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    1. Local experiences
    2. /Things to do in St. Michaels…
    3. /Water Activities
    4. /Sailing
    5. /Private Sailing Charter in St. Michaels
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    Private Sailing Charter in St. Michaels

    Sail the Miles River aboard a historic 1935 ketch

    5.0 stars• 1.3K reviews
    From$2,622incl. taxes and fees

    Duration

    4.5 hours

    Ideal For

    Up to 13 people

    Includes

    Private boat, bottled water, gear

    Highlights

    Step aboard Lady Patty, a 1935 ketch, for an exclusive sail from St. Michaels. Start with waterfront views on a brief harbor cruise, then let the wind guide you on the Miles River.
    • Cruise past St. Michaels waterfront views on a mini harbor tour
    • Raise the sails and follow the wind on the Miles River
    • Customize your outing with pre-ordered food options from local businesses
    • Add a sunset Champagne cruise to afternoon sail times
    • Sample a beer and wine tasting add-on for ages 21 and older

    What's Included

    • Bottled water
    • Binoculars
    • Rain jackets
    • Hats
    • Blankets
    • Parking

    Know before you go

    • 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

    Full refund if the operator cancels due to weather or other unforeseen circumstances. No-shows are charged the full price.

    FAQs

    Bring your own food aboard. Outside alcoholic beverages are not permitted. Bottled water is included, and beer, wine, champagne, soda, and sparkling water are available for purchase onboard.

    Wear comfortable shoes that are easy to remove, or go barefoot. Do not wear high heels. Apply spray sunscreen before boarding.

    The captain may cancel for weather, with the final decision made about 15 minutes before departure. If the charter is cancelled, you can receive a rebooking, gift card, or refund.

    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

    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 1-877-GREET-WELL

    Report an issue

    Reference #E9UDGV

    Private Charter

    $2,622.68

    Up to 13 people | All ages welcome!

    0

    Why book through Greetwell?

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      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

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