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

    Sail Hilton Head’s coast aboard the historic Stars & Stripes

    4.8 stars• 8K reviews

    Duration

    1.5 Hours

    Ideal For

    Up to 29 people

    Includes

    Sailing, dolphin viewing

    Highlights

    Step aboard the America’s Cup 12 Meter Stars & Stripes for an afternoon on Hilton Head’s coastal waters. Relax on deck or help the crew sail while watching for Atlantic bottlenose dolphins.

    • Explore Hilton Head’s coastal waters aboard a historic America’s Cup yacht
    • Join the crew and help sail, or relax on deck
    • Watch for Atlantic bottlenose dolphins along the coast
    • Enjoy deck-cushion seating close to the water
    • Purchase beer, wine, soda, and water on board

    What's Included

    • Opportunity to participate as a crew member
    • Small onboard restroom

    Important details

    • Arrive 45 minutes before departure; boarding begins 30 minutes before departure
    • All ages require a ticket
    • Boarding requires steps, and walkways around the boat are narrow
    • The boat is not wheelchair accessible
    • A $10 per-vehicle Sea Pines Resort entry fee applies when arriving from outside the resort

    Cancellation Policy

    Receive a full refund with at least 48 hours' notice of cancellation. Full refund if the operator cancels due to weather or other unforeseen circumstances. No-shows are charged the full price.

    Product ID: G627NN

    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.

    Experience provided by Vagabond Cruise

    Related locations

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    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

    Private Sail

    $1,444.50

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

    0

    Why book through Greetwell?

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      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
    8K 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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