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    1. Local experiences
    2. /Things to do in Saint Michaels…
    3. /Water Activities
    4. /Sailing
    5. /Chesapeake Bay Day Sail on a 1935 Ketch in St. Michaels
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    Chesapeake Bay Day Sail on a 1935 Ketch in St. Michaels

    Sail a Historic 1935 Ketch on the Miles River

    5.0 stars• 1.4K reviews

    Duration

    2 hours

    Ideal For

    Up to 13 people

    Includes

    Bottled water, rain jackets

    Highlights

    Step aboard the historic Lady Patty for a relaxed sail through the harbor, Miles River, and Chesapeake Bay. Add a beer and wine tasting for $20 per person if you’re 21 or older.

    • Explore the harbor, Miles River, and Chesapeake Bay under sail
    • Look for osprey, bald eagles, and occasional dolphins
    • Join the working crew or relax on deck
    • Purchase soda, beer, wine, and champagne onboard

    What's Included

    • Bottled water
    • Binoculars
    • Rain jackets
    • Free parking

    Important details

    • All ages welcome
    • Children under 13 must wear a life preserver while aboard
    • A minimum of 2 people is required for the experience to take place
    • Amusement tax and crew gratuity are added to the listed price; amounts are not specified

    Cancellation Policy

    Per-person reservations: full refund up to 24 hours before departure. Private 2-hour charters: full refund more than 7 days before; 50% refund from 72 hours to 7 days before; no refund within 72 hours. Full refund if the operator cancels due to weather or unforeseen circumstances. No-shows are charged full price.

    Product ID: BGAEZT

    FAQs

    Arrive 15 minutes before departure.

    Wear comfortable shoes that are easy to remove. Barefoot is welcome, but high heels are not permitted.

    Restrooms are available inside the hotel. A head (toilet) is also available onboard, but you are encouraged to use the hotel facilities before boarding.

    Meeting details

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

    Experience provided by St. Michaels 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 1-877-GREET-WELL

    Report an issue

    Passenger

    $131.48

    All ages welcome!

    0

    Private Charter

    $1,377.08

    Up to 13 people | All ages welcome!

    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

    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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