I was in Montreal for five nights last year, not as a tourist. I was moving my son into an apartment, which involved a certain amount of shopping and moving furniture. I had a car and got to see a variety of neighborhoods.
Montreal is a fascinating and surprisingly shabby city. Even in the summer, you can feel the toll the long damp winter cold takes on the streets and buildings.
With its French and American roots comes disparate communities: Various degrees of French-speaking, Haitian, Moroccan, West African, Vietnamese, and Hasidic.
Eating can be very expensive. Just buying produce can set you back. The famous dish of poutine owes part of its popularity to the fact that it 's cheap. There is one place to go for poutine that is tremendously popular, La Banquise, where you can expect a wait to get in. We didn’t wait and went to another famous place, Greenspot, where it was dreadful. (it is currently ranked 3rd in the Time Out guide to poutine in Motreal). The parks in Montreal usually have seating and tables so you can gather and eat outside. We got carryout and ate in a park at about 11pm.
In the stores you will find that as much produce as possible is Canadian. The stores themselves are Canadian. It is not an extension of the US! Dairy is excellent, and raw milk cheese is available in the markets.
The Hasidic community in Mile End is fascinating. St Viateur for bagels is famous. A must. There are two locations about two blocks from each other on St Viatuer. There is also a very good bakery, Boulangerie Cheskie. Ask for what’s right on the back counter, usually unmarked. Nearby, Cafe Depanneur has musicians all day long (usually a guy with a guitar singing in both French and English) and serves an excellent macchiato. Go into a bank, and you will see quite the scene of Hasidim transacting business. It is a sight.
Go to a friperie, a thrift shop. I went to the Friperie Renassiance Verdun, but there are others. Verdun is an interesting neighborhood with a pedestrianized street. Notice on the side streets the houses have twisting, turning metal staircases on the outside so you can walk directly up to a separate residence on the second floor, typical for Montreal. These are treacherous in winter!
I posted on HO about my eating experiences which included all the communities I named above. It was a mixed bag, and even places that look dirt cheap are surprisingly costly:
The most touristic thing to do , I hated. Vieux Montreal is not that nice, and it is lousy with tourists. It is mostly one long street. I found the whole scene repulsive.
Walking up the Grand Staircase of Mont Royal is a fun activity. It’s 537 stairs. It took me about fifteen minutes with a lot of stopping, especially to take pictures. The St Joseph Oratory of Mont Royal is an unusual site, YMMV. Despite the looks from the outside, it is modern inside.
The Botanic Gardens are vast. The arboretum alone would take a long time to see with many groves of trees you might not otherwise see in the States. The Alpine Garden is my favorite spot. Not far from there, the Hochelaga neighborhood is the most French-speaking neighborhood of Montreal.
Quebec City, specifically the Old Town, is one of the most beautiful cities of the world. I spent a week there, twice. The best thing I ate were the croissants at Chez Temporel. I think you can get them all day. So many beautiful streets to wander, great for kids too. During the summer there is an explosion of activity, especially buskers. I would go in August rather than September. Or if you stradle the two months, go to Quebec City first because the activity will die down in September.