I haven't actually booked anywhere yet as I'm largely going to wing it. It's likely that my first stop will be Las Palmas (https://nomadlist.com/las-palmas-gran-canaria-spain/scores). It's not too culturally different to where I live now, so it should be a more gentle introduction to the nomadic lifestyle, but the cost of living is also relatively cheap.
No shit, I'm doing the exact same thing at almost the exact same time. I've got a few months savings in the bank, and I'm heading off to Las Palmas... stopping along the way in Europe. See you there!