We're here to help
    Book online or call (650) 414-7338
    1. Local experiences/
    2. Yorktown, VA/
    3. Water Activities/
    4. Sailing/
    5. Hoist Sails & Fire Cannons on Pirate Cruise
    Why travelers choose Greetwell
    Curated by our team

    Every experience is selected and approved for quality and safety

    Personal concierge

    Real humans available to help before, during, and after your booking

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else

    Easy booking

    Reserve in minutes with flexible cancellation on most experiences

    Greetwell

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners

    Concierge Support

    • Help Center
    • (650) 414-7338
    • Contact our team

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Hoist Sails & Fire Cannons on Pirate Cruise

    Join a kid-friendly schooner cruise to hoist sails, fire the cannon, and earn your pirate stripes

    From$48/ person

    Duration

    1.5 hrs

    Includes

    Schooner cruise, Pirate activities

    Highlights

    Set sail aboard a historic schooner for a lively pirate-themed cruise on the York River. Kids become the crew as they raise sails, steer the helm, and learn seafaring skills while adults relax and enjoy the view.

    • Hoist the sails alongside the crew for wind-powered fun
    • Steer the schooner under the captain's guidance
    • Learn essential sailor knots and maritime skills
    • Show off temporary pirate tattoos for great photos
    • Hear the boom of the ship's cannon across the water

    What's Included

    • 1.5-hour schooner sail on the York River
    • Interactive pirate activities for kids
    • Use of life jackets and safety gear

    Things to know

    Cruise operates May through September and select spring break dates. Wear flat-soled shoes and bring a jacket in cooler weather. No outside food, coolers, or large items allowed aboard.

    Cancellation policy

    No refunds except for captain-determined weather cancellations. If a sailing is cancelled due to weather you will be offered to reschedule, receive a gift certificate, or obtain a refund. No-shows and late arrivals receive no refund.

    Meeting location

    425 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 #YM8NAT

    Adult

    $48.15

    Ages 13+

    0

    Child

    $37.45

    Ages 12 & Under

    0

    Infant

    $0

    Under 12 Months Old • Must Book 1 Adult First

    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

    Search all experiences

    Discover what we've curated for you

    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

    Nearby activities

    Thumbnail

    Private Yoga Instructor to Your Vacation Rental

    $80/ person
    Thumbnail

    Yorktown Sunset Sail on Historic York River

    $58.85/ person
    Thumbnail

    Norfolk Electric Bike Rental: Full Day Cruiser

    From$74
    Thumbnail

    Norfolk E-Bike Rental: Elizabeth River Trail

    From$47