Extremadura

If traveling by train and using busses for day trips look at Plasencia, Cáceres, Trujillo, Guadalupe, Mérida, and Zafra. Those are the larger cities in Extremadura. There are plenty of smaller towns one could visit, but without a rental car getting to them could be an issue.

I always have a rental car, but I believe all of the cities I mentioned, except Trujillo and Guadalupe, are on the main train line.

I loved the Extremadura region, and especially Cáceres. The town has a unique charm and I could have stayed much longer. Here is a snippet from Lonely Planet because I don't have the right words to describe it, but so true:

Cáceres has narrow cobbled streets that twist and climb among ancient stone walls lined with palaces, mansions, arches and churches, while the skyline is decorated with turrets, spires, gargoyles and enormous storks' nests. Protected by defensive walls, it has survived almost intact from its 16th-century period of splendour. At dusk or after dark, when the crowds have gone, you'll feel like you've stepped back into the Middle Ages.

And it is correct - you really do feel like you have stepped back in time. I would highly recommend a visit here and to the region. Sorry, I have no idea about public transportation, though, as we had a car at the time.

I stayed in Caceres and Plasencia (the latter in transit), visiting Trujillo (by bus) and Merida (by train) on day trips. For me in 2016 the transportation was reliable if not necessarily frequent.

Extremadura is a very worthwhile, under-toursited area. To me, Caceres was the most interesting town. Merida is a target primarily for folks interested in the Roman ruins and the nice, modern archaeological museum; the city itself isn't particularly charming.

I haven't carefully researched October weather in the area; you should do so. For that area, you're threading the needle between excessively hot summers and rather cold winters. It was getting quite hot in early June the year I was there. With luck you won't encounter the 90F temperatures Caceres had earlier this month; maybe the second half of October would be better a better bet.

My usual source for daily temperatures (timeanddate.com) has only spotty data for Caceres over much of the last ten years. Data availability is a lot stronger for Merida. Here's a link showing actual, day-by-day, historical weather data for October 2022; use the pull down box at the right, just above the graph, to display statistics for a different time period.

Merida weather -- October 2022

At a quick glance it appears the weather pattern shifts from summer to fall in October. Unfortunately, that doesn't exactly happen on the same day every year.

You are going to LOVE Extremadura, not only Cáceres (UNESCO World Heritage) but also Mérida, Trujillo, Plasencia, the monastery of Guadalupe, Hervás and its Jewish quarter, Zafra in the province of Badajoz, Olivenza, the Jerte valley and its amazing gorges, Monfragüe natural park, all the small towns you´re going to find in your way...Very affordable, excellent food (ibérico ham!!) and amazing places.

Thank you everyone! I am really excited to explore the possibility of a trip to this part of Spain!

It´s nice to see questions about other parts of Spain!!!

As for the wine, make sure you know whether the Extremadura you had in Portugal was actually from Spanish, or Portuguese, Extremadura. (In the latter case, the label would have read Estremadura.) But regardless, I believe that Extremadura, Spain is a great place to visit. As my two visits, so far, are receding into the past (2003 and 2014), I don't have up-to-the-minute information, but I will say that loved each of the cities and towns I visited -- Caceres, Trujillo, Merida, and Zafra. Also, I made these trips easily by train or bus. In addition to the region's inherent interest and charm, I appreciated the relatively lower levels of tourism; and though perhaps I wasn't bound to encounter much tourism in November anyway (the month in which I made each trip), everything I hear, and read, indicates that tourism here is generally well below what one encounters on Spain's beaches and in its famous "must-see" destinations (most of which, after five visits, I haven't seen yet).