DOWNTOWN. This three-story establishment is an old Victorian house which has been converted into a café frequented by a diverse crowd. The downstairs bar has a hip atmosphere, and the rooftop patio draws a young crowd. Whichever spot you choose to settle down in, rich yet inexpensive desserts will prove to be quite satisfying. If your appetite is a little bigger, you'll also find surprisingly good appetizers, pastas, sandwiches and soups.

WEST TORONTO. The Academy is an upscale pool hall, set in former factory space that was once home to the Brunswick Balke Collender Company, manufacturers of pool tables and accessories. The place has about 20,000 square feet of renovated space divided into several different rooms, each with a different (although equally classy) ambience. Among the numerous pool tables are several hand-carved antiques that were actually built in the factory a hundred years ago. The Academy has an amazing stock of beverages: over 350 wines, 60 grappas, 20 vintage ports, 130 cognacs and over 100 international beers. The food is good, too. Call ahead to confirm hours, as this is a hugely popular spot for private events.

DOWNTOWN. A classically stylish spot, Bar Italia is an attractive little bistro style bar and restaurant that's been a popular neighborhood favorite for years now. Wine is the quaff of choice for most patrons; food options are mostly Italian, with a great selection of appetizers, small plates, sandwiches and main courses. Live music on weekends, too!

DOWNTOWN. Subterranean it may be, but C'est What is definitely not sub-par. Dedicated to all things local, the establishment promotes Toronto with exhibits from regional artists and shows from local musicians in their state-of-the-art performance room/recording studio. Before they made it big, the intimate space hosted Barenaked Ladies, Jeff Buckley and Jewel, among others. An amazing selection of beverages includes their own line of craft brewed beers and wines, an array of Ontario microbrewed beers and wines, plus a great list of whiskies. In keeping with Toronto's rep as a multi-cultural city, the menu features fantastic food from around the world. A true Toronto favorite.

DOWNTOWN. When it opened in the late 1990s, Billiards Digest magazine named the Charlotte Room one of the top ten best new pool rooms in North America. The place has continued to live up to the initial kudos, offering a classy space with several tables and impressive food and beverage menus (no greasy wings and canned Schlitz here!). If the pool tables are occupied or you simply want a break, you'll find a number of other diversions in the form of board games, everything from chess to Boggle to Risk. Some Friday nights host live bands or magic shows.