Do I need prior sailing experience?

No — lessons accommodate beginners through intermediate sailors; instructors start with basics and scale drills to the group.

Where do we meet for the lesson?

Meet at Harbour Inn, 101 N. Harbor Rd, St. Michaels, MD 21663; arrive 15 minutes early to check in at the dock.

What is the maximum group size?

Private lessons are for up to 13 guests, allowing hands‑on time for each participant.

Is the 1935 ketch suitable for rough conditions?

Lady Patty is a sturdy Maryland-built ketch; instructors will adjust scope and exercises according to weather and sea state for safety.

There is no published minimum age in the listing; contact the operator if you plan to bring young children to confirm suitability and safety measures.

What about seasickness?

If you’re prone to seasickness, take preventive measures (medication, acupressure bands, light meal) and let the instructor know — calmer waters are chosen when possible.

Private Sailing Lesson Aboard the 1935 Ketch Lady Patty in St. Michaels | Private | Sailing

Adventure Brief

Two hours aboard a 1935 Maryland-built ketch teach you sail handling, knots, tacking, and wind reading in a small private group. Departing from Harbour Inn in St. Michaels, this hands-on lesson is ideal for curious novices and sailors polishing fundamentals.

2 hours

moderate

From $1,515.15

On the water off Maryland’s Eastern Shore, Private Sailing Lesson on Lady Patty offers a compact, hands-on introduction to traditional sailing aboard a historic 1935 ketch. Departing from Harbour Inn, 101 N. Harbor Rd, St. Michaels, MD 21663, the two‑hour session is designed for individuals or small groups (maximum 13) who want to move beyond theory and feel wind and rig under their own hands. The Lady Patty is Maryland-built and carries classic lines and period fittings; the boat’s gaff rig, wooden accents, and sturdy hull make every maneuver tactile and memorable. Instruction blends sail handling, line work, knotcraft, tacking drills, and basic navigation and weather awareness so students leave confident to skipper small daysails. Coaching alternates demonstration, guided practice, and repeated reps of maneuvers—raising sails, trimming sheets, coming about, and steering close‑hauled or on a broad reach. Instructors explain the four points of sail, how to read the wind and current on Chesapeake flats, and the basic navigation rules that keep you safe among dayboats and working watermen. Because the lesson runs from a dock at the Harbour Inn & Marina, check‑in is fifteen minutes before departure to stow bags and get a safety brief. Skill levels range from total novice to sailors polishing fundamentals; no prior certification is required but steady balance and curiosity help. The lesson’s small group format and historic platform make it a stand‑out offering in St. Michaels, where commercial charters dominate; here you trade passive sightseeing for active learning on a boat with character and history. Expect to glimpse osprey quartering the shoreline, working oyster beds, and the craggy shoreline of the Miles River as you practice maneuvers in real conditions. Whether you aim to helm confidently, tie essential knots, or just understand wind and trim better, this private lesson offers concentrated time on deck and skills you can use immediately on Bay waters. Book through the provided referral link to confirm availability and plan to arrive prepared with layered clothing, non‑marking shoes, sunscreen, and a ready sense of curiosity. Lady Patty’s presence preserves a living link to Chesapeake maritime craft; learning aboard her supports local maritime heritage and complements nearby options like day charters and paddle trips by offering education rather than transport. Small groups mean more helm time and immediate correction from instructors, accelerating learning compared with crowded lessons. The two‑hour format is compact enough to fit a travel day but substantive enough to leave you performing confident tacks and handling lines. St. Michaels’ easy access from Annapolis makes this a practical stop for sailors and travelers. For visitors who want to translate waterfront curiosity into competence, this lesson is an efficient, authentic, memorable way to go afloat, and you'll want more.