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    1. Local experiences
    2. /Things to do in Saint Michaels…
    3. /Wine and Spirits
    4. /Wine Tasting
    5. /2-Hour Wine Tasting Cruise in St. Michaels
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    2-Hour Wine Tasting Cruise in St. Michaels

    Sample Six Curated Wines While Sailing Chesapeake Bay

    5.0 stars• 1.4K reviews

    Duration

    2 hours

    Ideal For

    Up to 6 people

    Includes

    Six wines, mini-harbor tour, sail

    Highlights

    Set sail from St. Michaels for a relaxed wine tasting experience on Chesapeake Bay. Sample curated wines as you take in waterfront views from a modern catamaran.

    • Explore Chesapeake Bay aboard a 2016 44-foot catamaran
    • Take in views of the St. Michaels waterfront from the water
    • Enjoy changing selections of wines from around the world
    • Relax with service from the onboard crew

    What's Included

    • Six curated wines: three reds and three whites
    • Mini-harbor tour
    • Sailing cruise

    Important details

    • Ages 21+ only
    • Amusement tax and crew gratuity are added to 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, 50% refund 72 hours to 7 days before, and 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: PY9QVZ

    FAQs

    Arrive 15 minutes before departure at the dock behind the Harbor Inn & Marina.

    Wear comfortable shoes that are easy to remove. Barefoot is welcome. Do not wear high heels.

    Use the restrooms inside the hotel before boarding. There is also a head (toilet) onboard.

    Meeting details

    Dock behind Harbour 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

    $297.56

    All ages welcome!

    0

    Private Charter

    $1,515.48

    Up to 6 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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