Boats at anchor on the Chesapeake Bay
Sail the Chesapeake Bay

Classes We Offer & Descriptions

The Gratitude Sailing Institute is where your transformative sailing journey begins.™

Click on the class names below to read the objectives for each course.

Learn to captain a 20'-27' sloop-rigged keelboat by day, in light to moderate winds and sea conditions. Learn basic sailing terminology, boat parts and functions, helm commands, basic sail trim, points of sail, buoyage, seamanship, and safety, including basic navigation rules to avoid collisions and hazards.

Learn to captain a 20'-30' sloop-rigged keelboat by day in winds up to 20 knots. Course emphasis is on mastering sail trim, and the effect of sail shape on power and speed. Depart, sail, and return with control, demonstrating teamwork.
(Prerequisite: ASA 101)

Learn to command a sloop-rigged auxiliary powered 25'-35' keelboat by day in moderate winds and sea conditions. Learn cruising sailboat terminology, basic boat systems, auxiliary engine operation, docking procedures, intermediate sail trim, navigation rules, basic coastal navigation, anchoring, weather, safety, and seamanship.
(Prerequisite: ASA 101)

Learn how to command a sloop-rigged, auxiliary powered 30'-45' sailboat during a multi-day cruise upon inland/coastal waters in moderate to heavy winds and sea conditions. Learn about provisioning, boat systems, auxiliary engines, advanced sail trim, coastal navigation, anchoring and mooring, docking, emergency operations, weather, and more.
(Prerequisites: ASA 101 & ASA 103)

ASA 105 Coastal Navigation teaches the foundational skills necessary for safe and effective passage planning and navigation in coastal waters. You’ll learn to read and interpret nautical charts, use tide and current tables, and understand key navigation publications like the USCG Navigation Rules. The course covers plotting positions, correcting for current and leeway, and converting between true and magnetic bearings. Practical exercises include plotting dead reckoning positions, determining a course to steer, and taking bearings to find your location. By the end of the course, you’ll have the tools and knowledge to confidently plan and execute coastal passages with accuracy and safety.

At The Gratitude Sailing Institute, on-water coastal navigation skills elements are contained in ASA 101, ASA 103, ASA 104, & ASA 106 in progressively increasing levels of detail.

It’s important to understand that simply enrolling in an ASA 105 course and attending classes doesn’t automatically guarantee certification. Our commitment is to the safety and competence of every sailor who takes to the water. From sail trim to navigation, we hold you to a high standard, so when you earn your certification, you know you’re truly ready to sail with skill and confidence. Safety isn’t just a lesson - it's our priority, and these standards are what set you up for success on the water.

Learn to operate a dinghy with an outboard motor safely and efficiently, in a variety of environments, including operating from a dock, a beach, and a cruising yacht. Understand the types of dinghies and outboards, characteristics of each, safe operation, security, towing, hoisting, storage, transit, deployment, care, and maintenance.

Learn basic docking skills for boats with single inboard or outboard engines. Discover the basic theory and hands-on techniques needed to dock and undock boats in an efficient manner and without damage or injury.

The wind and the water are waiting for you.

Reserve your spot before the 2026 season is full.

From a student who sailed with us

I completed 101 and 103 with Captain Frank in 2022 so I had high expectations for the 102 and 104 classes in May 2025. Captain Frank and Gratitude did not disappoint. The book and curriculum materials were available well in advance with clear guidance on how to utilize these for success during the course. The instruction was well organized, had a logical flow and Captain Frank never wasted a teaching moment nor was any question ever too small. Captain Frank's knowledge and experience are vast and he truly enjoys mentoring newer sailors which made the whole class exceptional.
We were fortunate to have mostly very fresh breezes which allowed for lots of practice with critical thinking and adapting to conditions for our sail plan each day. I found being able to learn from a master sailor like Captain Frank during gusty conditions was priceless and VERY helpful for my skill and overall confidence. I highly recommend Gratitude Sailing Institute for the individualized instruction from experts, always honest performance feedback and well honed logistics.

Catherine G.
ASA 101, 103 & 104 graduate

Taught by the people who know and sail the Bay

U.S. Coast Guard Licensed Captains and Master Captains, with hundreds of years of combined teaching experience — patient instructors, serious about safety.

Captain Frank McKee Captain Gary Hutson Captain Julie Tipton Captain Bob Baginski Captain Andrew Seligman Captain Dan Purcell
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