A possible 60-day itinerary for Spain and Portugal

I would add Valencia. Can't imagine a month or more in Spain and not visiting this fascinating city.

I recommend Comillas over touristy Santillana del Mar. We regretted staying in Santillana and loved our time in Comillas.
Also, Madrid , consider a day trip to Segovia.

I haven't dug into the train and bus schedules, but I think you'd do better to spend 2 nights (or more) in Malaga rather than treating it as a day-trip from Granada and then making the fairly long trip from Granada to Ronda later. Ronda's quite a bit closer to Malaga than to Granada. For that matter, so are Nerja and Frigiliana. All your Granada day trips would probably be better as Malaga day trips. I'd want 3 nights in Granada without any day trips; having just 2 nights there would be rushed.

I think you could shift one of your Ronda nights to Granada/Malaga.

Two nights in Santiago de Compostela may be adequate for that town, but there are a lot of other worthwhile places in Galicia. I'm sorry you won't have time for them.

Bilbao's almost twice the size of San Sebastian and much less touristy; I'd rather have 4 nights there than in SS, though it definitely depends on what side trips you're planning.

You won't have much time in Madrid after you take your two day-trips, but I'm guessing this isn't your first trip to that city.

I'd happily whack away at the Algarve time, but I'm not a beach person.

I would take a night from Ronda and add it to Seville so you will have 5 nights in Seville. So much history in Seville, wonderful sites, and gorgeous city for exploring.

And, if possible, I would spend 2 nights in Malaga instead of visiting as a daytrip. I think you have too many daytrips planned from Granada. Daytrips can be tiring.

Our experience- currently in Spain for 89 days, about 1/2 through our trip. Based on our experience, you have too much time devoted to Ronda, for sure, and even Cordoba. I would suggest moving 2 of the Ronda nights to Seville.

Overall, I’m wondering if you’re giving enough time to Madrid and Seville.

And to think out of the box - what if you did all your time in Spain and saved Portugal for its own 30 or 60 day trip? 😉

Suggest some minor changes.
1) Evora, 3 nights, cut to 2, you don't need three nights there.
2) Lagoa 5 nights, cut to 3, add two days to visit the amazing Douro River Valley from Porto. Take the train up to Pinhao or Regua.
3) Segovia 2 nights, do on a day trip from Madrid instead.

I strongly agree with the persons who said to make Segovia a day trip from Madrid. We did this and it worked out perfectly. If you really wanted to be there at night, you could do an overnight trip from Madrid. More than 1 night in Segovia is not needed. Not enough to see and do, even if you’re just relaxing.

Thank you all for your suggestions. I've made note of them all, and I will definitely do some rethinking based on your input.

This forum works best when it works like this. I really appreciate every one of your comments.

Oh my goodness…if you could be in Valencia for Las Fallas (Mar 15-19) that would be amazing! If big city festivals aren’t your thing, a lot of the smaller towns around Valencia all have their own Fallas celebrations.