First trip to Spain... could this work

It is workable, Ideal would be flying into Madrid (or Malaga if possible and economic) then do Malaga, Seville, Madrid, San Sebastian, Barcelona. You could fly out of Barcelona, or get the train back to Madrid.

Just be aware, there are no good fast train connections to San Sebastian, from/to Madrid or Barcelona, expect 5-6 hours of travel, probably at least partly on Bus, and probably no direct connections.

Dropping one stop does free things up, but spending 4 nights per stop does provide a nice amount of time in each place.

I think the major issue I see here is trying to incorporate various geographically separate and culturally distinct areas in a first time trip to Spain, going from Castilla, to Andalucia, to Catalonia, and to Basque Country all in one go, you end up losing much time and energy zigzagging across the country. As a translation, imagine if a firsttimer's trip to Italy included Rome, Sicily, Cinque Terre, and Venice.

Because end of September/beginning of October is still going to be quite hot in Andalucía perhaps just focus on the central/northern half of Spain? That way you cut down your geographic spread by half and an incorporate important places you have overlooked. So maybe:

Fly in
Madrid - 4 nights
Bilbao - 4 nights
San Sebastian - 4 nights
Zaragoza - 3 nights
Barcelona - 4 nights
Fly out

If you have any additional nights add them to Barcelona.

Alternatively... if you focus central and southern Spain you could do
Madrid - 4 nights
Sevilla - 4 nights
Cordoba - 3 nights
Granada - 4 nights
Malaga - 4 nights

If you have any additional nights add them to Sevilla.

San Sebastián is great but I think 4 nights is too many, I would cut it to 3 nights. Note that I’m someone that usually stays in towns longer than most. I would visit the White Villages from Seville, drop Malaga and add those nights to Barcelona, Madrid or Seville or maybe visit Granada or Toledo.

Hi Donna, I won’t comment on number of days per location, but I will share my trip report because it covers some of the activities that you mentioned, such as cooking classes & biking in Sevilla. I agree with Carlos that your initial choices are very spread out between locations. If you’re going to Malaga for white villages ( which are beautiful), you could do a day trip from Sevilla to Arcos de Frontera, instead.

https://community.ricksteves.com/travel-forum/trip-reports/1st-time-to-spain-trip-report

excellent ideas ... thank you so much....I will share with my travel mates!!!

Drop Malaga.

Four days in Donostia-San Sebastian may be too much, I´d split them between Bilbao an D-SS. Take into account northern Spain has a very unreliable weather and rain is often an option, while beach weather is rare...

MikelBasqueGuide - can I ask why I should split time between the two when they are only 1 hour apart? I'm serious about this question. 2 hours by train.

San Sebastian is a very touristy place. It's very attractive, but for me the environment got old quickly. I preferred Bilbao by a considerable margin--far fewer tourists and a larger historic center. But I'm not into bar-hopping, even for tapas. I like to eat sitting down.

I would:
Fly into Bilbo BIO 4 nights
Bus to Donostia 4
Train to Zaragoza 3
Train to Sitges (via Barcelona) 3
Train to Barcelona 5
Fly out BCN

We did this in 2018

Thanks for all the comments. We had good conversation with our travel mates. We meet them face to face next week for a trip to the Virgin Islands and will talk more. I'll keep checking and if we come up with a plan I will post again. Thanks. Happy Thanksgiving to my US posters!

To expand a bit on the comments about dropping Malaga: It's a nice city, but it takes longer to visit the white villages from Malaga than from Seville, according to ViaMichelin.com. I plugged in Ronda, Grazalema and Arcos as destinations and found a round-trip time from Seville of just over 5 hours, compared to well over 6 hours from Malaga. I'm not suggesting that you go to those three places in a single day, even from Seville, though I think Arcos and Grazalema would be possible via car in a single day. The problem with hitting that area from Malaga (based on a look at the ViaMichelin.com map) is that the trip between Malaga and Ronda involves a lot of extra miles rather than a straight shot westward.

I agree with Carlos to focus on one area of Spain so that you aren't wasting time traveling all over the country. And if you choose central/southern Spain, I think Carlos has suggested an awesome itinerary. He includes all the places that are very important historically and culturally, and that are also beautiful as well.

And I would definitely include Malaga. Malaga is a lovely city on the Mediterranean that will give you some coastal ambiance, and I think this adds a nice diversity to your otherwise inland trip. You can take an awesome hike to the top of the Alcazaba, and enjoy exotic flowers, lush greenery and stunning views along the way. Stroll along the seaside promenade and enjoy drinks while watching the sunset. Visit the Atarazanas Market where you can browse, shop, and eat. The historic city center is beautiful with all kinds of shops, restaurants, and cafes.

Since you are starting your trip late September/early October, most of your trip will be in October. This should be a good time to visit Andalusia weather-wise.

Please don't rely only on Rick's guidebooks. He omits a lot from his books. I recommend Lonely Planet, Michelin Green Guide, and The Rough Guides.

Thanks again your ideas. I think we will drop southern Spain as recommended by Carlos since we probably will traveling more in September than October- gives us a reason to return to Spain. I’ll keep you posted once we talk with our travel mates next week. I’d like to book our flights before the end of the year as I have travel credits I need to use up. Thanks for all the comments - back soon