Improve/Shoot holes in this itinerary please!

That's a lot of moving around. 2N in a location gives you one full day and maybe a couple hours on either end when flying, maybe a half day or so using the train.

If you mean next month, don't plan to visit Granada unless you have a ticket for the Alhambra. Tickets sell out every day. I just checked the official website and tickets are already sold out through Oct. 19.

The whole Tangier thing sounds impractical. Looks like 3-4 hours to get from Ronda to Gibraltar for a day trip (where's your luggage?) and then to Tarifa (don't know if there's much of anything to see/do there - I skipped it). Ferry to Tangier for a day trip (where's your luggage?) and get to the airport with enough lead time. Add to that, Gibraltar is not all that much and Tangier is the one of the least interesting places in Morocco. Before I chose my 2-week tour of the country, I looked at any number of 10-14 day itineraries - not a single one included Tangier.

The Ronda > Gib > Tangier part is the most uncertain for me

For me too, especially because the Straits of Gibraltar have gale force winds in the Autumn season, they will often cancel the ferry if it's too windy, that's a big risk considering that's what your second half of your itinerary is predicated on.

Also you seem to be skipping a lot of very interesting places in Spain in order to cram in a slice of Morocco and Portugal at the end. I'd say save those countries for when you can do them justice, and focus on Spain. Many foreigners find surprising that there are not too many land connections between Spain and Portugal.

Consider you are missing out on Zaragoza, Bilbao, Madrid, overnight in Cordoba (very important), extra nights in Sevilla (3 nights is short imo)... all of those are easily added to the basic itinerary, they will also make it so you don't have to fly. You could do

Barcelona
Zaragoza
San Sebastián
Bilbao
Madrid
Granada
Cordoba
Sevilla

I liked Bilbao more than very touristy San Sebastian, but even so, I wouldn't fly to SS for just two nights. If it were a 2-hour train ride from Barcelona, that would be different. Are you really going to be happy heading back out to the airport (getting there 2 hours before departure time) just 4 days after you've arrived from the US?

I agree with the others. You're allowing too little time in the key destinstions in order to go to highly marginal places like Gibraltar, Tarifa and Tangier.

I believe there are flights from Seville to Lisbon if seeing a bit of Portugal is a must on this trip. (Or if the trip is this year and you already have a ticket from Lisbon back home.)

Land in Spain and let the train take the strain. You'll be glad you did.

I agree with everyone who says this is a lot of moving around. You are shortchanging really important destinations (historically and culturally important) for secondary sites.

I would drop Gibraltar, Tarifa and Tangier and perhaps Ronda. I would do something like this:

Barcelona - 4 or 5 nights (there are a lot of interesting sites in Barcelona; additionally you need a day to get over jetlag)
San Sebastian - 3 nights (I haven't been to SS but it is a long way from Barcelona, so take a night from Tarifa and add it to SS)
Granada - 2 nights
Cordoba - 2 nights (The Mezquita is amazing but there are other interesting sites in Cordoba; the Juderia is wonderful for wandering around and exploring: narrow lanes, white-washed buildings, patios)
Seville - 4 nights (a beautiful city with so many important historical and cultural sites; 4 nights is a minimum for Seville)
Madrid - 2 nights (not enough but better than nothing; if you are interested in art, you will love Madrid which has some outstanding art museums)

With this revised itinerary you would fly into Barcelona and home from Madrid. I really think spending all of your time in Spain will give you a more enjoyable trip. I think a trip is more rewarding when you have some time to wander and explore neighborhoods in addition to visiting interesting sites. Visit Portugal and Morocco on separate trips. With your current itinerary, you will be spending too much time on planes, trains & ferries.

I'd like to thank everybody for their candid, creative, insightful recommendations! I'm still tweaking my itinerary, based in part on these suggestions, please keep them coming! Much obliged. :)

Just got back to San Francisco on Saturday night, I want to thank everyone again for all of your advice! I changed my itinerary around in part due to the advice here, and was VERY happy with the results. I'm sharing this info, as a recommendation, or aid to others, for a great 'survey' (ie, not a deep dive) trip; I'm being honest based on my feelings so I apologize if any of this offends. I do realize that with a deeper dive, there is more to appreciate everywhere! I'm also leaving out a lot of detail RE specific places I visited in each location.

• SFO to Bilbao. Bus from airport to downtown Bilbao, walked a lap around the lovely Guggenheim (TBH I was more interested in its exterior than its interior, especially given time constraints) and its environs.
  • Train Bilbao to San Sebastian, 2 nites there. Gorgeous city, beach; amazing food!
• Fly to Lisbon, 4 nites there. Side trips to Belem, Sintra. For whatever reason (too tourist oriented? traffic? too many Ubers? looked a little run down?) Lisbon was not my favorite, no offense to anyone.
• Fly to Sevilla, 3 nights there. LOVED Sevilla! Could have stayed another night.
  • Day trip to Cordoba by train seemed sufficient to me for this 'survey' trip, the Mestiza was jaw-droppingly beautiful! Nice walking around Cordoba; great food in Sevilla and Cordoba!
• Train Sevilla to Ronda, half a day in Ronda (stowed luggage in locker at nearby bus station), I think if I had spent the night there I'd be frustrated and bored so a half-day was perfect for me.
• Same day, train from Ronda to Algeciras, and bus to Gibraltar. 1 night in Gibraltar. I'm glad I was able to fit Gib in, it was a fun break to see a bit of the UK! And the history of the rock is cool. Also fun to walk thru passport check, and across airstrip, on the way into town. Lots of great views, walks, apes on the rock. :)
• Bus from Gib to Tarifa via Algeciras, 2 nites in Tarifa. Thank you, RS, for recommending Tarifa! What a cool, fun, chill town to use as a base! More great food, very laid back pretty old town.
  • Day trip via ferry to Tangier. Another culture, another language (I think I went to 5 different language areas on this trip lol), I'm glad I went! But TBH I returned earlier than I had planned, maybe it was a bit too much for me (especially with all the guys trying to be my guide -- annoying).
• Early bus Tarifa to Algeciras, then train to Granada, 2 nights there. Another city to which I could have added an extra night, such a great vibe, more great food, busy but not crazy busy. The Nasrid Palace in the Alhambra may be one of the two most beautiful man-made places I've ever seen (the other is the Sagrada Familia!). Wow.
• Flew to Barcelona, 4 nights there. Classy city, amazing public transportation, cool people! Insanely great architecture, Gaudi's buildings in particular make me smile. I had high expectations for Sagrada Familia, and it exceeded those expectations, it's so amazingly beautiful. Amazing food, great city to walk/metro/bus in.

Thanks again everyone! If anyone has any questions on logistics/details, please let me know, I will be happy to share! I can't wait til next time, when I can do a deeper dive into some of these places, and check out other places that y'all have recommended. :)

Thanks for the honest report. I’m planning a trip to northern Spain and have a quick question.
When taking the train from Bilbao to San Sebastián (Donostia) did you use Renfe and did you prebook your ticket. I’m looking on Rome2rio and it is telling me there are only buses, no trains.
I want to go in the opposite direction.

thank you for your trip report. We are looking at a similar itinerary for next October but we have a few more nights to explore. Probably won't be adding Lisbon or Ronda though.

Hi Barbara -- The train that I took from Bilbao to Donostia was not Renfe, it was Euskotren, which seems to be like a commuter railway or metro. So I didn't prebook my ticket, I just bought it from the machine at the train/metro station when I got to the station in Bilbao. (I started from Matiko station, the train also stops at Zazpikaleak/Casco Viejo station in Bilbao.) Important note: It looks like there is work being done on the train track from Zumaia to Donostia, so we all had to get off the train in Zumaia and get on a bus for the remainder of the journey to Donostia. (So if you're going from Donostia -> Bilbao and this work is still going on, you may initially board a bus at the Amara-Donostia station.) The Euskotren website is at https://www.euskotren.eus/en Please let me know if you have other questions!

Barbara, there are trains between Bilbao and San Sebastian (and the scenery's nice), but it's run by Euskotren rather than Renfe. The train makes a large number of stops and may take a circuitous route, because the trip takes about 2 hr. 40 min., or longer with a change at Zumaia.

https://www.euskotren.eus/en << Main webpage

https://www.euskotren.eus/sites/default/files/horarios/EuskotrenE1MatikoAmaraCARTEL50x70cmINVIERNO%202023_2.pdf << Schedule for line E1 between Bilbao and Donostia-SS.