Spain/Portugal 2 week Itinerary help for May 2019

I cannot help at all on the car issue.

You're proposing to head in all different directions to hit a single place when there are other spots in the area that I believe you'd enjoy just as much, or even more. I'd suggest digging into a comprehensive guide book and limiting the number of regions you visit so you can have a more in-depth visit.

If you go to San Sebastian, it's a real shame to skip Bilbao, which has a larger and much less touristy historic district. Vitoria-Gasteiz, Hondarribia, and a number of small coastal villages are also worthwhile stops.

Merida has some Roman ruins and a nice archaeological museum, but the towns of Caceres and Trujillo are more atmospheric.

If you get to Zaragoza with a car, try to go on to Teruel (regional capital but so off the beaten path that you may be the only non-Spaniards in town) with its mudejar towers and bits of early 20th-century architecture. Once in Teruel you're relatively close to Cuenca, which has a medieval upper town and hanging houses along a gorge. I've always wanted to go to the village of Albarracin, which is in that area (west of Teruel) but inaccessible without a car. It's less than a 1-hour drive from Teruel if ViaMichelin can be believed.

To go to Seville and skip Cordoba would be a rather odd decision, and there are the white towns to explore as well.

You may be underestimating the travel time between your targeted spots as a result of having used the very fast AVE trains in the past. Those trains are at least twice as fast as driving. Consult ViaMichelin.com to see how long it will take to drive to Seville and San Sebastian. You'll chew up more than half a day going to and from those locations (measuring from Madrid). That's another reason why I question the appropriateness of going all the way up to the Basque Country (for one example) just to spend a day in San Sebastian.

Do you really want to travel to Catalunya just for a repeat visit to Montserrat?

To be clear: Many of the target destinations on your itinerary do not have AVE service (though Seville and Zaragoza do), so your choice will often be between slower trains/buses and driving. Driving will probably not be slower than public transportation for San Sebastian and Merida.

Hi Suze, I think you may be on to something here, since you are considering Mérida, maybe you can also consider a road trip through Extremadura as a whole?

The often overlooked and underrated Extremadura is, in my opinion, one of Spain’s most fascinating regions. It is full of time-warped old towns, castles, monasteries, and beautiful countryside. It is the region bordering Portugal to the west and was the homeland of many Conquistadors. For a potential road trip I would do something along these lines:

Start In Madrid drive to Cáceres
-Day 1: Cáceres: The old town of Cáceres is a UNESCO World Heritage Site and has a mix of Roman, Islamic, Gothic, and Renaissance styles.

-Day 2: Parque Nacional de Monfragüe: Day trip from Cáceres to this biosphere reserve, includes stunning cliffs & rock formation, plus many kinds of wildlife (especially noted for its Griffon vultures). Has some really great hiking trials.

-Day 3: Trujillo: This town is where some of Spain’s most famous(infamous) conquistadors came from. The town has a few baroque and Renaissance palaces and an interesting Museum of Francisco Pizarro, who led the expedition that conquered the Inca Empire.

-Day 4: Guadalupe: Has the beautiful Real Monasterio de Guadalupe. You can tour this monastery and its collection of art, jewels, illuminated manuscripts. You can also see two cloisters, one late-14th-century Mudéjar, the other Gothic.

-Day 5 and 6: Mérida: As you probably know Mérida has some of the best Roman ruins in Spain, I would actually spend two days there.

-Day 7: Zafra: On the way to Zafra stop by Castillo de Feria, an originally Moorish hilltop fort. Zafra itself is a white walled town nicknamed "Little Sevilla" and feels very "Moorish".

-Day 8: Jerez de los Caballeros: A very picturesque small town. The old town is surrounded by a Moorish wall with six gates. After it was conquered from the Moors, the town was transferred to the Knights Templar, who left their own architectural mark.

-Day 9: Monesterio: Finish your trip at Monesterio which is an unassuming little town that produces some best Jamón ibérico in all of Spain. You can find the real Museo del Jamón there, not those touristy ones you will find in Madrid.

End trip - Drive down to Sevilla (about an hour south of Monesterio).

Thank you, Carlos. My son loved the ruins in Ostia Antica outside of Rome ( it was his favorite day trip) and we have seen it twice. So, I will be hitting google to investigate this itinerary because it sounds just like what I was looking for.

Thank you, ACraven. We visited Bilbao a few years ago and loved it and didn't have time to see San Sebastian which was the main reason for the return to Basque country so will likely forego it again. I don't speak Spanish but watched an international movie on Netflix, (I think it translates to "Eight Basque Surnames") and it fueled my desire to visit Spain.
I have wasted a lot of time on trains/plains losing entire days just traveling. You have given me valuable advice to not rush through these lovely cities/towns.

Hi Suze, yes the film you are referring to Ocho Apellidos Vascos was quite the phenomenon here in Spain. Interestingly the film was able to unite Spain (for a bit) when it first came out. Because it revolved around a love story between a guy from Andalucía and a girl from the Basque Country (complete opposites), it represented the hope that the different ethnic groups of Spain could set aside their differences and come together. Unfortunately this reality seems to become more and more distant with every passing year.

Your list is really too long. Probably best to choose either Mérida or San Sebastián. This is quite a rush with long travel days.

Start in Barcelona - 3 nights
{visit Tarragona or Montserrat}
Train to Zaragoza - 1 night
Train to Madrid - 3 nights
{visit Toledo & Segovia}
Train to Merida - 2 nights
Train to Seville - 3 nights
Fly to San Sebastián - 2 nights