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

    Build Practical Sailing Skills With Private, Hands-On Instruction

    5.0 stars• 1.3K reviews
    From$1,377incl. taxes and fees

    Duration

    2 hours

    Ideal For

    Up to 6 people

    Includes

    Private lesson, water, gear

    Highlights

    Take the helm in a private lesson that introduces the fundamentals of sailing through hands-on practice. Build confidence with guidance suited to beginners and experienced sailors alike.
    • Practice line handling, sail raising, steering and reading the wind
    • Learn basic knots, points of sail, sail trim and tacking
    • Understand boat parts, simple handling and rules of the road
    • Explore the physics behind sailing toward the wind

    What's Included

    • Bottled water
    • Binoculars
    • Rain jackets
    • Hats
    • Blankets
    • Free parking

    Know before you go

    • Wear a life preserver if you are under age 13
    • Expect a 10% St. Michaels Harbor amusement tax, not included in the listed price
    • Expect a customary crew gratuity of 15%-20%, not included in the listed price

    Cancellation Policy

    Full refund if cancelled more than 7 days before start. 50% refund if cancelled less than 7 days and more than 72 hours before start. No refund if cancelled less than 72 hours before start. Full refund if the operator cancels due to weather or other unforeseen circumstances.

    FAQs

    Wear comfortable shoes that are easy to remove, or go barefoot. No high heels. Apply spray sunscreen before boarding.

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

    All ages are welcome. Children under 13 are required to wear a life preserver while aboard; infant, toddler, and youth life jackets are available.

    Meeting details

    Dock behind the 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 #FUARSX

    Private Sailing Lesson

    $1,377.08

    Up to 6 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

    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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