Where have you traveled to?
I'll start regionally. I've been to a lot of places in Ontario so there's no point in listing them all. My favourite trips in Ontario are to Tobermory Ontario, Grand Bend/Wassagua, and the drive from Toronto to Ottawa.
Tobermory is in the Bruce Pennisula. It's very beautiful and a wonderful place to camp. There's a place there called the Grotto, in Bruce Pennisula National Park. The water is damn cold but it looks like this
http://www.edto.net/photo_grotto.htm. Just a beautiful place to swim. It feels like someone dropped a rock formation from the Carribean smack in the middle of Northern Ontario.
Grand Bend/Wassagua are two resort towns on Lake Huron. There are a ton of fun for the party scene, and it's some of the best swimming in Ontario. You can walk out for about a mile before the water even gets over your shoulders. The waves get large to, so there's some great boogie boarding to be had.
I've done the drive to Toronto to Ottawa more times then I can count, but it never gets old. At about Kingston all the rolling farmland gives away to the Canadian shield rising up out of the ground. It's really beautiful. Along the way there are tons of great campgrounds to stop in. I like the ones along the St. Lawrence River near 1000 Islands. You can get camping spots right beside the river. Nothing like waking up in the morning and jumping in for a swim right away (I wouldn't recomend it for weak swimmers though, the current is strong).
http://www.visit1000islands.com/visitorinfo/
In Canada, I've been to Montreal on a few separate occasions. It's a great city. I highly recommend to go see a Canadiens game when you're there. The Canadiens have a fan base like no other. Everyone from the plantinum season ticket holders to the guys selling brochures gets wild and crazy.
Quebec City is much cooler if you like history. Old Quebec city is beautiful. I haven't been in many years. I'd like to go back to explore some more.
Prince Edward Island is pretty, but on the slow side. You can explore the whole island in about three days. I was there for two weeks

. The swimming isn't great either since the Atlantic is so cold. The side with the channel between PEI and New Brunswick is a little better temperature wise.
I spent a whole of 7 hours in Winnipeg so I can't comment much on it. If you ever find yourself in the Winnipeg airport, find the upstairs "captain's" lounge. You can sit and watch the planes land, and listen to the chatter from the control tower. Interesting way to spend a layover.
Saskatoon surprised me. I was expecting a fairly boring prairie town. But it was a nice little town. Plus looking out on the wideness of the prairies was a shock I didn't expect. When they say you can see for miles and miles, they aren't kidding. I definitely didn't like the bugs. I have never been so bitten by mosquitos in my life!
I have been all through the US. In fact there are only two eastern seaboard states that I have not been to; Rhode Island and Delaware. City wise, I have been to Detroit, NYC, Miami, Orlando, San Francisco, Washington DC, Philadelphia, Buffalo, Knoxville, and Savannah. Savannah was a pretty interesting experience since we got there on St. Patty's Day

.
I've spent three weeks in France the summer before grade 12. I spent two of them in Paris and 1 in the South of France, in a small town just outside of Toulon.
About 4 years ago I spent just over two weeks backpacking Costa Rica. It was an intensely physical trip. Everyday I was going on ziplines or treking through the rainforest.
2 years ago I did an all inclusive trip to the Dominican Republic. More on that below.
What are your next travel plans?
At the end of April I'm headed to Europe to do the backpacking thing. I'll be there for just under three weeks and I'll be making my way to Amsterdam, Berlin, Prague, Munich, Paris, and Bruges. I am SUPER excited. I think I'm most excited to see Prague at this point. I'm definitely looking for some things to do and see that are off the beaten path.
I'm also planning to head to Vancouver or NYC at the end of August. I can't decide at this point. I have been to NYC before but it was for work so I didn't really get to see or do a lot. I really want to go to MOMA. But I know I will spend so much money shopping if I go there. If I go to Vancouver it won't be so bad. Plus I want to go to Tofino and surf. I tried it for the first time in Costa Rica and I loved it.
Best travel experience?
I have very good memories of Paris and France in general. I love how in France that history isn't torn down or hidden the way it is in Toronto. In Paris, you can see investment bankers strolling down a street where there are still bullet holes in the buildings from WWII. That was so incredible to me.
Worst travel experience?
Hands down, the Dominican republic. I'm the type of traveller who likes to go out and do things-go to museums, go shopping, try different restaurants, etc. I should have known better than to think that sitting in a resort for a week would have been fun. I was bored to tears by the end of it. Even with the free booze

. The only good part was that I got to fufill a lifelong wish to ride a horse at full gallop through the surf. That was pretty badass. I've never done something so thrilling.
Tell us about your top 3 dream destinations/vacations.
The big three on my travel list are
Southern Africa-particularly this trip
http://www.gapadventures.com/trips/southern-africa-adventure/DLLC/2010/
Australia
The British Isles-Gotta visit the homeland soon, me thinks.