oronto & Cobourg: Walking, Touring, Eating, and Crossing Lake Ontario

Our visit to Toronto started with meeting our friend Bill, who knows the city better than anyone. He also knows something every local learns quickly: don’t bother trying to park downtown. Because of that, Bill walks everywhere — and that meant we walked everywhere too.

A Walking Tour with “Two‑Block Bill”

We spent the better part of the morning on foot. Eventually I asked Bill how much farther we had to go. “Two blocks,” he said. I’m convinced he adds a few extra blocks as a built‑in walking tariff.

Despite the mileage, he was a fantastic guide. We ate well, drank well, and covered more ground than I expected.

Toronto Highlights

Bill took us to the historic hotel where the Queen stayed when she visited Toronto. From there we visited a bar inside the old jail — complete with the same 3‑D tile you’ll find in Venice, Italy, and coincidentally the same tile I have in my shower at home.

We stopped at Eataly for desserts and gelato, then found ourselves at another bar shortly after. Toronto has no shortage of places to sit, sip, and enjoy the city.

CN Tower Views

We made our way to the CN Tower, where the view was spectacular. From the top we could see Pair of Jokers sitting in the harbour — a surreal moment seeing our boat from that height.

When it was time to head back, we took the subway. I reminded Bill that it runs in both directions, which he pretended not to hear.

Toronto gave us a couple of very enjoyable days. For such a large city, it was impressively clean, friendly, and easy to explore.

Crossing to Cobourg

Our next stop was Cobourg, a charming town on the north shore of Lake Ontario. We crossed back over from Toronto and met friends of Bill’s for dinner. They shared helpful information about future stops on our route — the kind of local knowledge you only get from people who know the area well.

Cobourg has an interesting bit of history: at one point, it was almost chosen as the capital of Canada. The town still carries that proud, historic character today.

A clean marina, friendly people, and a relaxing stop on our journey — the perfect way to wrap up this leg of the trip.