Guess where?

[Muizer]

How does one figure that out?

Because of the hints "colonial" and "not quite Spanish". Until then I actually thought those 2 mansions/palaces were some sort of fake/replica. In the end I searched for 'Portuguese colonial architecture' and there were some hits for the nearest of the 2. Took some extra time because the first referred to Guinea Bissau :/ It really is mostly obsession driven 'grunt work'. Once I start looking I can't stop :p

[lolIsuck]

Horta it is, well done Muizer.

How does one figure that out?

I mean, there are quite a few clues in that picture.

• It's a coastal town and the elevation goes up immediately which could mean volcanic island (not necessarily but it's an option).
• The town itself doesn't look that big yet it has two historic looking churches, a "mismatch" often found in main towns on islands.
• The churches are to me quite distinctly Iberian colonial.
• As Muizer noticed the town itself doesn't actually look that old and lacks many distinctive features a historic town in Europe would have which makes the continent itself less likely
• The entirity looks well-maintained, in most former colonies at least some things generally look a bit more worn down or less developed making them less likely.
• The vegetation is a mix of temperate and some Mediterranean/subtropical vegetation which fits an island group in the middle of the Gulf Stream.

It's also the legislative capital of the Azores, I didn't just pick some random town. It's not exactly a 1+1=2 but not everything should be in this game IMO.

[Septentrionalis]

Jebus. No one has complimented me quite as you just indirectly did. You must have a very high opinion of me, if you hold me to those kinds of intellectual expectations.

I sincerely appreciate the lengthy explanation and now, having read it, I feel I will be better at this.

[Muizer]