Private Sailing Lessons on Lady Patty

Your Sailing Lesson Experience

Your private sailing lesson begins in the charming harbor of historic St. Michaels, Maryland. After departing the marina, you’ll pass the 1879 Hooper Strait Lighthouse before heading out onto the scenic waters of the Miles River, a tributary of the Chesapeake Bay.

During your lesson aboard Lady Patty, our experienced captains guide you through hands-on sailing skills such as sail trim, steering, docking techniques, and understanding the wind and points of sail. The protected waters of the Miles River provide an ideal environment for learning.

Whether you’re brand new to sailing or looking to build confidence and refine your skills, private lessons allow you to learn at your own pace with personalized instruction in a relaxed and supportive setting. These lessons are also an excellent way to prepare for our ASA sailing certification courses.

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Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch that captures the elegance and craftsmanship of classic Chesapeake Bay sailing. With her traditional wooden construction and classic rigging, Lady Patty offers a hands-on sailing experience that connects students directly to the fundamentals of wind, sail balance, and boat handling.

Her traditional sail plan and responsive helm make Lady Patty an excellent platform for learning core sailing skills. During your lesson you’ll have the opportunity to take the helm, assist with sail handling, and observe how adjustments to sails and trim affect the boat’s movement through the water.

Lessons aboard Lady Patty provide an authentic sailing experience and a deeper understanding of traditional sailing techniques on the Chesapeake Bay.

Location

Our sailing lessons depart from the Harbour Inn & Marina in St. Michaels, Maryland, a charming Chesapeake Bay town known for its waterfront views, seafood restaurants, and maritime history.

Located on Maryland’s Eastern Shore, St. Michaels provides ideal sailing conditions with protected waters on the Miles River.

Good to Know Before You Go

Arrival:
Please arrive 15 minutes prior to departure at the dock behind the Harbour Inn & Marina, 101 N Harbor Road, St. Michaels, MD.

Restrooms:
Lady Patty has a small marine head available for emergency use. For all guests, we recommend using the Harbour Inn lobby restrooms before boarding.

Parking:
Guests may park in the hotel lot or along the waterfront on Harbor Road past the police boats.

Shoes & Attire:
Wear comfortable shoes or something easy to remove if you prefer to go barefoot. Light jackets or layers are recommended on cooler days.

Sunscreen & Hats:
If using spray sunscreen, please apply before boarding to protect the varnish. Don’t worry if you forget your sunhat — custom baseball caps are available for purchase onboard.

Children:
Children of all ages are welcome! Life jackets are available in infant, toddler, and youth sizes. Per U.S. Coast Guard regulations, all children count as passengers and require a ticket.

Weather:
Safety and comfort are our priority. The captain may cancel due to weather, with the final decision made about 15 minutes before departure. There is no charge if a sail is cancelled due to weather, and we will do our best to reschedule your lesson or provide a refund.

Beverages & Food:
A variety of beverage options are available for purchase. Bottled water is complimentary. We also partner with local businesses to offer pre-ordered, charter-friendly food options ready upon arrival. For full details on onboard food and beverage options, please see our policies.

Interested in ASA Sailing Certification?

Private sailing lessons are a great way to get comfortable on the water or refresh your sailing skills. For those looking to take the next step, St. Michaels Sailing Charters also offers American Sailing Association (ASA) certification courses.

Our ASA courses provide structured training and internationally recognized sailing certifications that allow sailors to confidently skipper cruising boats and charter vessels around the world.

Courses are taught aboard Epiphany, our Leopard 44 cruising catamaran, and include hands-on instruction in sail handling, docking, navigation, and coastal cruising skills.

👉 Learn more about our ASA sailing certifications here: ASA Sailing School Certifications

Ready to Set Sail?

Private sailing lessons are a great way to build confidence on the water, learn new skills, or prepare for ASA certification courses.

Reserve your lesson today and experience the joy of sailing on the Chesapeake Bay.