What three winters in a row taught us about the Algarve
We have now been to the same stretch of coast in January three years running, and the thing I would tell anyone starting out is that a summer visit tells you almost nothing.
In August the town we like has four bakeries open, a market on Saturday and someone selling fruit from a van. In January there is one bakery, the market is half the size, and the van is parked outside a house with the tyres flat. It is simply a different town, and it is the town we would be living in for a good part of the year.
The second winter we started paying attention to small practical things. Which restaurants actually stay open. Whether the bus to the bigger town still runs on Sundays. How long it takes to get a plumber in a month when half the trades are working inland. Whether the flat gets any direct sun at all between eleven and two, because a south-facing window in August and a south-facing window in January behave very differently once the sun sits low.
I keep the search on https://global-property.investments/ and I have a note on every place we have seen about what it was like on a grey Tuesday, which is not information anyone puts in a listing.
The third winter was the one that convinced us. We rented in the exact building we had been circling, for two weeks, in the worst weather of the year, and came away happier about it than after any summer viewing.
My advice, for what it is worth: go once when it is beautiful, and once when it is not.