Private Sailing Lessons

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, 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 are 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. Private lessons are also a great way to prepare for our ASA certification courses.

Choose Your Vessel

⛵ Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch that offers a traditional and authentic sailing experience. With her classic wooden design and traditional rigging, Lady Patty is ideal for students who want to learn the fundamentals of sailing and understand how wind, sails, and boat balance work together.

Students can take the helm, assist with sail handling, and learn basic sailing techniques under the guidance of our experienced captains. The intimate size of the boat makes it easy to observe how each adjustment affects the boat’s performance.

Private lessons aboard Lady Patty provide a hands-on introduction to traditional sailing on the Chesapeake Bay.

⛵ Epiphany – Modern Catamaran

For those interested in modern cruising boats, lessons are also available aboard Epiphany, our spacious Leopard 44 cruising catamaran.

Epiphany provides a stable platform for learning a wide range of sailing and boat-handling skills, including sail trimming, maneuvering under power, docking techniques, and understanding catamaran systems. Her wide beam and open layout allow students to move comfortably around the boat while learning.

Because Epiphany is a modern cruising catamaran commonly used for charter and offshore cruising, lessons aboard this vessel are especially valuable for sailors who hope to charter boats in destinations such as the Caribbean or Mediterranean.

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 for emergency use, and Epiphany features a private, spacious marine head. Both are located down a short set of steps. 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 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 areas such as 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.