I have been riding since 1989. I bought a crappy 250cc cruiser bike to get my permit. Shortly after getting my permit, while I was doing a slow turn, I noticed the front wheel was wobbling. When I stopped and lifted the front to check it out, the front wheel fell off. The bike was mechanically shaky to begin with, but this was the deciding factor. I decided that it was worth the extra cost to get a decent bike; to avoid possibly getting hurt because of mechanical issues.
I scrapped that bike, and purchased a 1988 250cc Kawasaki Ninja. It was a great little bike, especially for a beginning rider. It had enough pep, got great gas mileage, and looked great. I had that bike for several years. The only incident I had with the Ninja was again during a turn. My rider got spooked and counter leaned. I ended up having to lock the front brake and drop the bike (or we would have hit the curb at an angle and the bike might have flipped and landed on us. I chose the lesser of the two evils.) We weren't going very fast, so neither I nor my rider was hurt; but it did cause a decent amount of damage to the bike.
After fixing it up, I was enticed by the new model year styles (and itching for a bit more power.) I purchased a brand new 600cc Suzuki Katana in 1993. I have been riding it ever since, with the only incident being some idiot tipping it over for fun. It has been completely fixed and I try to get out and ride as much as possible. I still have yet to find a bike that I like the style and colors better than my bike, although for a while, I had been thinking of upgrading to a Honda CBR900RR. I really wanted one, but wasn't able to ride all that often because of my travel job and the short riding season in Michigan.
After I moved to Colorado in 2003, I was able to ride more. I kept on dreaming of the CBR. In 2005, I went out and got a used 2001 CBR929. Wow, what a difference between the two bikes. Night and day. I still have both my Katana, and the CBR; and they both are good for different reasons. The Katana has a more upright and comfortable riding position. Passengers prefer the Katana. The CBR is essentially a land based rocket with two wheels. The power is amazing.
I have taken many trips on my motorcycles. Most of them were within a day's ride; like going camping in the northern part of Michigan, or going to Cedar Point. Kind of ironic, isn't it? Ride something that can go from 0-60 in 3 seconds that has no safety features or exterior protection, to go to an amusement park where safety is pretty much guaranteed. All this for excitement.
The only real extended trips I have taken on my bike have been a circle tour of Canada and then a tour of the East Coast. The Canada trip was a lot of fun. My brother and I went up through Canada, saw Niagara Falls, and ended up in the North Channel. Here we rented a sailboat and did some sailing and diving. It also coincided with a meteor shower, so we were able to get way out into the country for a clear view of the sky. That was still the best meteor shower I've ever seen.
We then completed the circle by going through the upper peninsula and back down the state. I remember we got caught in a horrible thunderstorm around 3 hours from home. My brother opted to continue riding through the dense traffic and rain, and I stopped to visit a friend and wait the storm out. The other trip around the east coast was very beautiful and scenic. I saw many beautiful places in Newfoundland, Massachusetts and the like. The only minor problem was an underestimation of travel time because of speed limits. We ended up riding for 10-12 hours per day. I would imagine that 10-12 hours would even be harsh on a cruiser style bike; on a cafe racer, I know it was harsh. Chalk it up as a learning experience.
Here is a picture of me and my Katana:

Here is a picture of my Katana and my CBR929:
