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    1. Local experiences
    2. /Things to do in St. Michaels…
    3. /Water Activities
    4. /Sailing
    5. /Private Sailing Charter in St. Michaels
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    Private Sailing Charter in St. Michaels

    Sail the Miles River aboard a historic 1935 ketch

    5.0 stars• 1.4K reviews

    Duration

    4.5 hours

    Ideal For

    Up to 13 people

    Includes

    Private boat, bottled water, gear

    Highlights

    Step aboard Lady Patty, a 1935 ketch, for an exclusive sail from St. Michaels. Start with waterfront views on a brief harbor cruise, then let the wind guide you on the Miles River.

    • Cruise past St. Michaels waterfront views on a mini harbor tour
    • Raise the sails and follow the wind on the Miles River
    • Customize your outing with pre-ordered food options from local businesses
    • Add a sunset Champagne cruise to afternoon sail times
    • Sample a beer and wine tasting add-on for ages 21 and older

    What's Included

    • Bottled water
    • Binoculars
    • Rain jackets
    • Hats
    • Blankets
    • Parking

    Important details

    • Children under 13 must wear a life preserver while aboard
    • Amusement tax and crew gratuity apply and are not included in the listed price

    Cancellation Policy

    Full refund if the operator cancels due to weather or other unforeseen circumstances. No-shows are charged the full price.

    Product ID: E9UDGV

    FAQs

    Bring your own food aboard. Outside alcoholic beverages are not permitted. Bottled water is included, and beer, wine, champagne, soda, and sparkling water are available for purchase onboard.

    Wear comfortable shoes that are easy to remove, or go barefoot. Do not wear high heels. Apply spray sunscreen before boarding.

    The captain may cancel for weather, with the final decision made about 15 minutes before departure. If the charter is cancelled, you can receive a rebooking, gift card, or refund.

    Meeting details

    Dock behind Harbor Inn & Marina, 101 N Harbor Rd, St. Michaels, MD 21663

    Experience provided by St. Michaels Sailing Charters

    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 Charter

    $2,622.68

    Up to 13 people | All ages welcome!

    0

    Why book through Greetwell?

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      No booking or service fees, ever

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

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      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    What people are saying

    Review 1 of 5
    5/5

    We had a great time out on the water with Rob (captain) and Steph. They not only sailed us around the Miles River, but also shared a general history of St. Michaels and the area. It was an enjoyable trip, and we would happily do it again!

    Photo of Jason Lombard

    Jason Lombard

    September 1, 2026

    Review 1 of 1
    5/5

    We had a great time out on the water with Rob (captain) and Steph. They not only sailed us around the Miles River, but also shared a general history of St. Michaels and the area. It was an enjoyable trip, and we would happily do it again!

    Photo of Jason Lombard

    Jason Lombard

    September 1, 2026

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