Spend a day on the Chesapeake Bay learning to sail with BaySail School of Sailing in Havre de Grace. This beginner-friendly full-day class offers hands-on instruction, making it perfect for families or friends ready to take the helm.
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Difficulty
easy
Duration
6–7 hours
Fitness Level
Moderate fitness recommended; must be able to stand and move about the boat safely throughout the day.
Wildlife
History
Havre de Grace has a rich maritime history as a key port on the Chesapeake since the 18th century.
Conservation
BaySail promotes sustainable boating practices to protect the bay’s delicate estuarine ecosystem.
BaySail School of Sailing LLC
Spend a day on the Chesapeake Bay learning to sail with BaySail School of Sailing in Havre de Grace. This beginner-friendly full-day class offers hands-on instruction, making it perfect for families or friends ready to take the helm.
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.
ASA Courses
ASA 101, 103, 104, 118
Basic to bareboat endorsements offered
Small Groups
Often 4 students
Personalized hands‑on instruction
Locations
Havre de Grace, Chesapeake Bay
Local waterways for coastal training
Vessels
Capri 22; 20–27ft keelboats; Beneteau 41
Range of training and rental boats
Reserve a spot in a BaySail course or book a yacht rental in Havre de Grace — small classes and practical training designed for measurable progress.
Arrive Early for Briefing
Plan to arrive at least 30 minutes early to complete orientation and get fitted with safety gear.
Dress for Water and Wind
Wear layers and bring waterproof clothing to stay comfortable on the bay’s changing conditions.
Sun Protection is Key
Bring sunscreen, sunglasses, and a hat — exposure doubles on the water under direct sun.
Minimum Class Size Required
Note that the class only runs with at least two students enrolled; check ahead to avoid cancellations.
Waterproof Jacket
Protects against wind and spray during cooler days on the bay.
spring
Sunglasses with UV Protection
Reduces glare from the water and protects eyes on sunny days.
summer
Non-slip Boat Shoes
Provides grip on wet decks and supports safe movement on board.
Wide-brimmed Hat
Offers additional sun protection during peak daylight hours.
summer