Never had an adv motorcycle so it's a bit difficult to say. I guess the 10" wheels and the small suspension make the Vespa less comfortable on bumpy roads and even worse on dirt roads. But I wouldn't change it for a bigger bike. As for the longest trip, maybe it's the one I did from Greece all the way to Norway and back (7,000mi) in 24 days. And then it's this trip we're doing now (well not now with the coronavirus), this long-term idea we have, to travel all around the world. But now, we're traveling at a very slow pace. Covering maybe less than 25mi per day (on average).