In October 2025, I untied the dock lines in Picton Harbour, pointed Sweetwater south, and didn’t stop until we reached the turquoise waters of the Exumas. Three thousand nautical miles, one Bavaria 36, and a lifetime of memories later — here’s how it went.
Why We Did It
Happy Sailing had been running courses out of Prince Edward County for years. The waters of Lake Ontario are incredible for learning — predictable winds, sheltered bays, and a sailing season that keeps students coming back every summer. But I always knew the Caribbean was calling.
The idea was simple: sail our own boat down, set up a winter school in the Exumas, and offer liveaboard courses in one of the most beautiful cruising grounds on Earth. The execution was anything but simple.
The Route
We left Picton in mid-October, just as the fall colours were peaking along the shores of Prince Edward County. The route took us:
- Lake Ontario to the Erie Canal — A beautiful inland passage through upstate New York
- Hudson River to New York City — Sailing past the Manhattan skyline at sunrise is something I’ll never forget
- The ICW (Intracoastal Waterway) — Down through New Jersey, the Chesapeake Bay, and into the Carolinas
- Offshore to Florida — Picking our weather windows carefully for the open-water passages
- The Gulf Stream Crossing — From Fort Lauderdale to the Bahamas, riding the current east before turning south
- The Exuma Cays — Threading through the island chain to our new home base
The Hard Parts
I won’t sugarcoat it. There were days when the weather didn’t cooperate, when the engine needed attention in a marina we hadn’t planned on visiting, and when the sheer fatigue of standing watch overnight tested every bit of resolve.
The Gulf Stream crossing was the most intense 24 hours of the trip. The current runs north at 3-4 knots, so you have to aim well south of your target and let the stream carry you. At night, with nothing but stars and the glow of the instruments, you feel very small — and very alive.
The Moments That Made It
For every tough moment, there were ten incredible ones. Dolphins riding our bow wave off the coast of Georgia. Anchoring alone in a creek somewhere in the Chesapeake with nothing but osprey for company. The moment the water changed from Atlantic grey-blue to Bahamian turquoise — you could see it happen almost instantly, like someone flipped a switch.
And then arriving in the Exumas. Dropping anchor in crystal-clear water over white sand, swimming off the back of the boat, and knowing that this is where we’d be teaching. That’s when the whole vision clicked into place.
What It Means for Happy Sailing
That passage wasn’t just a personal adventure — it was the foundation of our Caribbean school. Sweetwater is now both classroom and home. Every student who comes aboard for a 7-Day Skipper course is learning on a boat that’s proven herself across 3,000 miles of ocean.
There’s something powerful about teaching on a vessel with real sea miles under her keel. When I tell students about anchoring techniques, I’m drawing on hundreds of anchorages. When we discuss weather routing, I’ve lived it — staring at GRIB files and making real decisions with real consequences.
Looking Ahead
This winter marks our first full season of Caribbean courses, and the response has been incredible. Students are flying in from across Canada to spend a week learning to sail in paradise. We’re running 7-Day Skipper courses, Mileage Builders, and even catamaran endorsements.
If you’ve ever dreamed of learning to sail in the Caribbean — or if you’ve got your certification and want to build confidence in warm water — come join us. Sweetwater is waiting.
Fair Winds, Evan