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I really enjoyed San Sebastian. Not that many things to see per se, but the overall vibe, the seafront and the food is amazing. Don't know, if it really qualifies as underrated, though, since the whole city seems to be involved in tourism.
Bozen. Amongst my favourite cities in the Alps. Love to stroll through those narrow alleyways. Always has been a stop when we went further south. Great memories.
Helsinki. Don't know why people go crazy about the other Nordic capitals, but don't bother about Helsinki. Spent quite a few weeks up there, awesome.
Tallinn. The centre is stunningly beautiful. Definitely surprised me.
Leipzig, Germany is a nice little 'biggish' city. It has a cool alternative vibe and it's not too hard on the wallet, either. I'm surprised it doesn't seem to get lumped in to Berlin day trips more often since it's only about 170 km down the autobahn. It's a city that would probably please the same kind of crowd that's attracted to the capital. In Germany, 170km mine as well be 100km.
Hamburg. Germany's second city but it seems that it's just the fifth-most popular city tourist destination after Berlin, Munich, Cologne and Dresden. However, it's so much better and way more vibrant and interesting than sterile Munich(IMO).
Interesting. I was excited to see Hamburg and felt a little disappointed by it, while I thought Munich was cool when I expected to not like it at all.
I know Munich has a reputation for being a city for Germany's rich, too, but all I ever heard about Hamburg was how pricey and built up it was. I ended up feeling like it just sort of came off like any other Northern German big city, but without very obvious evidence of all this posh activity and economics. I saw a few expensive cars, and the some of the canal areas are really nice, but it wasn't what I was expecting based off what I heard. I had no one to meet there to show me it in a personal way, so as an ordinairy tourist I felt like it wasn't as grabbing as Munich was. It's probably a great city if you can afford to live there, but I think almost in general, the North of Germany isn't the best place for 3-4 day sightsee-ers. I know that makes me sound hypocritical because I just mentioned Leipzig, but at least there you can have your fun for cheap on top of indoorsy things.
The first place that sprang to mind when I saw this topic was Ghent, Belgium. Overshadowed by Brugge just down the road, that everyone raves over.
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