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    1. Local experiences/
    2. Things to do in St. Michaels…/
    3. Water Activities/
    4. Sailing/
    5. 2-Hour Chesapeake Bay Day Sail in St. Michaels
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    2-Hour Chesapeake Bay Day Sail in St. Michaels

    Sail the Chesapeake on a 1935 ketch with the option to join the crew

    5.0 stars• 1.3K reviews
    From$131/ personincl. taxes and fees

    Duration

    2 hours

    Ideal For

    Up to 13 people

    Includes

    Bottled water, binoculars

    Highlights

    Enjoy a relaxed two-hour sail aboard the historic Lady Patty, departing from St. Michaels. Cruise through the harbor and out on the Miles River for shoreline views and possible wildlife sightings.

    • Board a 1935 Maryland-built ketch for a two-hour day sail
    • Glide through the harbor before cruising the Miles River and Chesapeake Bay
    • Choose a public sail or book a private charter for your group
    • Join in as working crew or relax on deck
    • Look for osprey, bald eagles, and occasional dolphins

    What's Included

    • Bottled water
    • Binoculars
    • Rain jackets
    • Free parking

    Things to know

    Maximum 13 people. Amusement tax and crew gratuity are added on—confirm the amount with Greetwell before booking. Beer and wine tasting is available as an add-on for an additional $20 per person (21 and older).

    Cancellation Policy

    Per-person: full refund if you cancel 24+ hrs before departure. Private charter: full refund if you cancel 7+ days before; 50% refund if less than 7 days and more than 72 hrs; no refunds within 72 hrs. No-shows charged full price. Full refund if operator cancels due to weather.

    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

    Harbour Inn, 101 N. Harbor Rd, St. Michaels, MD 21663

    Experience provided by St. Michaels Sailing Charters
    Experience provided by St. Michaels Sailing Charters

    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 (650) 414-7338

    Report an issue

    Reference #BGAEZT

    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

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