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Jane and Finch - immediate resemblance
Trinity Bellwoods Park area. Stop by Bellwoods Brewery if you guys drink.
Graffiti Alley, Raku - Japanese Udon, Kensington Market, Evergreen Brickworks, Tommy Thompson Park, Centre Island
AGO, ROM, Shoe Museum, Trillium Park. If it was summer there would be more options
North of Brooklyn and Antler for restos
Lawn at Budweiser Stage if there is a good concert
St. Lawrence Market for lunch, then take a stroll over to the Distillery District. And if you can swing it, catching a show at the Four Seasons Centre would be amazing. That's a classic Toronto experience right there. Have fun!