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    1. Local experiences
    2. /Things to do in Hilton Head Island…
    3. /Water Activities
    4. /Sailing
    5. /Hilton Head Sunset Sail on Stars & Stripes
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    Hilton Head Sunset Sail on Stars & Stripes

    Watch Hilton Head's vibrant sunset while relaxing or helping crew aboard the historic Stars & Stripes

    4.8 stars• 8.1K reviews

    Duration

    2 Hours

    Ideal For

    26 people

    Includes

    Sunset sail, Crew commentary

    Highlights

    Set sail aboard the iconic America's Cup 12-Meter Stars & Stripes and watch the Lowcountry sky glow as the sun sinks behind Daufuskie Island. Relax on deck cushions or lend a hand to the crew for an unforgettable evening on Hilton Head Island.

    1. Marvel at sweeping views of marshes and coastline
    2. Choose to hoist sails with the crew or simply unwind
    3. Capture vibrant sunset photos from the open deck
    4. Purchase beer, wine, and soft drinks on board
    5. Spot playful dolphins and hear local history

    What's Included

    1. Two-hour sunset sail aboard Stars & Stripes
    2. Option to assist the crew sailing the vessel
    3. Onboard commentary and scenic photo opportunities

    Things to know

    The vessel is not wheelchair accessible and requires navigating steps and narrow walkways. Recommended for ages 3 and up; seating is on deck cushions.

    Cancellation Policy

    Receive a full refund when you cancel at least 48 hours before departure or if the operator cancels due to weather or unforeseen circumstances. Cruises require a minimum number of passengers; if this is not met you may rebook or receive a full refund. No-shows are charged the full price.

    Product ID: QQKHHT

    FAQs

    Yes, guests ages 3 and up are welcome. All passengers, regardless of age, need their own ticket.

    Outside beverages are not permitted, but beer, wine, and non-alcoholic drinks are available for purchase on board.

    Wear comfortable, non-slip shoes and bring a light jacket or sweater for cooler weather. Sunscreen, a hat, and sunglasses are recommended.

    Meeting details

    Harbour Town Pier, 149 Lighthouse Rd., Hilton Head Island, SC 29928

    Experience provided by Vagabond Cruise

    Perfect for

    • Couples seeking a romantic Lowcountry evening with sunset views and quality time on the water
    • Families with kids 3+ looking for an interactive sailing adventure that's both educational and fun
    • Friend groups wanting a unique girls' trip or guys' getaway with hands-on sailing and cocktails

    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

    Person

    $76.72

    Limited 20 public guests | U.S. Coast Guard approved for 36.

    0

    Private Sail

    $1,805.63

    For 26 passengers or less | Includes taxes and service charge.

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.8
    Excellent
    8.1K 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

    Good trip on a nice boat. Very good crew and we saw lots of Dolphins!

    Photo of Kevin Spence

    Kevin Spence

    September 1, 2026

    Review 1 of 1
    5/5

    Good trip on a nice boat. Very good crew and we saw lots of Dolphins!

    Photo of Kevin Spence

    Kevin Spence

    September 1, 2026

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