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    1. Local experiences
    2. /Things to do in Hilton Head Island…
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    5. /Hilton Head Island Sunset Sailing Charter
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    Hilton Head Island Sunset Sailing Charter

    Sail a historic 12 Meter yacht at sunset from Harbour Town

    4.8 stars• 7.9K reviews
    From$1,647incl. taxes and fees

    Duration

    2 Hours

    Ideal For

    Up to 29 people

    Includes

    Private sail, taxes, service charge

    Highlights

    Sail aboard Stars & Stripes, a 12 Meter America’s Cup yacht once skippered by Dennis Connor. Enjoy a private sunset charter from Harbour Town with views of Daufuskie Island and the saltwater marshes.
    • Step aboard a historic America’s Cup yacht
    • Choose to help sail or relax on deck cushions
    • Take in views of Daufuskie Island and saltwater marshes
    • Bring a private group of up to 29 passengers
    • Purchase beer, wine, prosecco, soda, and water on board

    Know before you go

    • Arrive 45 minutes before your scheduled departure; boarding begins 30 minutes before departure
    • Pay a $10 per-vehicle Sea Pines Resort entry fee if staying outside the resort
    • All guests, including infants, count toward the 29-passenger maximum
    • Access requires steps, and walkways around the boat are narrow
    • The boat is not wheelchair accessible

    Cancellation Policy

    Full refund with 48 hours' notice. No-shows are charged in full. 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.

    Yes. The boat has a small restroom, called a head, reached by a set of steps.

    Guests typically stay dry, but wind conditions and sea spray may leave you a little damp. Bring a light jacket or waterproof layer for your private sail.

    Experience provided by Vagabond Cruise
    Experience provided by Vagabond Cruise

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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

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    Reference #6G4KHQ

    Private Sail

    $1,647.80

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

    0

    Why book through Greetwell?

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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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