I’ve spent most of my adult life working remote (also in tech) and have had some trips like this that were fantastic and others that were big hassles. The determining factor is whether the location you go to is conducive for actually working, otherwise you spend way too much of your time trying to sort out stupid logistical things (where can I hold a call? How flaky is the internet? How do I sync hotel checkout to work schedule? Etc). But some locations are designed for remote workers.

Look on the map specifically for coworking and read reviews and look at pics to get an idea. Consider getting a Spaces membership, which is a very large network of coworking through most of Western Europe and some other countries , where you can drop right in and everything “just works”.

I have a wife and kids now so it’s not as easy for me to float around as much, but I’ve had some excellent week long trips or even just long weekends through much of Western Europe. There are many places with budget flights and you wouldn’t necessarily go to on serious longer holiday, but are awesome destinations for this kind of travel. You get a chance to have a taste of those places and don’t use up your PTO.

A recent place I went like was to Taghazout, a cool beach town with a bunch of surfer tech nomads and lots of coworking spaces. I went in April on a $50 Ryan air flight (in/out Agadir). It was a great trip.