Well I wasn't alone, but did it 18 years ago. You will need to book a lot of hostels in advance as by the time you hit June, hostels in places like Rome, Paris, Berlin will be full.
So if you can pick a route and maybe allow a day or to in-between to check out some smaller towns.
Rail pass is great, trains seemingly go anywhere at any time. Most cities have really good public transit, and a lot of areas are small enough that you can walk around. I know we timed out a few night trains for some longer trips, but the day after those, is a good laundry day where you take it easy, and get a bit more sleep that night.
I thought Paris had a lot to see, as did Rome and Venice. Vienna, at the time was a nice clean city, that I thought had some striking women. Munich was also a fun place to spend a few days. Enjoyed some quieter time in Switzerland as you can go to a place like Interlaken, take an hour long train to a mountain town, than hike up to a couple other's. Different than here where it's so vast in the mountains.
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