There are two main layers, so to speak, to how I choose where to go. The first is practical:
1a. Which country:
- in or out of the Schengen area?
- a country I feel at home in, or have I an urge to go somewhere new or to expand my boundaries and push myself a bit?
- time of year and climate
- need or not for visa
- distance from Italy
- how I would get there (I greatly prefer ground travel, i.e. bus or train)
- miscellaneous other factors, not least my emotional state at the time
1b. Are there mountains?
If yes, is there infrastructure (good or at least decent WiFi, plumbing, grocery stores with fresh veges & fruit and basic toiletries; modern building standards) and could I get a decent apartment for a reasonable price for a month or so in a mountainous area + are there walking tracks in the mountains? (e.g. around Sarajevo you put your life at risk if you stray from roads or well-trampled paths because most of the hills around the city still haven’t been swept for mines since the city was beseiged in the late 90s).
Experience has made it crystalline clear that to function optimally on a daily basis, I need to be up in the mountains in fresh air and negligible noise pollution, where I can pop out my door and go for a walk among the hills that restores and nourishes soul, mind and body.
1c. Summertime (mid-June to mid-Sept) has its own set of considerations: can I get a place meeting the above criteria in a cool-enough climate for a price that’s not grossly inflated (3x – 10x above off-season rates)?
For this reason I book my summer accommodation (and tickets, if I have to fly) preferably by the end of February. I’ve learnt the trick of looking for ski resorts, which tend to have good infrastructure and lots of accommodation options and be (somewhat) cheaper in the off season.
2. Choose an area or two and plug my criteria into the Booking app and see what’s available. Pull up map view to get a sense of where they are. Rinse and repeat until I find something that satisfies me.
In the beginning I always used Airbnb, but these days I almost exclusively use Booking because I have so much on my plate professionally right now I don’t have the mental or emotional bandwidth to deal with hosts’ emotions and expectations (and defensiveness); I just want to deal with professionals.
Nevertheless, even on Booking I do end up renting apartments listed by individuals, but what I’ve learnt both from experience and from talking to hosts, is that when guests reserve a space through Booking, the host knows that the guest has high standards and expects to deal in a professional manner, whereas Airbnb is so much about “experience a place like a native” and “connect with locals”. As far as I can recall, any negative experiences I’ve had have been with places booked through Airbnb.
That said, if I were a tourist, I’d happily book places through Airbnb for exactly those reasons of getting the local perspective and connection. But I don’t have time for that, these days! I just want to be left alone to live my life in a place where I can establish routine as quickly as possible after arriving.
For that reason, since the first year (2016), I’ve spent most time in places where I’ve stayed before so I can drop right into routine: I know where to buy the things I want to eat, I know where to buy the toiletries and sanitary items (!) I need, I have my favourite caffe-bar(s) for my morning coffee, I know where the walking and trail running routes are, I know enough words in the language to perform everyday transactions, etc.