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Go to the Mont-Royal Belvedere (free) for great views of the whole city and the South Shore of Montreal - get there by bus. The 11 bus (STM) traverses the mountain from the Mont-Royal metro station and Chemin de la Côte-des-Neiges (bus and subway system is very safe)
For a different view of downtown and a more landscaped park with bits of Expo 67 relics here and there, go to Île Notre-Dame and Île Sainte-Hélène, accessible by métro (yellow line) or, in the summer, by boat that leaves from the Old Port.
Go have a pizza (fav pizzeria Napolitana..bring your own wine..pizza no.29!) & coffee in the Little Italy area (Saint-Laurent between Saint-Zotique and Jean-Talon). At 6862 Saint-Laurent blvd, Milano is a famous family-run Italian grocery store (since 1954). La Bottega offers pizzas exactly as in Naples, baked in seconds in a wood-burning oven imported from Italy, with a large choice of fresh ingredients exclusively. While in this area, if you're in need of ANY kind of spices, Anatole (6 822 Saint-Laurent) is where you need to go.
Go have a stroll in Chinatown (Saint-Laurent - de la Gauchetière - Saint-Urbain)
Head to the biggest open air market: Marché Jean-Talon (subway station Jean-Talon) -- best in summer and the fall, with vegetables, fish, spices, gelatos, and fine products both locally and from around the world. Not to be missed are the Marché des Saveurs, fine cheeses at Fromagerie Hamel, and scrumptuous fresh maple syrup pie at Sucreries de l'érable, next to Ryad and the ATM.
Stroll through the McGill University Campus (downtown - north of McGill College street)
The gay village is quite interesting even if you're not gay, and gets especially lively at night.
Best streets to walk (restaurants, specialty stores, clothing, shoes, books, coffee shops, etc etc): Laurier street between Querbes and Saint-Laurent (luv Juliette & Chocolate for their hot chocolate menu or Baldwin Barmacie for an evening drink), Laurier between Bréboeuf and Papineau, Mont-Royal street between Saint-Urbain and De Lorimier, Saint-Laurent boulevard between Sherbrooke all the way up to Bernard, Saint-Denis boulevard between Sainte-Catherine and Saint-Joseph, Bernard street between Wiseman and Saint-Urbain (stop at the Bilboquet for ice cream, and there are many nice restaurants for $$-$$$), Sainte-Catherine downtown for shopping (including the underground malls) and in the gay village from Berri to Papineau where it is closed to traffic during the summer months
Crescent street is the largest club area, but also the most mainstream and most touristy. Other club areas include Saint-Laurent (chic supper clubs and bars around Sherbrooke, and north of Pine more affordable, and a bit younger and more local), the Latin Quarter (mainly bars and pubs, not really dance clubs, mainly centred on Saint-Denis between de Maisonneuve and Sherbrooke but with a few bars such as Jell-o or Le Cheval Blanc a few blocks east or west along Ontario), Old Montréal (more touristy than local, but with Les 2 Pierrots traditional Québec music bar, plus supper clubs and other hip places), the Village (mostly gay, but all people are welcome), and Le Plateau (mainly local bars, scattered here and there along Saint-Denis, Mont -Royal, or Saint-Laurent in the Mile End district).
BAGELS: 2 favorite places are : the ancestor Fairmount Bagels, established in Montreal in 1919, at 66 Fairmount St East; open 24/24, 7/7 all year around. And St-Viateur Bagel, on Saint-Viateur street then head to cafe Olympico for a coffee (Between Parc avenue and St-Urbain Street)
Smoked meat + Cherry Coke: Schwartz's on Saint-Laurent between Napoleon and Roy E (chaos! quite the experience..cheap..good- Montreal Institution) but if the line is too long, La Main across the street is (according to some) just as good and has a larger menu to boot.
Tender flavourful roast chicken is to be found for dirt cheap almost next door from Schwartz's, at the Portuguese family-run CocoRico ; you may eat on the premises, diner-style, or take-out. Weather permitting, it is possible to eat it outside at a little park a tad further north, across the street from Divan Orange, corner of Saint-Laurent and Rachel St
For shopping "mall style" -> Sainte-Catherine downtown between Stanley and University -- the street is full of shops, and there is a series of underground malls linking Peel and McGill métros. From west to east: Les Cours Mont-Royal, Simon's, Montréal-Trust, Eaton Centre, Ailes de la Mode, Place de la Cathédrale, and the Bay. Plus, via tunnel heading south from Eaton Centre: Place Ville-Marie.