Andalucia in late October 2023

Regarding wines in Spain,

Andalucía is really only known for Sherry, around Jerez de la Frontera one can find many Sherry producers that offer tours + tasting.

The Madrid region is not the best place for winery tour/wine tasting, La Mancha (DO) is more quantity and less quality kind of stuff.

North of Madrid is the Calatayud (DO) wine region and westwards is Rioja (DOC) wine region, which are of higher quality, but may require a few extra days to side trip to.

Wow! I applaud your itinerary and pace for the schedule allows for plenty of "be there" moments.
Thought: while journeying to vineyards for tours and tastings make a great experience, I have shifted to seeking excellent wine bars. Point is the niche wine bar experience has grown and essentially provides the opportunity to sample a wider array of wine and food pairings with less investment of time. PM me if you desire some recommendations for Madrid.

My husband and I spent six weeks (mid-Sept through October) in Spain this year. Late October weather was perfect in Andalucia, which is where we did the latter part of the trip. I am in the minority in that Seville was our least favorite part of our trip and Madrid was one of our favorites (we like museums and the energy of a big city). We loved Granada, and I would add a day there (taking a day from either Seville or Cordoba). Toledo is beautiful and definitely worth some time. We had planned to see Segovia, but never made it as we got on the wrong train and then everything that could go wrong that day did. Regarding flamenco, we went to a show in Seville at La Casa del Flamenco and highly recommend it.

La Rioja is the wine region of Spain that’s a 4h drive north of Madrid and I believe you need a car to explore it. You could take two nights away from Sevilla and one night from Cordoba and Madrid. If you take a night away from Madrid that means you won’t be able to see Toledo that I highly recommend.

Local tour guide recommendation for Granada. Margarita. [email protected]

I love your itinerary and the allotted number of nights. If I were to tweak it, I would recommend dropping one night from Cordoba and either adding it to Madrid so your day trip to Toledo doesn't take away time from Madrid. Or keep Madrid at 4 nights and spend one night in Toledo, which I think is much more enjoyable than visiting Toledo as a daytrip.

I would definitely spend 4 nights in Seville and 2 nights in Granada. This is based on our first-hand experience visiting these cities.

We were just in Spain this past October 1-24. The weather was great, very warm but not hot. We had two mornings (Madrid & Toledo) with very light rain and it lasted less then an hour. I would not take a day from Madrid and add it to Granada, we stayed 3 nights and felt it was one day too long, but we don’t like 1 or 2 night stays. The Alhambra and Cathedral are the two sights worth visiting. The city is lovely to walk around. It is flat till you start up to the Albaicin & Sacromonte neighborhoods. Then it is extremely hilly with uneven streets.
We loved Seville and were so busy we wished we had another day to just wander around more. We stayed 4 nights also. We did a city walking tour, cathedral & Alcazar tour, a cooking class, a flamenco dance class, a flamenco show, a boat ride down the Guadalquivir river. The only museum we made it to was the Bullfight Museum by the water.
You could drop a night from Cordoba and add to Madrid. The Cathedral there is a don’t miss, nothing we’ve ever seen before. Otherwise the city is beautiful and clean but not much else going on. You can tour the Patios yourself. no tour needed.
We had a good time in Toledo too but again, one day would be fine. It is very, very hilly. Their cathedral is also magnificent.
We spent 6 nights in Madrid and a bullfight and soccer game were the highlights for us. The Prado is huge and since we don’t know too much about art, we booked a private tour - 3 hours was perfect.
You have to read about what would interest you. My husband was in the Navy and Merchant Marines so we always go to any military or maritime museums around. Later in life he became a chef so we always hit the local markets. I love an ethnographic museum to learn about the culture of the people. Read what you would like to see and do and plan the number of days based on activities. That’s how I plan all our trips.

Looks like your planning is off to a good start. A few notes:

-I’d swap for two nights in Cordoba and three in Granada. Granada has more to see, across a larger area to wonder—don’t miss the Basilica of San Juan de Dios!
-Four nights in Madrid is a minimum to do the city itself any justice. It doesn’t really leave time for side trips. (Some on these forums think the city isn’t worth more than the three major museums. They’re missing out.)
-I was very pleased with the “city into” tour with https://sevillawalkingtours.com/. I actually wish I’d done the cathedral and alcazar with them.
-Not a tour, but https://www.madriddarracott.com/en/ is a great shop that does daily wine tastings. (And less regular tastings of Sherry, Vermouth, and others.

I liked Cordoba and was glad I had two nights there, but three wouldn't be needed unless you plan a day trip elsewhere. Granada may need more than two nights since the Alhambra takes the best part of a day. If you have an extra night/day to play with, I'd say Madrid, which is full of things to see and do.

Based on my limited experience, late October weather should be good, though it might be cold in Madrid because of its altitude.

Madrid was not cold this past October.

Thank you all for your wonderful comments and suggestions! I so appreciate the time you took to provide detailed information and suggestions. Your comments made me feel better about our planning. I will certainly look up the references you shared. Happy Holidays to all!