Montreal:
- Most people I know swear by 'La Banquise' for poutine, but to be honest I have never been there. I eat poutine at the dirtiest joints.
- People will recommend 'Schwartz's' for smoked meat, I say **** them, go literally across the street to 'The Main' for less touristy crowd, nicer service, equally good smoked meat.
- Au Pied de Cochon, Garde Manger. Café Ferreira and Holder are also good.
- I would steer clear of Queue de Cheval, and Gibby's, the two most recommended and overrated places in Mtl. (hint, if you want steak, Mtl is not really the place to have it). Also avoid Crescent street, it's a ****ing lame tourist trap.
- Notre-Dame Basilica and St-Joseph's Oratory for obligatory "large religious structures". Great View at the Oratory.
- go up mont royal, great view.
- two great markets (mostly local produce, but also some good places that do lunch right there), depending where you are located (Jean-talon and Atwater).
- Montreal has two seasons: Winter and summer. The woman dress according to those extremes (skidoo suits/full length North Face coats in the winter, next to nothing in the summer).
- Shopping: there is lots of it.
- If you have kids or are a nerd, there are a ton of wicked "museums". Down at the "waterfront" (river), there is a cool science museum, not too far away there is a planetarium too. You can hop over to Ile Notre Dame to visit Parc Jean Drapeau and the Biosphere. The Bidome, botanical gardens and Insectarium are all cool too.
- Be prepared for walking, Mtl has one of the most walkable downtowns going. Might even be worth your while to ride the Metro (subway). It's not really hard to do, and it's nice. However, there is also the option to use BIXI! This is a public bike service, so if it's a nice day, that might be the prime way to travel around. You will see them everywhere (the bike kiosks).
- Always shows going on. Family stuff at Place-des-Arts, or you could just check "The Mirror" to see if any bands are playing at one of the bazillion awesome clubs (if that's your thing).
- Speaking of which, too bad it's in June, Osheaga is always a good time (end of July).
If you have questions, google any of what I just said, Im certain there are websites for it all.
Also, not sure how you are getting in, or where you are staying, but I recommend staying within Centre-Ville (downtown), which is NOT near the airport.
Source: I lived there for 5 years, and visit routinely for work.