BaySail School of Sailing LLC is a Chesapeake Bay–based sailing school operating out of Havre de Grace that offers hands‑on, skill‑focused instruction for beginners and aspiring skippers. The school delivers American Sailing Association (ASA) courses including ASA 101, ASA 103, ASA 104 and ASA 118, plus introductory one‑day classes and yacht rentals. Instruction occurs on stable small boats and keelboats — Capri 22 daysailer classes, 20–27 foot keelboats for basic training, and live‑aboard charters for coastal cruising certification on 30–45 foot sloops. Several courses limit enrollment to small groups (often four students) to ensure personalized coaching and practical seat‑time at the helm.
The five‑day Basic Coastal Cruising and Bareboat Cruising course combines live‑aboard experience on the Chesapeake Bay with navigation, safety, and seamanship training aimed at certifying skippers to handle larger yachts. Shorter offerings include a two‑day semi‑private ASA 101, a three‑day weekend ASA 101, and a one‑day Introduction to Sailing ideal for families and first‑time sailors. A focused one‑day ASA 118 Docking Endorsement teaches close‑quarters maneuvering and docking skills in small group sessions. BaySail also lists a Beneteau 41 half‑day rental option for private time aboard a larger yacht. Scheduling includes weekend, weekday and semi‑private formats. Some courses provide equipment and safety briefings as part of hands‑on training for students.