Who loves Extremadura?

I do! I stayed in Caceres and visited Merida as a day trip. We mostly did outdoors things (by car) otherwise: Los Barruecos, Monfrague, and Alcantara (to see bridge and hike).

As a Basque local...I love Extremadura, the only thing they do not have is the ocean nearby, as per the rest...you´ve got it all!!

Extremadura is often overlooked and really underappreciated, in my opinion, it's one of Spain’s most fascinating regions and best kept secrets. It's full of time-warped old towns, castles, monasteries, and beautiful countryside, and was the homeland of many Conquistadors. And also the best Jamon Iberico in Spain comes from this region (imo) lol! I think mid-October should be ok weatherwise. You can fly in to Madrid, pick up a car, then head west into Extremadura. I'd recommend these places:

Cáceres (home base 3-4 nights): The old town of Cáceres is a UNESCO World Heritage Site and has a mix of Roman, Islamic, Gothic, and Renaissance styles.

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.

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.

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.

Mérida (home base 2-3 nights): Mérida is the provincial capital and has some of the best Roman ruins outside of Italy.

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".

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.

Monesterio: 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.

At the end you can finish in Sevilla, drop off your car, spend a few days in the city (or just keep going), before taking the AVE high speed train back to Madrid to fly out. Hope this helps :)

Extremadura is a great destination. In many places you will literally feel like you have stepped back in time. I have visited lots of places in Extremadura and often advise folks that it is a hidden gem not usually on the American tourist radar. Three of my favorite places were Cáceres, Trujillo and Guadalupe. All very worthy of your time and I would certainly go back there again. The ruins in Mérida are impressive but I was not impressed with the town itself. I did not get to Badajoz but it looks attractive. I also visited the Valle del Jerte with its 1.5 million cherry trees all in blossom. It is beautiful in the spring but if you are going in October you will miss this. I keep a running wish list of places I would like to visit in Europe, based on photos or videos or books that I come across. I have a whole list of very interesting small towns in Extremadura on that wish list. If you are travelling with a car you might want to consider exploring some of these: Hérvas, Granadilla, San Martín de Trevejo, Almendralejo and Mogarraz. The three times I have been to Extremadura were by car and a car would be necessary to probably visit these small towns. I have a good friend who is from a very small town in Extremadura and travelling with her was my first introduction to the area.

Adding Béjar, all the Jerte valley, Granadilla, Hervás (amazing), Olivenza, Badajoz and the largest wall after the Chinese one...so many wonderful, unspoilt places!

We’ve been there a couple times going back to 1979 and are going back later this year for just over three weeks. During that time we’ll stay in a relatively small area roughly bounded by Madrid-Plasencia-Mérida-Almagro. Other than Madrid we’ll be staying at Paradors in Toledo, Gredos, Oropesa, Jarandilla de la Vera, Plasencia, Trujillo, Guadalupe, Cáceres, and Almagro. Upon arrival we are picking up the rental car at the airport in Madrid and driving the hour to Toledo where we’ll spend two nights. Since we’ve been to Toledo six or so times, we’re only going there to get over jet lag.

From those locations we’ll take day trips to places such as, Monasterio de San Jerónimo de Yuste, Hervás, Granadilla, Arenas de San Pedro, San Martin de Trevejo, Coria, Monsanto (Portugal), Talavera de la Reina, Alcántara, Monfrangüe, Natural Monument Los Barruecos, Templo Los Mármoles. Embalse de Valdecañas, and a few other sites. On last year’s trip we also visited Ciudad Rodrigo, Béjar and El Barco de Ávila. Some places I mentioned were mentioned by others.

Mogarraz, mentioned by Pat, as well as nearby La Alberca were very much worth visiting. A car is needed to visit them.

Extremadura is so special and wonderful! It was my favorite area in Spain. We did not get to see as much of it as I would have liked (reason to come back) but Cáceres was such a joy and so unspoiled. I'm almost hesitant to recommend it because I'm really afraid that it will become the next "back door" place and start gaining huge crowds.

(although La Alberca is not in Extremadura, but in the neighboring province of Salamanca, part of Castile and León). Worth the visit, really.

To be even more specific. Mogarraz, La Alberca, Ciudad Rodrigo, Béjar, and El Barco de Ávila are all in the region of Castilla y León, but not far from Extremadura. Toledo and Almagro are in Castilla y La Mancha.

Thanks to the OP for asking the question and all those who replied, great information for planning my next trip!

Love Extremadura. Try to include Jarandilla de la Vera..nice parador there...

Awesome area that’s still a back door. Sign up for a free Paradores membership if you want to stay in fantastic historic buildings with really good food

A quick clarification about Paradors. While many are in historic buildings not all of them are. What the free Paradors membership gets you is a reduced price when reserving through its website and a free welcome drink (beer, wine, soda) ever time you check into one.