Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    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
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 3
    Product image 4
    Product image 5
    Product image 6
    Product image 7
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Chesapeake Bay Wine Tasting Cruise From St. Michaels

    Sip six curated wines while sailing St. Michaels’ waterfront

    5.0 stars• 1.3K reviews
    From$186/ personincl. taxes and fees

    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

    Know before you go

    • 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.

    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
    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

    Reference #EGH9NU

    Passenger

    $186.84

    All ages welcome!

    0

    Private Charter

    $2,069.08

    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 4
    5/5

    We had the most fabulous sunset cruise with the Selina II! Iris and her first mate, Matt, where the best. We were worried that our sail might be cancelled because of the hurricane winds and the rain, but the day ended up clearing and the sun came out for a breathtaking sunset. Even though we have lived in St. Michael's for 13 years, we learned so much that we never new about the area. It was truly a delight and would highly recommend to both locals and tourist!

    Photo of Beth Berquist

    Beth Berquist

    October 16, 2025

    Review 1 of 1
    5/5

    We had the most fabulous sunset cruise with the Selina II! Iris and her first mate, Matt, where the best. We were worried that our sail might be cancelled because of the hurricane winds and the rain, but the day ended up clearing and the sun came out for a breathtaking sunset. Even though we have lived in St. Michael's for 13 years, we learned so much that we never new about the area. It was truly a delight and would highly recommend to both locals and tourist!

    Photo of Beth Berquist

    Beth Berquist

    October 16, 2025

    Nearby activities

    Thumbnail
    SailingUp to 13

    2-Hour Chesapeake Bay Day Sail in St. Michaels

    From$159/ person
    Thumbnail
    Wine TastingMax 6

    Wine Tasting Cruise in St. Michaels

    From$297/ person
    Thumbnail
    SailingUp to 13

    Private Sailing Catamaran Charter in St. Michaels

    From$1,576
    Thumbnail
    Engagement PackagesUp to 6

    St. Michaels Marriage Proposal Cruise

    $1,515.48
    Thumbnail
    Yacht ChartersUp to 6

    Bachelorette & Bachelor Party Cruise in St. Michaels

    $1,377.08
    Thumbnail
    SailingUp to 6

    Sunset Champagne Cruise in St. Michaels

    From$297/ person