Street
The thing for me is preparation:
Bike Prep - Tyres, fluid levels, light operation (headlight, tail light, brake light, indicators (flashers)), chain etc
I normally only ride every couple of weeks, but for medium to long distances, 300 - 700km's (200 - 400 miles (ish), so after each ride the bike gets a wash, which is a good opportunity to also give it a good check over, and any adjustments made, bits lubed.
Self prep - staying in shape is important, for the body and the mind.
I also read as much as I can about motorcycling, the why's and why nots. As with any information, some is valuable, some is not. The hardest part is figuring out which is which!
Ride prep - this will depend on where I'm going, and who I am going with.
I often ride with a few buddies and we know each other well. There are no egos, and we don't talk about who's fastest or slowest - we just enjoy each others company.
Everyone does their own thing, and although we don't break any land speed records, we certainly cover some distance in good time (making progress).
We always discuss where we are going, what route we are taking and where we will be stopping during the ride.
Things change when riders I haven't ridden with at all, or often, are involved.
If someone comes with us, we always take care to explain the above and make sure they 'get it' (in terms of route, stops etc).
We also keep an eye on their riding, as we don't want 'incidents' to occur, and if we don't feel that they fit well, we don't invite them again.
This may sound a bit pompous, but as I said, we know each other well and trust each others abilities, I feel this is important when riding with others.
If I am by myself, then depending on where I am going, conditions etc, it's a good opportunity to practice.
Throttle control, turn in, lines, SR's, even road etiquette - but you have to pick your times.
If I'm heading somewhere remote, I always give my wife a timeframe when I will contact her, and of course explain where I'm heading to, and more importantly, which route I'm taking to get there. Very rarely will I deviate from this plan unless something unexpected happens. And if it does I will normally text her so she knows.
There are a lot of country roads around here which are fun and lead to magnificant destinations, but sometimes there is very little traffic flow, so peolpe need to know where to look if things go bad.
Most importantly, it's about having an adventure, and that's what makes it so much fun!