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This area houses Toronto's most upscale shopping and has many little boutiques and galleries, so it can be nice to plan an afternoon of shopping before or after a meal on one of the patios in the area. 

Hemingway's:  This is the most popular patio in Yorkville.  It has patios on the sidewalk at the front, and two separate rooftop patios.  But the main, larger roof patio at the back ((which itself has two levels) is the place to be.  Tables here are densely packed together, and some nights it is hard to move, but other nights it's only moderately busy and you get a really relaxing evening.   The food is really just average pub food, but it's fine.  This is really more of beers and 'appies' place to hang out with friends.  The atmosphere is buzzy and fun, and the patio overlooks a very quaint, narrow pedestrian laneway (Old York Lane) with boutique stores.  It fronts on Cumberland Ave.

Dimmi:  Attached to Hemingway's, but unrelated, this Italian restaurant has much better food.  It has a small streetfront patio off the sidewalk. (Its roof is Hemingways.)  However the length of this restaurant is along Old York Lane.  It throws its french doors open at the side, so the patrons inside still get open air, and they are facing that nice pedestrian-only laneway, with no cars visible at all, just cute boutiques, so it really is very pleasant.  

Remy's:  On the other side of the Old York Lane from Hemingway's/Dimmi, is Remy's which fronts on Yorkville Ave.   The interiors of this place are really '80's, but the roof patio is huge and the food is arguably better than Hemingway's (although still pubby).  The roof patio basically looks at the Hemingway's roof patio.  For some reason this place is way less popular than Hemingway's, so sometimes if you really want a Yorkville rooftop, but don't want to wait in a line for Hemingway's, you'll just go to Remy's.

Amber:  Right next to Remy's on Yorkville Ave., and down some stairs, is Amber, which is a more upscale martini bar.  It has much more expensive food, and much more pricey drinks (but the martinis are very strong!).  The inside room is extremely tiny and dark, but the back patio, which runs along Old York Lane, is very nice.  Sometimes they make it look very white linen/South Beath, sometimes it looks very Moroccan, but the crowd always looks the same...svelte glamazons and metrosexuals.   This is more of a drinky lounge place. 

Cafe Nervosa:  Also on Yorkville Ave., at the corner of Yorkville and Bellair, this is a very cool two level Italian place.  It has a great sidewalk cafe, but it also has a great rooftop patio.  Both patios overlook the cute little shops on Bellair, and the steady stream of beautiful Yorkville shoppers and the odd Lamborghini.  The roof patio is a great place to have a meal and wine as the sun sets.  There is also a third patio--a tiny balcony with ONE table for two, just over the door.   Totally romantic.  The food is good too; there is a great cappellini with goat cheese and sundried tomatoes, and an amazing chicken salad that is huge and delicious.

The Coffee Mill:  An old-fashioned Hungarian cafe, a bit out of the way on the bottom level at 120 Cumberland, it has a lovely enclosed patio that's great for coffee and dessert, and people-watching. The Coffee Mill serves terrific schnitzel, goulash and Central European desserts, and attracts an older crowd of Eastern European immigrants. The charming older waitresses have accents and hairdos as thick as the goulash.

The Pilot:  One of the oldest pubs in Yorkville, and still one of the best kept secrets, the Pilot is an awesome bar that has live jazz on Sundays and karaoke nights on the first floor, hosts literary readings and other cultural events on the second floor, and has an amazing rooftop patio that is relaxing and never totally packed.  Many people from the local film industry hang out here a lot (locals, not celebrities).  It has great burgers and pad thai.

The Bedford Academy:  On the west side of Avenue Rd. (which is like the western border of Yorkvillle), right next the Park Hyatt hotel, there is a street called Prince Arthur.  It is a gorgeous tree lined street, with a collection of really good restaurants that aren't in the direct line of fire for tourists, but many locals go to this area.  The Bedford Academy is in a turreted Victorian building, and eating on the patio at front, under the trees of Prince Arthur, is very nice.  There's also a large back patio, but not so nice.

The Duke of York:  Across the street from Bedford, this pub has a great back patio, with lots of tree cover, and very decent pub food.

The Rebel House:  It's not really in Yorkville, it's one subway stop north, on Yonge St. at Rosedale subway station, but it's a favorite patio and it's closest to Yorkville.  It is a Canadian tavern, and is packed with locals from nearby Rosedale and Yorkville.  It has amazing brunch (the rebellion eggs with salmon or the rebel melt are awesome) and for dinner it has a spectacular meatloaf with oniony mashed potatoes.  The back patio is a perfect size and they often put up a big yellow parachute like a circus tent.  This is one of the best places in Toronto.  It's often packed too, especially for brunch. 

7 West:  This is just south of Yorkville, one block south of Bloor on Charles St. Worth mentioning because it is open 24 hours.  It is in a cool Victorian house, and each of the three floors is decorated slightly differently.  it has a tiny front patio and an equally small back patio on the fire escape.  The view is not great, but it's just the kind of urban oasis that's perfect after a movie at the Varsity around the corner, or at 3 a.m. after a night of partying.

Wish:  South of Bloor, also on Charles St., but just east of Yonge.  It's a funky, cool, tiny restaurant with delicious food, and is more of a trendy, fancy place than 7 West.  The patio on the sidewalk is very South Beach, with white curtains, a fountain, and a couch.  Awesome cocktails and good desserts too.  

The Annex

The Annex is a neighbourhoody section with some cute stores and restaurants, and its a few subway stops west of Yorkville on Bloor (between Spadina and Bathurst stops).  But people come here for brunches a lot.

By the Way Cafe: A mostly covered patio at the central corner of the Annex - Bloor and Brunswick.  This is a great place to sit with a giant latte in the morning or a beers at night, and watch the world go by. The menu here is mostly middle-eastern, though a bit pricey for the kind of unpretentious neighbourhood joint this is, but the omelettes at weekend brunch are yummy, and the vibe is relaxed.

Future Bakery: A student favourite with a huge patio, right across the street from By the Way. Hearty Ukrainian food, desserts are plentiful but uninspired.

Dooney's:  One of the neighbourhood's mainstays - a friendly cafe frequented by the many writers, journalists and artists who live in the Annex.  It has a rustic Italian menu, a very popular (though, truth be told, somewhat mediocre) brunch, and a lovely tree-lined patio.

Kilgour's:  Right across from Dooney's, kind of a laid-back rock'n'roll atmosphere, with a menu of more or less basic pub food.

Paupers Pub:  A pub in a great old bank building, with a side patio and a roof patio. Great vibe and a good selection of beers, but don't come for dinner -- the food is bland and greasy.

Victory Cafe:  In Mirvish Village, on Markham Street, one block south of Bloor. Part of the wrap-around patio is under some huge, leafy trees. The Victory is a favorite haunt of local artists, writers and other dedicated beer drinkers.

The Butler's Pantry:  For really delicious, healthy and surprisingly cheap food, the Butler's Pantry -- also on Markham St. -- is great.  It also has  an amazing home-made salad dressing. Patio out front gives a good perspective on Mirvish Village. 

Boulevard Cafe: On the edge of the South Annex, at Harbord and Lippincott (one block east of Bathurst), this is a longtime local favourite, with a South American menu. Sit in this neighbourhood oasis, sip sangria, and enjoy this leafy, secluded  oasis.

Little Italy 

Bar Italia: a front patio that's ingeniously hidden under the roof -- half-in, half-out -- which works nicely in the rain. Good pasta and panini menu, excellent espresso, good brunch.

Utopia: A heated back patio and an ingenious non-Italian menu:  burritos with various fillings, including lots of vegetarian options, great burgers, etc. Highly recommended.

Cafe Diplomatico (AKA the Dip): The original -- the first cafe in the neighbourhood, back when it was almost exclusively Italian. The patio is huge and always packed on summer nights. The food is simple -- cheap, no frills pasta and Italian standards. Nothing to write home about, but the price is right.

Langolino: A bit hidden, on Clinton St., a couple of doors up from College, across the street from the Dip. A great place to get away from the bustle of College St., with a straightfoward Italian menu and gracious hosts.

Sicilian Ice Cream:  Nice patio, always packed. Ice cream? So-so. The sundaes and floats are too sweet.

The Distillery District

The Distillery District is a gorgeous area of 19th-century warehouses that have been restored and redeveloped, and is now a pedestrian-only zone filled with unique art galleries, boutiques and theatres.  It's truly a beautiful little area with cobblestone streets and lovely Victorian buildings. All the restaurants have patio spaces on cobblestone, and it's one of the best places to eat outdoors in Toronto. 

The  Boiler House:  A fine-dining menu, live jazz, and a phenomenal brunch buffet on Sundays.  

Archeo: Cheaper, and Italian - apps, pizza, panini.

Pure Spirits Oyster Bar: Oysters and other entrees.  Delicious, a bit pricey. 

Balzac's Coffee:  As the name suggests, a coffee house. One of the loveliest in town. You must peek in, even if you want to sip your coffee on the patio overlooking the main square of the distillery district.  

El Catrin: An awesome large patio for excellent Mexican tapas.  The drinks are delicious with a wide array choices.  Though a bit pricey, the atmosphere and the quality of food are worth the extra few pesos!

Baldwin Street

This is one of Toronto's hidden treasures.  It's a two-block stretch of restaurants and shops in an otherwise residential area, between McCaul and Beverley streets, north of the AGO, west of the hospital district, east of Spadina.  This this tiny stretch is jampacked with a cluster of amazing, diverse restaurants with style, character and great food.

Cafe La Gaffe:  A perfect little cafe.  Awesome food, cute decor, tiny front patio which absorbs the beauty and relaxed quirky cool vibe of  Baldwin.

Margarita's Fiesta Room:  Cute little Mexican place with great little patio.  The food isn't always amazing, but the drinks are.

Bodega: A French bistro on the corner of Baldwin and Henry streets.  One of the pricier joints on the block, but a great place to have lunch or dinner al fresco. 

John's Italian Cafe: A longtime local favourite, with thin-crust pizza and simple pastas. Come for a slice and a Limonata at lunchtime. But don't expect anything fancy here. 

King West

At the corner of King and Spadina, there is a proliferation of cool clubs and restaurants.   (This is not the tacky Entertainment District/Clubland, which is just east a little bit and filled with big box nightclubs and corporate patios like Milestone's and Montana's.)  King and Spadina has cool one-off places with some of the best chefs in Canada.

Brassaii:  This place is set back from the street; you have to walk down a brick courtyard to get to the restaurant.  The menu is smallish but  good, and the weekend brunch is one of the best in the area. The interior is totally stripped-down glam New York loft, and very chic.  

Crush:  A nice,  expensive restaurant, whose patio shares the courtyard with Brassaii. 

Susur:  This is sometimes called the best restaurant in Canada, and the chef, Susur Lee, is certainly one of the most famous.  His restaurant is awesome, but also very expensive.  A tasting menu dinner will cost about $120 per person without wine.

Lee:  Next door to his flagship Susur, he has now opened Lee, with a cheaper, tapas style menu.  Have the Singapore Slaw as one of your items!  Sidewalk patio.

Thuet:  Next door to Susur Lee's two restos, another Canadian celebrity chef, Marc Thuet, runs a bistro/bakery that is open for lunch and dinner, with a sidewalk patio. Many think his bread and croissants are the best in the city, and the menu is rich and hearty. Unfortunately, service can be snooty and downright rude. But the place is always packed for Sunday brunch, so line up early.   

Queen West and West Queen West

The stretch on Queen, between University and Bathurst is referred to as Queen West.  The stretch between University and Spadina is now essentially an outdoor mall, filled with midmarket chains like Gap and FCUK, with a few interesting boutique stores that have managed to survive.  It is pleasant and fun and quite touristy.  Spadina to Bathurst is a bit more edgy, with the Bovine -- a nightclub that was the height of urban cool in the 90s -- still hanging on. West Queen West starts at Bathurst and runs west until Dufferin.  It is much more interesting, with business ranging from cool and expensive one-off furniture stores, to boutiques run by local fashion designers, to really old little stores that sell curios.  This is also the art gallery district, especially towards the west end of the stretch.

Ultra Supperclub:  On Queen West, this is a luxe restaurant/bar.  The restaurant has no sign on the street, just these tall carved wooden doors that you go through, and down this little alleyway to get to the restaurant. The rooftop patio is stunning, decked out in white like a South Beach place (for a true Delano rip-off, go the C-Lounge patio on Wellington) and they have delicious mojitos!  Food inside is expensive and delicious, but the patio sometimes has a different menu.

The Black Bull:  This place is a Toronto institution.  Right on a corner in the middle of Queen West, the bar was a biker bar, but now the big patio is filled with everybody and there's always a lineup.  Food is strictly greasy pub.

The Drake Hotel:  This is the heart of West Queen West, currently Toronto's hippest neighbourhood.  The Drake was for a long time a decrepit flophouse, until it was completely gutted and renovated in the mid-'00s.   There is a nice restaurant inside, a lounge/bar that is always packed, a downstairs performance space and, a cafe with a sidewalk patio.  But the key feature is the upstairs rooftop Sky Yard, which is a great patio space.  You could eat from a less expensive menu on the patio and enjoy the night.  Unfortunately, it has become so popular that there is often a waiting list to get on the patio.

The Beaconsfield:  Right next to the Drake is a very nice pub in an old bank building, with a sidewalk patio.  It is very beautiful under a big tree, and always packed in the summer.  Lots of buzz and energy between this place and the Drake.  The food here is excellent too --  fancier than standard pub fare.

Entertainment District

The King St. restaurant strip between John and Peter is popular with tourists and theatre-goers, but the the dining experience is kind of touristy and mediocre. Urban has a lovely rooftop patio, but the food is overpriced and decidedly average. St. Tropez is a French bistro with a romantic back patio that's probably the best bet on the block.

The Fifth:  An expensive steakhouse with a rooftop patio. Take an industrial elevator to this elegant hideaway, and drop a few hundred bucks on dinner. The patio is beautiful; the restaurant gets mixed reviews.