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    1. Local experiences
    2. /Things to do in St. Michaels…
    3. /Wine and Spirits
    4. /Wine Tasting
    5. /Chesapeake Bay Wine Tasting Cruise From St. Michaels
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    Chesapeake Bay Wine Tasting Cruise From St. Michaels

    Sip six curated wines while sailing St. Michaels’ waterfront

    5.0 stars• 1.4K reviews

    Duration

    2 hours

    Ideal For

    Up to 13 people

    Includes

    Six wines, harbor tour, sailing

    Highlights

    Set sail aboard the historic 1935 ketch Lady Patty for a wine tasting cruise on Chesapeake Bay. Take in St. Michaels waterfront views and a mini-harbor tour as you sample curated wines.

    • Explore the harbor on a mini-harbor tour
    • Savor three red and three white wines
    • Relax aboard the historic 1935 ketch Lady Patty
    • Discover a regularly changing selection of global wines
    • Enjoy attentive service from the crew

    What's Included

    • Six wine tastings
    • Mini-harbor tour

    Important details

    • Wine tasting requires age 21+
    • A minimum of 2 people is required for the experience to operate
    • 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

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

    Product ID: EGH9NU

    FAQs

    Wear comfortable shoes that are easy to remove. Bare feet are welcome; high heels are not permitted.

    Bring your own food. Outside alcoholic beverages are not permitted aboard Lady Patty. Complimentary bottled water is included, and additional beverages are available for purchase onboard.

    Use the hotel restrooms before boarding when possible. A restroom is also available onboard.

    Meeting details

    Dock behind 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

    $159.16

    All ages welcome!

    0

    Private Charter

    $1,653.88

    Up to 13 people | All ages welcome! | Must be age 21+ to participate in tastings

    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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