Portugal with a dip into Spain. Opinions wanted.

Of the place you mentioned I've only been to Merida. The reasons to go there are certainly the Roman ruins and the archaeological museum. I am a fan of mosaics, and the museum has some nice ones. Otherwise, Merida isn't a particularly great destination; I'm a fan of just walking around and looking at interesting architecture, and Merida frankly is very lacking on that score.

Also in that part of Spain, I stayed in Caceres and really enjoyed wandering around its large historic area. It's an amazingly nontouristy city, given its atmosphere. I give it a very high recommendatio. Trujillo, which was home to several Spanish explorers, is also worthwhile, but it's farther from Badajoz and Merida.

Much as I wasn't entranced by Merida, it might be more convenient as a base than Badajoz if you have several days for sightseeing in that area and want to see Caceres/Trujillo as well.

Be aware that Caceres, Merida and Trujillo are likely to be very hot in the summer. I'd guess that condition also applies to Badajoz and Elvas, but I haven't researched their weather patterns.

Carole - What a great trip you’re planning! Our trip 19 (!) years ago was a trip to Spain, with a dip into Portugal, and unfortunately didn’t include those locations, but for what it’s worth: Are you planning on driving between those countries? We flew to Spain, then after a couple weeks, flew to Lisbon, and rented a car there.

After driving to destinations north and east, we headed back to Spain for a final week, turning in our rental car in Spain. Although Hertz charged a hefty fee for a one-way rental to a different country, it was easier and cheaper than trying to do separate rentals in each country, and try to cross the border with separate rentals involved. If you’re starting and finishing in the same country, that large fee wouldn’t apply, but I wanted to mention it.

Caceres sounds and looks incredibly tempting!

What attracts you to Badajoz? It has the very impressive alcazar (castle), but otherwise it's a fairly nondescript city, sprawling and not somewhere I'd especially plan to stay overnight for any "vibe". Since Badajoz and Elvas are only about 25 minutes drive apart across the border, I don't think Badajoz' notional central position makes any real difference. I'd certainly pick the very interesting Elvas to stop in overnight if chosing between those two. Elvas is something of a small gem of a place.

However, Merida (by contrast with Badajoz), is great and well-worth an overnight or two. I don’t know the rest of your itinerary, but could you stay in Merida, then return to Elvas/Portugal, with just a quick visit to Badajoz along the way for the castle? Or vice versa?

If you have enough time and it fits your overall route, you might consider Caceres as well as Merida - perhaps stopping in one town and day-tripping for the other? Caceres is worth a couple or more of (relaxed) days. I think Caceres is a little more attractive/interesting than Merida (especially Caceres' atmospheric walled old-town part and the plaza Mayor just outside those walls). Whilst I like them both, in a choice between Merida or Caceres, I'd chose the latter (unless you have a particular Roman interest).

I know this is just a quick visit to Extremadura, but there are a few other places worth considering convenient for driving routes around border. For example charming Olivenza which is now on the Spanish side, but only a couple of centuries ago was Portuguese (it is about 15 miles from Elvas). There are many other good places to visit in Extremadura, of course, but I suspect some in the eastern half would be too far from the border for this visit.

What's nice about Cáceres‎ is that it's full of architectural eye candy, due to a fine mix of Roman, Islamic, Gothic, and Renaissance styles in the old town, which has since been designated UNESCO World Heritage Site. On Mérida, its Roman sites are quite magnificent, but they are spread throughout the city and not centrally located as other historic sites tend to be, that will need to factored.

Know that Cáceres‎ and Mérida are but one part of the Extremadura region of Spain, a really fascinating and historic place that is very much under the international tourist radar. You could also consider a daytrip to Zafra, a white-washed walled town, located in the province of Badajoz, and nicknamed the "Little Sevilla" due to its preserved Moorish architecture. They filmed some scenes from the T.V. show Game of Thrones at the nearby Castillo de Feria, a Moorish hilltop fort.

I agree wholeheartedly with acraven's recommendations. Like her, I very much enjoyed the Roman ruins of Mérida but did not find the city itself so appealing. We did a daytrip there. I have not been to Badajoz. Please consider a stay in Cáceres right in its historic center. It is stunning and a great place to wander and explore. Trujillo was also impressive, a step back in time. We stayed overnight in Trujillo, and the main town plaza at night is eerily spooky. Extremadura, Spain is beautiful and full of many smaller towns that are usually not as heavily touristed as the rest of Spain, but full of history and local color.

I love this forum! So now, after reading all of the above replies, I will absolutely put Caceres on my list, and I will eliminate Badajoz and even Merida. Not to be blase, but I have seen Roman ruins aplenty all over Europe and Caceres looks picture perfect. It is not far out of the way (I will be coming from Tomar, and after Caceres heading to Elvas.) I will still be dropping the car off in Portugal, so hopefully that won't be an issue. I figure, in response to Chani, that the potential drop off fee for a one-way within Portugal car rental will be reasonable for the convenience, considering our itinerary. My new Itinerary: fly into Porto 3N, rent a car upon leaving Porto, drive to Braga 3N (for daytrips). 2N on the Douro near Regua. Drive to Coimbra 2N. Drive to Tomar 2N. Drive to Caceres (3N??),
Drive to Elvas 2N, Evora 3N. Drop off the car, train to Lisbon, train to Sintra 3N. Train to Lisbon 5N. Fly home.
Still tweaking, since there is still uncertainty about travel and vaccines and all the rest. Thanks for all of your responses, and keep them coming!

My new Itinerary: fly into Porto 3N, rent a car upon leaving Porto, drive to Braga 3N (for daytrips). 2N on the Douro near Regua. Drive to Coimbra 2N. Drive to Tomar 2N. Drive to Caceres (3N??),
Drive to Elvas 2N, Evora 3N. Drop off the car, train to Lisbon, train to Sintra 3N. Train to Lisbon 5N. Fly home.
Still tweaking, since there is still uncertainty about travel and vaccines and all the rest. Thanks for all of your responses, and keep them coming!

Would you consider reversing the order? It's easy to get to Sintra from the Lisbon airport by uber or taxi and not expensive. Sintra is small, so it's a better place to recover from jetlag. Then uber to Lisbon, get the car and drive to Evora. . . . finally drop the car when you get to Porto. Consider giving Porto one more night. If you stick with your current plan, you might as well drive to Lisbon airport to drop the car and then uber to Sintra. I think I paid about €30 from Sintra to Lisbon and the price quote was about the same for central Lisbon and the airport. Just avoid rush hour around Lisbon - a.m. into town, p.m. out of town.

If you were going to Porto and the Douro Valley in Northern Portugal, you should visit Salamanca and Santiago de Compostela in Spain. Salamanca is east of the Douro Valley and Santiago is north of Porto.

"Would you consider reversing the order? It's easy to get to Sintra from the Lisbon airport by uber or taxi and not expensive. Sintra is small, so it's a better place to recover from jetlag." I will consider anything. But note, we will likely be arriving in Portugal from within Europe, so no jetlag to worry about. I thought starting in the north and ending in the Lisbon area eliminated the need for a "loop" and also it's much easier to fly back to the States from Lisbon (most flights from Porto first stop in Lisbon.) As far as Salamanca Santiago di Campostela, they are a little too far afield to fit into this trip, as worthwhile as they undoubtedly are. So much world, so little time.

The drive between Tomar and Caceres is about 3 hours. You might want to include a refreshment/comfort break at Alcantara which is about two-thirds of the way along when coming from Tomar. Alcantara's top sight is the impressive bridge (nominally Roman, but damaged and rebuilt so many times it is a bit of a stretch to say it's really Roman now). The town above the gorge is attractive, with mediaeval sights worth a visit. There may be tolls on the Portugese leg of this route.

I see you've dropped Merida, but the drive from Caceres to Elvas could take you right past the city, so you might have time to pop in for a few hours to see some of the remains?

Great idea about Alcantra because 3 hours in the car deserves a break!