CANADA- ON
Torontonians please feel free to add to this...! 
GETTING HERE:
If you're staying downtown, Porter flies into the airport on the Toronto Island. I believe other airlines also fly to this airport now, but Porter has great service. (Complimentary wifi, coffee, tea, water, snacks, beer, sandwiches... cute flight attendants.)
https://www.flyporter.com
GETTING AROUND:
Airport Limo: (416) 820-8300
www.torontoairportlimo.com
Always on time! Book easily online, and they will text you when they arrive. Comparable in price to a taxi.
Beck Taxi: 416.751.5555
Escort approved! 
Or if you're feeling more thrifty...
Express Bus to Pearson Airport:
1-800-387-6787
http://www.torontoairportexpress.com
Cheap! Comfortable! Wifi on board and plugs for your laptop. Many places to catch this bus - Royal York, Delta Chelsea, etc. More info on their website.
Bixi bike rental: https://toronto.bixi.com
No seriously, it's neat.
TTC
Public transit costs $3.00 in cash, tokens are $2.50. Unlimited day pass is a steal @ $10.
http://www3.ttc.ca/Trip_planner/
http://crazedmonkey.com/toronto-transit-map/ (Google map with TTC routes over top. Very helpful.)
WHERE TO STAY:
There is already a post about hotels I think but here are a few...
5 Star:
http://www.thehazeltonhotel.com
http://www.ritzcarlton.com/en/Properties/Toronto/Default.htm
Boutique:
http://www.germaintoronto.com (Two locations, go to the one on Mercer w/ Victor restaurant)
http://www.metropolitan.com/soho (Lovely!)
http://www.gladstonehotel.com/hotel (On the West end. Rooms decorated by artists)
http://www.thedrakehotel.ca
http://www.windsorarmshotel.com
http://www.pantageshotel.com
http://www.thompsonhotels.com/hotels/toronto/thompson-toronto (New-ish!)
Big:
• Hilton: http://www1.hilton.com/en_US/hi/hotel/TORHIHH-Hilton-Toronto-Ontario/index.do
• Sheraton: http://www.sheratontoronto.com/index.html
• Hyatt Regency: http://torontoregency.hyatt.com/hyatt/hotels/index.jsp?null
(The ugliest building in Toronto, used to be a Holiday Inn but now it's a Hyatt.)
• Intercontinental in Yorkville: http://toronto.intercontinental.com
Across from the museum!
• Intercontinental on Front: http://www.torontocentre.intercontinental.com
• Four Seasons: http://www.fourseasons.com/toronto
• Park Hyatt: http://www.parktoronto.hyatt.com/hyatt/hotels/services/maps/index.jsp
Great spa, if you're into that sort of thing...
• Westin Harbour Castle http://www.starwoodhotels.com/westin/property/overview/index.html?propertyID=1084
• Royal York: http://www.fairmont.com/royalyork
Right across from Union Station.
• 1 King West: http://www.onekingwest.com
Located right beside King subway station. If you're here for an extended trip, they offer rooms with small kitchenettes.
FOOD:
I am a foodie so I can suggest some great restaurants... but you'll have to ask me out first.
Torontonians please feel free to add to this list of inside tips!
I especially like the bike rental idea