Montreal (First Day): Landed in Trudeau Airport around mid-day and took 747 bus into city. Next proceeded to walk around Old Montreal / River front area. Enjoyed beautiful interior of Notre Dame Cathedral. Then took Metro to Olympic Park Area, went up in Tower, did tour of Olympic Stadium, and visited the Biodome. After walked around Plateau neighborood. For dinner ate at Au Pied de Cochon, sampling the Poutine with Foie Gras (and brown ale).
Montreal (Second Day): First, the Hop-on, Hop-off tour (first time ever in a city), stopping at St. Joseph's Oratory and Mont-Royal Park, taking in the view at the Chalet. Bus tour also included nice views of Biosphere, Casino, McGill, and others. Next off to Central Station for 4.75 hour train ride to Toronto. Got into Toronto around 9pm. Had a quick poutine dinner at Smokes then off to a club in Toronto's entertainment district.
Toronto (First Day): Started walking North essentially, visiting City Hall, Eaton Center, Ontario Parliament Building, U. of Toronto, and Queens Park. Did Tour of Casa Loma. Then over to Yorkville for a quick stroll before heading to Chinatown (for lunch) and walk through Kensington Market for some counter-culture. Next walked along the lakefront, eventually passing by St. Lawrence Market and a quick stop at the Old Distillery. More Poutine for dinner.
Toronto (Second Day): Started morning by going to Hockey Hall of Fame, then visited the CN tower and did the Edgewalk experience! That was quite a thrill and perfectly clear skies! Then took subway to Pearson for a late afternoon flight back to NYC.
Happy to answer any questions about logistics or sites. Was fun trip, but unseasonably cold for late September.