I didn't post here before our trip, but I did do extensive research of existing posts. So I thought I'd report back. My dining companion and I are in our mid-30's, no children, and we live in Boston.
Arrived in Montreal on Thursday evening. Hotel in Old Montreal...couldn't ask for a better location! It was drizzly so we sought shelter and beer at Les 3 Brasseurs. He ordered the 4-beer sampler and then settled on a pint of the amber. I started with a pint of the blonde and then switched to the amber. Nice atmosphere here...a little sports-bar-esque. Food looked uninspired (pizza and sandwiches).
Dinner at Le Bourlingeuer. He ordered the pork with apples, and I ordered the confit of duck. This is a nice little, quiet restaurant. Standard French bistro fare for a very good price (dinner includes soup/salad, entree and dessert). We also ordered half bottle of the house reisling.
Next day we trekked to Schwartz's and bypassed the 20-person line (at 2pm) by getting take-out. Shared a smoked meat sandwich and a wild cherry soda. We took our goods about 6 blocks to a little park (St. Louis Square?) and ate outside. Then we walked over to Meu Meu for some ice cream. He had French Vanilla, I had Raspberry Sorbet. Yum!
Dinner at Aszu. Sat on the terrasse which is behind the restaurant and very cozy. Not very crowded for a Friday night. Shared the octopus and lentil salad. Then we each ordered the Risotto with Venison. A little curious about the "Horse Tartare" but after seeing (and smelling) all of the carriages in Old Montreal, just couldn't consider it. "Deer" seemed like a better option. With a bottle of wine, meal was around $130.
Next day we saved ourselves up for Jean Talon. Got there at around noon and started on the Chowhound tour: fried calamari with spicy mayo, then a ham and cheese crepe, then a spicy sausage with slaw, and finally ice cream. That place is incredible. I am so jealous.
Final dinner at Jardin Nelson (it was raining and we chose it for the ambiance and live music). He had the mushroom crepe (a little too sweet for my taste) and I had the smoked fish salad (nice and light for me).
Overall, we had a fabulous time. I wish Boston had so many outdoor eating and drinking options. The only thing we had trouble finding was a spot to just get coffee and dessert (not ice cream) in the evening. Is it expected that you'll get this in the same place you eat your dinner?