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    1. Local experiences/
    2. Hilton Head Island, SC/
    3. Water Activities/
    4. Sailing/
    5. Hilton Head Sailing on Historic America's Cup Yacht
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    Hilton Head Sailing on Historic America's Cup Yacht

    Join the crew or relax on a 1.5-hour Hilton Head coastal sail aboard a historic America’s Cup yacht

    From$49/ person

    Duration

    1.5 hrs

    Includes

    1.5-hr sail, Crew help, Drinks

    Highlights

    Experience an iconic America’s Cup yacht on a relaxed 1.5-hour afternoon sail along Hilton Head Island’s sparkling coastline. Join the crew or stretch out on deck cushions while sea breezes and scenic views surround you.

    1. Set sail on the 12-meter Stars & Stripes America’s Cup yacht
    2. Watch for Atlantic bottlenose dolphins in their natural habitat
    3. Choose to crew, trim sails, or simply lounge on deck cushions
    4. Purchase beer, wine and soft drinks from the onboard bar
    5. Capture memorable photos of Harbour Town and its lighthouse

    What's Included

    1. 1.5-hour sail aboard Stars & Stripes
    2. Opportunity to assist the crew
    3. Cushioned deck seating

    Things to know

    The vessel is not wheelchair accessible and boarding requires steps and narrow walkways; seating is on deck cushions.


    FAQs

    Q: Are drinks included in the ticket price?

    A: No. Beverages, including beer, wine, and soft drinks, are available for purchase on board.


    Q: Is the boat accessible for guests with mobility issues?

    A: There are steps to board and narrow walkways, so mobility may be limited. Notify the crew in advance for assistance.


    Q: Are children allowed on board?

    A: Yes, but all passengers, regardless of age, must have a paid ticket.


    Q: What should I bring or wear?

    A: Wear comfortable, non-slip shoes and bring sunscreen, sunglasses, and a light jacket or sweater.


    Q: Where can I park for the Stars and Stripes sail?

    A: Parking is available inside Sea Pines Resort near Harbour Town. There is a gate fee per vehicle to enter the resort, and from the parking area it’s a short walk to the Harbour Town Pier.

    Cancellation policy

    Receive a full refund when you cancel at least 48 hours before departure or if the operator cancels due to weather or insufficient passengers. No-shows are charged the full price.

    Perfect for

    • Couples seeking a romantic Hilton Head afternoon with ocean views and champagne
    • Groups of friends wanting an active yet relaxed coastal adventure together
    • Families looking for a unique, memorable experience kids will actually enjoy
    Experience provided by Vagabond Cruise
    Experience provided by Vagabond Cruise

    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 (650) 414-7338

    Reference #527SE5

    Person

    $49.95

    Public sail limited to 20 people

    0

    Private Sail

    $1,000

    For up to 26 people

    0

    Why book through Greetwell?

    • Greetwell Approved

      This experience meets our quality and safety standards

    • Includes Concierge Support

      Our team is here to help with questions, timing, or special requests

    • Flexible Cancellation

      Plans change? Most experiences offer flexible cancellation

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    Discover what we've curated for you

    Meeting location

    149 Lighthouse Rd. Hilton Head Island, SC 29928

    4.8 stars• 7.5K reviews

    Review summary

    4.8
    Excellent
    7.5K reviews•Google Maps

    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.

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