I've had a 300cc Vespa GTS for a decade now (alongside a few motorcycles) and the thing that is the most striking about it is how relaxing it is to drive. Despite being somewhat heavy, they are very manoeuvrable due to the low center of gravity. The suspension is very good and despite the roads here being awful it just glides over any bumps and smooths them out. The 300cc engine is fairly quiet and provides more torque than you need. When the lights turn green you'll be over the intersection before the motorcyclists have had time to release the clutch and get going.
It does well on the open road too. It isn't a race machine, but it'll do 120km/h (75 mph) which is good enough. And you won't feel stiff and bent when you arrive if you decide to take it on a 6 hour ride.
I didn't get it for the looks/style. Yes, I did think it was a bit of a gimmick. And then I tried it. I thought I was doing 60/kmh when I was doing 80km/h. And it just glided over bumps.
(And yes, I have a motorcycle as well, but I'm European so it means I don't ride a motorcycle to get into road rage incidents. We actually try to get along here)