Like New York, Montreal is eminently walkable, and it has an excellent metro system, and easy to hail cabs. Dining and shopping, as you would expect, are excellent, and, even with the Canadian dollar moving back towards par with the US dollar, still a good deal cheaper. Ditto for hotel rooms. Of course, it also has the unique appeal of being the world's most important French-speaking metropolis outside Paris, and has a distinctly un-Anglo-Saxon character, a refreshing change from Ottawa (where I live) or Toronto (which I have never really taken a fancy to, despite its many attractions).
Also, like New York, and like all great cities indeed, Montreal is a city of neighbourhoods, cheek by jowl, but yet each distinct, offering its own particular brand of urban interest. Downtown is the area that most tourists know, and stick to. The old port area by the river has also become rather touristy as of late. But for me the real interest lies in the area where "+" marks the spot, the intersection of Sherbrooke, the main east-west drag, and St. Laurent, the main north-south one, that, in fact, divided the city into the traditionally English-speaking and French-speaking zones, west and east of St. Laurent, respectively. While this is more myth than reality nowadays, with Anglophones and Francophones living on both sides of the putative divide, it's not entirely wrong. Look at the election map: the constituency just west of St. Laurent votes Liberal, and just east Bloc Quebecois (in fact, it's the seat of the party's leader). From this intersection, you can walk up St. Laurent, or the "Main" in Montreal slang, the old Jewish main street of the city (made most famous by Mordechai Richler). Most of the old establishments are gone, replaced by hip and trendy restaurants and nightspots. My favourite, Buonanotte, entices you in with a gaggle of waitresses who look and dress like runway models (I'm not complaining, by the way), but backs it up with superb food and a deep wine list. More like Europe than Anglo-America, it's both a fine dining establishment in the early evening and then happening nightspot into the wee hours. (If you're there after midnight, by the way, and have a large enough group, go for the bottle service in the VIP lounge area. $200 for a fifth bottle of Grey Goose, split five or six ways, works out much cheaper than individual drinks.) If you go further up the street, into the former Little Italy, you can try Casa Napoletana, or Bottega, for authentic wood-burning-oven pizza.
Go further east, to St. Denis, and walk across Mont-Royal, and you're in the heart of the Plateau, the traditional centre for French-speaking intellecual life in the city. It's where most of the Francophone writers, filmmakers, artists, and so forth live. It has a laid back, bohemian character, a little bit like the Village in New York, that's in marked contrast to the glitz and glamour of the Main. Connecting these two neighbourhoods are interesting cross-streets, such as Prince Arthur, a pedestrian-only thoroughfare with some interesting cafes. The most interesting new arrival is Marche 27, on Prince Arthur, just west of St. Laurent. Step in here, and you feel like you're dining in the Village, or maybe Nolita. Head south down St. Denis, as the street slopes steeply down towards the river, and you get into the Latin Quarter, another packed with restaurants and bars, many catering to the university students at UQAM nearby. And all of this is just scratching the surface of potentially interesting neighbourhoods to visit, walk around in, and dine and shop in.
All of this ... just two hours' drive from Ottawa, the civil servants' town that fun forgot? It feels more like jumping into a transporter a la "Star Trek" and winding up on an alien planet!
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