I have yet to go on a truly long trip. The longest so far was 2 hours each way. Whether in a group or solo, it has a lot of appeal. It’s that whole independence thing. So here’s an excellent website about one woman’s trip cross-country on her Vespa. Awesome! http://vespa-vagabond.blogspot.com/
Very inspiring. Here’s a photo from my trip to Yellow Springs Ohio. We stopped at the famous Young’s Dairy on our way back.
You can see my scooter’s first name is still visible. (Yay!) I tried my best to pack everything so that it was not beyond the center of the back wheel. It is hard to see what I packed, because I have the rain covers on them. However, we lucked out and didn’t hit any rain.
Here are some other scooter-trip diary websites:
(These links were originally gathered by Crystal of girlbike.com fame on a scooter diva thread posting.)
And someone on a ModernVespa thread recommended maps from these people http://adventurecycling.com/routes/index.cfm because they avoid highways. Created by bikers (as in bicyclists) but suitable for scooterists.
There is much more information online, and remember that people take similar trips with large motorcycles and also bicycles, so those types of forums/sites will also have good tips.