Everything depends on how you plan on doing your tour. How many miles do you plan to ride each, 40, 50, 60, 100, 100+? That determines how good of shape you need to be in before leaving. The more you are use to doing the kind of miles you plan on riding while on tour the easier the tour will be. Like MassiveD said you don't have to train for touring.

Now for winter riding, I live in west central NH and ride outdoors year round. I don't own a car so I have pretty much no other choice than to ride if I'm going to go anywhere. No I don't have internet access at home either, so if I want to get online...I have to ride.

I find that I hate fall riding the most. The temps are such that you can't ever dress like you should dress. Winter is easy to dress for, just keep the layers off and let the heat escape so it doesn't build up and start making you sweat. Sweat is called evaporative cooling for a reason. It's design to cool the body down...if you want to stay warm you want to avoid sweating in the first place. Let the heat escape and you'll stay warm. Winter time that is easy but during the fall when it maybe in the mid 20s in the morning and lower 50s in the afternoon that gets to be a pain in the butt to try to stay dry. The temps rise too much and that causes you to sweat too easily.

Get out on the road and ride and learn as you go. Experience is the best teacher. I will agree, the more hills the better. Don't worry too much about the snow. I did in the beginning for no reason at all...at least up here in NH. I just ride on the snow, not on the wet pavement, and I have no trouble. Just remember, like driving a car, don't make any fast moves...take everything slowly. Fast moves on snow/ice will send you to the pavement quicker than you could ever imagine. Yeah, I had my first snow ride this morning. No accumulation but it was snowing during the beginning of ride. Winter is coming.