I did take a trip to Old Montreal about a month ago. We went to see the debut of the new Cirque du Soleil show, it was at the old port. We stayed at Hotel Nelligan which is a great (but pretty expensive) boutique hotel, right on the main strip. Old Montreal is super nice, lots of cobblestone streets, full of bars and restaurants. We went to a mozzarella bar which was outstanding. We also went back to Schwartz's deli for the best smoked meat sandwich, and La Banquise for the best poutine in Montreal. It was a walking vacation, we walked about 40,000 steps in 2.5 days that we were there, but everything was in walking distance.
One thing that I wasn't a big fan of is the amount of homeless people in the area. I guess it's the same in every big city now, but there were definitely a lot more than the last time I went.
Also we took a trip into downtown Toronto this past weekend, and I had the best hamburger of my life. Aloette at Queen/Spadina, it wasn't cheap ($30 CAD for a burger and fries) but it was 100% worth it. Reservation only, and it books up a month ahead. Probably because it made it to this show:
You HAVE to Try This Burger at Aloette in Toronto | Big Food Bucket List - YouTube