How did this topic get so long without me seeing it?
First off, Ski Diva, if you're coming here, we absolutely must meet up! When are you planning to visit?
There's some great advice in this thread. I'll just add a few items:
Transport: You can get yourself an unlimited
one-day or three-day pass for public transit. The metro is very easy to navigate and useful for just about anywhere of tourist interest where you can't walk. Check out
https://www.stm.info/ for more info. Agree with everyone to avoid driving unless you absolutely have to. I have a car but I never drive unless I'm leaving the city. It's just not worth the headaches. Oh, and if you like to cycle, free bike rentals are available from the tourism booth outside Metro Mont-Royal on a first-come, first-serve basis during the summer and early fall.
Places to stay: We have all the usual business and chain hotels, sure. But if you're looking for something a bit more unique, book into a
Gite (B&B) or an Auberge - a lot of them are privately-owned in Victorian triplexes in the Plateau or Quartier Latin areas, which are ideally located for walking around, but will be cozier and friendlier than a Sheraton or a Marriott. Staying in Old Montreal can be a bit pricier, though there's a budget-friendly hostel or two down that way. It's charming, sure, but it has some drawbacks - you're a bit further walk from most of the action, and it can be pretty dead in the wintertime. Nice in summer, though.
Restaurants: Tourist standards include La Banquise (poutine), Schwartz's (smoked meat), St-Viateur Bagels, Gibby's (expensive steakhouse in Old Montreal), etc. I highly recommend a nice leisurely weekend brunch at a favourite spot like Avenue (Plateau) or Le Cartet (Old Montreal). If you're vegetarian or vegan, try Chu Chai or Aux Vivres. Santropol is awesome for sandwiches and soups in the winter. Cactus is great for Mexican food. Some of the associations will be obvious - Chinatown for Chinese food (Beijing is a good spot) or Little Italy for Italian. Prince-Arthur is a pedestrian-only cobblestone street with a bunch of mediocre-food-but-nice-atmosphere restaurants - mostly Greek. Duluth street has a nice similar selection of French and Portuguese spots. Look for "Apportez Votre Vin" (bring your own wine) signs on restaurants, which means you can pop into a local SAQ or convenience store and pick up a bottle of wine and take it with you to dinner. Other than that, this is a foodie city, so let me know what kind of food you like and I'll give you a list of some of my favourites.
Things to do: Depending on what time of year you get here, I'd say don't skip a trip up to Little Italy and Jean-Talon Market - especially nice in fall when the apples are out. Montreal has a ton of
festivals, most of which take place in the summer but there's something happening year-round. Definitely head to Mount Royal, especially on a nice Sunday for the
tam tams. If it's your thing, you can head out to the Olympic Stadium for the Botanical Gardens or the views from the tower, or even a Montreal Impact game. (Habs games, on the other hand, once they're in season, are near-impossible to get tickets for... you're best off just heading to a pub when the game is on to watch on the big screens with other fans. I recommend Cage aux Sports - great atmosphere - or Olde Orchard - better food. But it's off-season right now anyway.) We have culture in the form of lots of museums - the Fine Arts Museum has a Jean-Paul Gaultier exhibit going on right now - and there's the symphony orchestra at Place des Arts, and a great theatre scene in French and to a lesser degree in English. Or, skip the detailed planning and just wander around - Montreal is very walkable and you can take in most of the major things to see just by walking around.
Shopping: Downtown/Ste-Catherine Street is where you'll find all the big department and chain stores that you see pretty much everywhere in North America (with a few strip clubs thrown in... hey, it is Montreal after all). For more indie or unique shopping, you have to get out of downtown a bit. The Plateau (my neighbourhood) is great for this. Just take the metro up to Mont-Royal and start walking east.
Nightlife: Depends on your preferences, again. Crescent and St-Denis have lots of pubs. The English/French divide for those two was more true in the past, but these days not so much anymore... though more UQAM students still hang out in the Latin Quarter and more Concordia students hang out on Crescent. Young crowds on both streets, though it depends where you go. St-Laurent has clubs. If you like microbrews, check out Dieu du Ciel on Laurier or Amere a Boire on St-Denis. There are lots of wine bars in the Plateau along Mont-Royal. Cinq-a-sept (sort of like happy hour but more upscale) places abound near the business areas and in Old Montreal west of the port. The music scene is diverse and full of everything from folk sessions at pubs to indie and underground stuff - and of course jazz, lots of it. Pick up a free copy of the
Montreal Mirror when you get here for listings.
Other stuff: Check out the Montreal Mirror's annual
Best of Montreal reader poll for 2011. Lots of good suggestions in there, especially for
restaurants.
But most importantly - PM me and let me know details of your trip so that we can meet up when you get here.