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    1. Local experiences/
    2. Yorktown, VA/
    3. Water Activities/
    4. Sailing/
    5. Yorktown Sunset Sail on Historic York River
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    Yorktown Sunset Sail on Historic York River

    Relax on a two-hour evening cruise along the York River and watch the sun set over historic Yorktown.

    From$58/ person

    Duration

    2 hrs

    Includes

    2-hour sail, Crew, Cash bar

    Highlights

    Sail into the evening aboard the tall ship Alliance II and experience tranquil views of the York River as the sun dips below the horizon. Enjoy the sounds of the wind in the sails while the crew points out historic landmarks and local wildlife.

    1. Glide past 18th Century waterfront homes and the Yorktown Battlefield
    2. Spot dolphins, osprey and other river wildlife
    3. Purchase beer, wine or snacks from the ship's galley
    4. Lend a hand setting the sails with guidance from the crew
    5. Capture sunset photos from open deck seating

    Things to know

    Not recommended for young children. Outside alcohol, coolers and large items are not permitted. Wear flat-soled shoes for safe footing.

    Cancellation policy

    No refunds except when the captain cancels for weather. Cruises run rain or shine. No-shows are charged in full, and late arrivals who miss the ship receive no refund.

    Meeting location

    Riverwalk Landing Pier, 331 Water St, Yorktown, VA 23690

    Experience provided by Yorktown Sailing Charters
    Experience provided by Yorktown Sailing Charters

    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 #XH2BTG

    Person

    $58.85

    All Ages

    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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    4.7 stars• 1.9K reviews

    Review summary

    4.7
    Excellent
    1.9K reviews•Google Maps

    Sailing with this crew is consistently described as a highlight of visiting the Yorktown area. The captains and staff earn overwhelming praise for being friendly, knowledgeable, and genuinely engaging. Passengers appreciate the historical narration that brings the York River and surrounding area to life, with crew members like Darby getting specific shoutouts for their storytelling abilities. The fleet includes schooners like the Alliance II and Serenity, offering everything from pirate-themed adventures for kids to romantic sunset cruises. The experience strikes a nice balance between relaxation and activity. Many guests mention getting hands-on opportunities to help raise sails, spotting dolphins, and enjoying the surprisingly comfortable conditions even on hot days thanks to shade from the sails. Light snacks are available at reasonable prices. Repeat visitors note that quality has remained excellent even through ownership changes, with families returning year after year for different cruise options. Whether you're looking for educational value, a special celebration, or simply a beautiful way to spend an afternoon on the water, the crew makes sure everyone has a memorable time.

    What people are saying

    Review 1 of 5
    5/5

    There is nothing like sharing a picnic on a pirate ship. We gad such a great experience aboard the Alliance Schooner. A special thank you to the captain and his staff for helping to make our trip very memorable and enjoyable. We have done all of the different trips with them over the years and I can definitely say we have never been disappointed. Why go anywhere else when we can vacation in our own backyard. Williamsburg, Yorktown and Jamestown has so much to offer. Thank you again for making this day special.

    Photo of June Yuiska

    June Yuiska

    September 4, 2025

    Review 1 of 1
    5/5

    There is nothing like sharing a picnic on a pirate ship. We gad such a great experience aboard the Alliance Schooner. A special thank you to the captain and his staff for helping to make our trip very memorable and enjoyable. We have done all of the different trips with them over the years and I can definitely say we have never been disappointed. Why go anywhere else when we can vacation in our own backyard. Williamsburg, Yorktown and Jamestown has so much to offer. Thank you again for making this day special.

    Photo of June Yuiska

    June Yuiska

    September 4, 2025

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