Re: SS It may not be great weather in this special place..Ocean breezes can become Atlantic winds so easily and the dampness can be a killer. That said SS is super. I wouldn't advise driving from Madrid, as for weather cautions but the train would certainly reduce the stress as it is a long way. English is spoken in many places as is Spanish (Castilian) so the language was no problem while we were there last Oct..Why are you leaving Madrid if you only have 4 days???..Plenty to do there and day trips are available.Have a great time whatever you decide.

It is so simple to get to Sevilla and Cordoba by train, and the chance of nice weather is so much higher there, it certainly seems the safer bet if you feel you must book ahead.

Toledo near Madrid is very nice to visit on a nice day or weekend.

sunny Valencia is only 1:38 hour from Madrid.
I would not go north in Jan.
p.s. Madrid can be cold in the winter

You'll have no problem in the Basque country with your Spanish. The Tamborrada takes place on the 20th of January in San Sebastian. It's one of the great 24-hour festivals. Don't miss it.

www.donostiasansebastian.com/tamborrada/
www.basquecountry-tourism.com/culture-festivals-san-sebastian-tamborrada.php

It the weather is decent, I'd drive, stopping overnight in Pamplona or a little further south in the Rioja. Pamplona's only an hour's drive from San Sebastian and there is generally something going on, food wise.

Bilbao (not Bilboa) is also interesting, even during the dead of winter, and again, the food is great regardless of the time of year.

If there is a huge festival going on in San Sebastian during the time you are considering going there, and if you are going there to eat at some of the legendary restaurants, then I would call those restaurants and make sure you have reservations.

Likewise for hotel reservations. It doesn't look like you just wing it if you are planning on going around the 20th, which would be my preference, because I like to see a weather report.

Is food the main reason you are going to Spain? Because it is the main reason most people go to San Sebastian in winter.

You can also find good food in Madrid and other parts of Spain. The food in the Basque area is exceptional, but there is delicious food in the other destinations you asked about. You can look at recent reports on Chowhound about Sevilla for recommendations for tapas, restaurants and food shopping.

If your Spanish is as good as your spelling of Spanish cities names I would suggest you stick to English while in Spain....(Not Bilboa-- Bilbao; Not San Sebastion-- San Sebastian; Not Granda-- Granada)

>>Since it is winter time, will all of the restaurants be open in the northern area?<< I am pretty sure there will be 1-2 restaurants open somewhere in Northern Spain, but maybe not all

thanks for all of your replies, particularly the websites about the festival in SS. We are already planning to do a day trip to Toledo from Madrid, and also expect cold weather there! I am leaning more towards heading south, and saving the Basque area for a future trip. And so sorry, Viajero2, but I am not a great speller, and don't know why you are so snarky.

Often it is not the spelling but the slipping fingers..Even with a masters in Education I have been known to misspell things.
Viajero...chill out. You did sound snarky.

If I was in Spain in late January (which sometimes happens), I would not miss the Tamborrada for any reason. There is nothing to compare, and you can join in the celebration!

How long in total is your trip?
As for the north versus south it would help,to understand your interest and travel style before advising.

I agree with Robert that anytime you get a chance to go somewhere in spain during their big festival it makes for a great, unforgettable experience.. However, as much as I love Northern Spain it is a cold, rainy place.

The weather in the Basque country isn't much different then it is in the Pacific Northwest (Vancouver, B.C. to Seattle), where the weather is generally pretty decent year around. And no, it doesn't rain everyday...