Gratitude Sailing logo

Where your transformative sailing journey begins™

×
Two sailors sharing a high five while sailing on the Chesapeake Bay
Northern Chesapeake Bay · Baltimore · Annapolis · Philadelphia · Washington, DC

The best sailing education happens twenty degrees off vertical.

Gratitude Sailing Institute turns an ordinary summer afternoon into real-world training that can't be learned on a video screen.

Three children sailing a boat together with a captain providing instruction
Why on-water training matters

Plug into the wind.

You don't need another activity that ends in staring at a screen. You need to feel the wind.

01

No wifi required

Out here, there's a jib to trim, a course to hold, and a horizon nobody can scroll past.

02

Everyone has a job

From the person at the helm to the one scouting crab pots in the water, every one on board matters to getting the boat home.

03

Confidence that's earned

There's no trophy for showing up. When the day is complete and the boat and its crew are safely back in its slip, the pride and knowledge is the award.

The course you'll chart

Every class is a chapter in your sailing story

Built on the internationally recognized American Sailing curriculum, each class is a full-length, hands-on session under a US Coast Guard licensed Captain — no shortcuts, no diploma-mill videos. Here's what each leg of the journey actually feels like.

ASA 101 · KEELBOAT SAILING 1

First Tack Together

This is the class where nobody's the expert yet — everyone starts from the same square one, hands on the same lines, laughing at the same first wobbly tack. It's the moment "I can't" quietly becomes "we did."

On the water: Basic sailing terminology, boat handling, helm commands, sail trim, points of sail, and collision-avoidance rules aboard a 20'–27' keelboat in light-to-moderate conditions.

ASA 102 · KEELBOAT SAILING 2

Trust the Wind, Trust Each Other

With the basics behind you, the whole crew starts working as one unit — perfecting sail trim, reading the wind, bringing the boat home under real control. It's teamwork with the training wheels off.

On the water: Mastering sail trim and sail shape in winds up to 20 knots aboard a 20'–30' keelboat; departing, sailing, and returning as a coordinated team. Prerequisite: ASA 101.

Water spraying onto the deck of a heeling sailboat on a sunny day
ASA 103 · COASTAL CRUISING

A Whole Day Away

Pack a lunch. This is the full-day escape — dropping anchor in a quiet cove, heaving-to, figuring out that "away from it all" is a feeling, not just a place on a map.

On the water: Commanding an auxiliary-powered 25'–35' keelboat: docking, intermediate sail trim, coastal navigation basics, anchoring, weather reading, and seamanship. Prerequisite: ASA 101.

ASA 104 · BAREBOAT CRUISING

Sleep Aboard, Wake Up Free

Multiple days, one boat — mornings with coffee in the cockpit, evenings under a sky with no porch light competing with the stars. This is the antidote to a summer that's starting to feel like it's slipping by unremembered.

On the water: Commanding a 30'–45' auxiliary sloop on a multi-day cruise: provisioning, boat systems, advanced sail trim, anchoring and mooring, docking, and emergency operations. Prerequisites: ASA 101 & 103.

ASA 105 · COASTAL NAVIGATION

Read the Water Like a Story

Charts, bearings, dead reckoning — it's the rare classroom where "when will I ever use this" has an obvious, immediate, on-the-water answer.

Ashore & aboard: Reading nautical charts, tide and current tables, plotting positions, correcting for current and leeway, and planning safe coastal passages.

Four sailors belowdecks consulting a chart as the Captain indicates their position
ASA 116 · DINGHY & OUTBOARD ENDORSEMENT

Little Boat, Big Confidence

Sometimes the biggest win is driving a dinghy from the boat to the shore.

On the water: Safe dinghy and outboard operation from a dock, a beach, and a cruising yacht — towing, hoisting, storage, and care of the boat.

ASA 118 · DOCKING ENDORSEMENT

Sticking the Landing

The quiet, satisfying skill nobody brags about until they've nailed it — bringing the boat home intact, under control, no drama at the dock. Every boat owner needs this confidence.

On the water: Docking and undocking technique for single inboard or outboard engines, efficiently and without damage or injury.

From a student who sailed with us

The ASA 103 course that my wife and I took was outstanding! You have a real gem in Captain Frank McKee. His knowledge, experience, approach, and attitude are second to none. This professional mariner ensured that every one of us not only learned the topics of ASA 103, but that we also left with additional skills or knowledge particular to our own situations. He obviously loves what he does, and it shows in the way he tailored his instruction to our different needs and goals. While the sailing instruction was nothing short of exceptional, I learned just as much about leadership and teamwork during our four days on the water with Captain Frank. The students came to this class with widely varying experience and learning styles; he accommodated them all. Thanks for another great course.

Jeff R.
ASA 103 graduate

Taught by the people who actually know the Bay

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

Captain Frank McKee Captain Gary Hutson Captain Julie Tipton Captain Bob Baginski Captain Andrew Seligman
Facebook Logo Instagram Logo YouTube logo

This is the summer to get out on the water.

Reserve your spot before the 2026 season books up. Every class is full-length, hands-on, and led by a Captain who genuinely wants you to fall in love with sailing.