Originally Posted by
eigenvector
Second the recommendation for Libretto, which I love, but be warned that it does get quite noisy in there. Canoe (in the TD tower) is tops for Financial District dining, but pricey ($50+/person).
Libretto has a patio now, but I agree it does get noisy - it's also always packed during the week, so you need patience to get in.
Canoe is pricey for dining, but it's a great spot just for a drink. Service is very friendly and drink prices are not necessarily higher than in other spots in the area. The view is priceless.
Ki... oh well. They have decent sushi, otherwise, it's a meat market and not a good one IMHO.
Good options for reasonably priced (and good) food are Moxie's on Wellington (even though it's a chain), canteen in the TIFF Bell Lightbox on King, Mercatto and the Gabardine on Bay.
Italian options with reasonable wine prices are Gusto 101 on Portland (and King) or, if you go East, Uncle Tony's on Wellington just East of Yonge. Around the corner from there is Origin with delicious food and a nice patio, if you are inside, don't expect to be able to hold a conversation due to the loud music (same as in Drake 150 that someone else mentioned).
You may want to check out the revitalized harbourfront area. If so, Amsterdam brewhouse is not a bad option, even better if you like craft beer.
I personally like the places out of the direct Union station vicinity better, King/Queen/Dundas West of Bathurst, or East of Church. Ossington has some fun places. A good option a little closer by with a nice patio is the Queen Mother Cafe on Queen, just West of University.