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We have been living and sailing around on our boat for many years, but decided that perhaps the time had come to move ashore, this was thinking about the onset of old age (not there yet, but to set up a viable and sustainable land base we know will take a few years). So, we first asked ourselves what we needed to survive. Good land, sunshine, water, security. As Europeans we still have (but for how long?) a free health system. Having sailed through the Azores before we decided to stay a while on our next trip through. We put our boat to bed for the winter and rented a very small cottage (more like a stone shack!) and hunkered down for the winter. First I dug over all the garden and planted as many things as I could, learning so much along the way. We searched for land at a price we could afford on the island that we were staying, but alas the cost of prohibitive, also, there is only one doctor, and when he can’t help, he sends you by plane to another island…. what a hassle. So that made us decide to move to another island. We managed to buy a fantastic plot of land, which wasn’t too far off what we really wanted, amazingly it is possible to build (legally) as there is an old ruin that is stated on the deeds to the property. The winter here is wet, with amazing atlantic storms, the main problem that I have encountered is standing water in my garden, I have now decided that we will have raised beds. As our background is living on a boat, self sufficiency is second nature to us, you have to know about food, storage, water, power when thousands of miles out at sea… or die! We would like to go fully self sufficient with power in the future, but will for the time being use the grid as we will not have to put in the initial investment. Things like lithium batteries are coming down in price all the time. There are no real problems living here, just remember it is Portugal, and like Spain, they work on a different time scale to the rest of Europe (slow). Most people do speak some english, which is both a help and hindrance as it makes language learning difficult.
If you are thinking about the azores, spend time on the internet looking. But if possible, come in the winter, so as you get a feel for the real place, it then gives you a chance to look around and ask people what land is for sale etc. Buying land/property in portugal is now a lot easier than the past, once you have found something, get a lawyer and he does the rest… allow about 300 euros for his fees (he will also act as the notario).
We are living by our selves, not in a community, though we are always happy to help out when others need it, and to share what we don’t need, I don’t know if there are any dedicated communities here, but there are a lot of like minded people.
Good luck with your search… and to give you an idea, we bought our land for the price of a small second hand family car!