Awesome things to do and eat in Toronto?

Lots to see and do especially for a 19 year old! On a weekend I'd recommend a walk through Kensington Market to check out the street art, vintage and second hand shops. Food in Kensington is good wherever you go but grab a beer at Ronnie's Local 069 and order a grilled cheese - they walk your order across the street from The Grilled Cheese. You can check out the infamous CN Tower and while you're in the area visit the Steam Whistle Brewing for a tour and a taste of the local brew. Close by is also the Distillery District and St. Lawrence Market two things not to miss in T.O. If live music is of interest Lee's Palace in the The Annex always has great shows and the neighbourhood is full of college kids getting beer at The Brunswick House and plentiful cheap sushi places like New Generation Sushi. If you plan on doing any shopping, skip the Eaton Centre and head over to Queen Street West it spans the west side of the city and if full of every type of store you could want and the local favourite Trinity - Bellwoods Park where you'll find great up and coming art galleries, book stores, coffee joints and gastro-pubs. Hope you have an awesome time!

Id suggest taking him out to the Real Sports Bar & Grill, voted the best bar in America by ESPN. You are prolly wondering, well Toronto isnt in America. You guessed it! But ESPN didnt, they thought Real Sports Bar and Grill was in fact in Michigan and was disappointed when they realized they needed a passport to get here. It has one of the largest screens at 400 square feet, and over 200 tvs in the bar. Including urinals. Best bet, take him on a game night when the raptors or leafs play and you get that same in arena excitement without the cost.

http://www.torontosun.com/sports/hockey/2010/09/03/15242761.html

Go to the Distillery district, it may be decorated for the holiday season, which is pretty at night. There's shopping, galleries, restaurants and of course the Mill St Brew Pub . Mill St. Brew Pub

Toronto has tons of beautiful shops and restaurants that are amazing! Check out the Distillery District, Dundas West Station (loads of cool coffee shops), and visit The Monkey's Paw book shop on Dundas West for a really cool take on a book store. They have used and vintage books but the best part is the book vending machine in the back that gives you a mystery book for $2!

For activities you kind of have to do the CN Tower.  It's just one of those touristy things that a visit to Toronto can't be done without.  After that check out blog.to or Toronto.com for the what's happening guide.  There is a a lot of great live music to be had and something for every taste happening almost every night somewhere in the city.  Instead of recommending specific establishments I would recommend some areas to check out.  King St W has a lot of trendy restaurants and bars and a few nightclubs.  Queen St W has the best shopping and a few great rock bars.  Ossington Ave is a great street to bar crawl.  Most of the places are really small, but they are close together and you can stop in and have a drink at each one.  All have a unique character.