlights

    Sail Hilton Head Island's coastal waters aboard the 12 Meter Stars and Stripes, once skippered by Dennis Conner. Charter this private afternoon sail for up to 29 guests and choose to help sail or relax on deck.
    • Charter Stars and Stripes for up to 29 guests
    • Help the crew sail or relax on deck cushions
    • Take in coastal views from Harbour Town
    • Watch for Atlantic bottlenose dolphins with the crew
    • Purchase beer, wine, prosecco, soda, and water on board

    Know before you go

    • Arrive 45 minutes before departure; boarding begins 30 minutes before departure
    • Pay a $10 entry fee per vehicle when entering Sea Pines Resort from outside the resort
    • Meet at 149 Lighthouse Rd., Hilton Head Island, SC 29928
    • Expect deck-cushion seating, steps to board, and narrow walkways around the boat
    • Note that Stars and Stripes is not wheelchair accessible
    • Plan for every guest, regardless of age, to have a ticket

    Cancellation Policy

    Full refund with at least 48 hours' cancellation notice. No-shows are charged the full price. Full refund if the operator cancels due to weather or other unforeseen circumstances. If the minimum passenger count is not met, choose another cruise or receive a full refund.

    FAQs

    Wear comfortable clothing and non-slip shoes; avoid heels. Bring a light jacket or sweater for cooler breezes, plus sunscreen, a hat, and sunglasses for sunny conditions.

    Guests typically stay dry, but wind conditions and sea spray can make you a little damp. Bring a light jacket or waterproof layer if you prefer.

    Yes. Stars and Stripes has a small restroom, called a head, down a set of steps.

    Meeting details

    Stars and Stripes, Harbour Town Pier

    Experience provided by Vagabond Cruise
    Experience provided by Vagabond Cruise

    Related locations

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Reference #G627NN

    Private Sail

    $1,177

    For 29 passengers or less | Includes taxes and service charge.

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

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      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.8
    Excellent
    7.9K reviews•Google Maps
    6,631
    727
    204
    76
    103

    This cruise operation clearly has its act together when it comes to hospitality and wildlife viewing. The crew stands out as a major highlight across the board, with multiple guests praising Captain Windows and Captain Peter by name for their warmth, knowledge, and genuine passion for what they do. Whether you're on the Dolphins and Donuts morning cruise, a sunset dinner sail, or one of their day trips to Savannah or Daufuskie Island, the staff consistently checks in on passengers and creates a welcoming atmosphere. Dolphin sightings are practically guaranteed, with some groups spotting over 20, and the crew takes time to educate guests about the marine life while ensuring everyone gets good photo opportunities. The food on dinner cruises gets mixed feedback. Most guests are pleasantly surprised by how good the salads and desserts are, but one detailed review noted that all the protein options came out dry and disappointing. The bigger consistent complaint involves comfort, specifically the heat and lack of adequate shading while the boat is docked or during sunny portions of the journey. Missing or insufficient window shades became an issue for multiple passengers. Drink prices also raised some eyebrows. Still, the overall experience seems to win people over, especially families and repeat customers who return year after year for specific routes. Just book early if you're eyeing that afternoon Daufuskie trip, as it fills up fast.

    What people are saying

    Review 1 of 4
    5/5

    This was our 2nd cruise with Vagabond. We did the dinner cruise on our last visit and it was awesome. Our sunset dolphin cruse with Captain Mike was everything promised and then some. We got to see dolphins in their natural habitat and the sunset was spectacular. The narrative provided was funny, entertaining and informative. What more could you ask? Would do it again.

    Photo of Joyce Williams

    Joyce Williams

    July 7, 2026

    Review 1 of 1
    5/5

    This was our 2nd cruise with Vagabond. We did the dinner cruise on our last visit and it was awesome. Our sunset dolphin cruse with Captain Mike was everything promised and then some. We got to see dolphins in their natural habitat and the sunset was spectacular. The narrative provided was funny, entertaining and informative. What more could you ask? Would do it again.

    Photo of Joyce Williams

    Joyce Williams

    July 7, 2026

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