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Porto, Portugal
Porto is a coastal city in Portugal that still has a medieval vibe with its baroque, gilded churches and narrow cobbled streets that spider past merchants houses and cozy cafes. The average temperature here is 66 degrees in September, so it will still be warm, and you won't have the annoying lines to all the famous spots since the tourists have thinned out.

For example, you'll be able to pop in and walk around the famous Lello Bookstore without bumping into fannypacks, and get to wander the Bolhão’s market like a local. 
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