On this trip, other than Madrid, we stayed at Paradors and had a rental car. We started in Toledo and then stayed in Gredos, Oropesa, Jarandilla de la Vera, Plasencia, Trujillo, Cáceres, Guadalupe, Mérida, and Almagro. Other than in Mérida we found free parking near the hotels if it wasn’t free at the hotel. In Cáceres, because the hotel is within a pedestrian only UNESCO Heritage site, parking was further away.
Temperatures were mostly in the low to mid-sixties during the day and into the fifties at night. There were a few days when it rained, but only one that affected what we planned to do.
The only times cash was needed was when we bought cookies at a convent in Toledo, the Monastery in Guadalupe, and at laundromats in Plasencia and Almagro. There was one legitimate occasion when the Internet went down at the cafeteria by our hotel in Madrid, so we paid in cash rather than wait for it to come back online. It was online the next day. While I did use cash for many small purchases it was by choice. All credit card purchases were contactless. The hotels gave the USD or Euro option without having to decline the DCC. With a couple exceptions all other places automatically charged in Euros.
I used one ATM machine in Toledo to take out a small quantity of Euros to top up what I had remaining from a previous trip. Throughout the trip I did notice some ATMs had a contactless option, but I have no idea if it worked with U.S. credit cards.
With the rental car I purchased fuel from manned stations. I honestly didn’t notice any unmanned stations. At most stations attendants pumped the gas for you and you paid inside. There are rural locations where fuel stations are few and far between, so for those considering renting a car, ensure you have enough fuel to get you to the next town or two. During one stretch on this trip I drove for almost an hour without seeing a station.
Outside of the main tourist destinations it was difficult to find a restaurant to get food between 4:00pm and 8:30pm. Many restaurants were closed on Mondays while others were closed on Tuesdays. Due to the region we visited pork and paprika featured prominently on menus.
Having been to Toledo numerous times we just walked around the town and didn’t go into any of the standard tourist sites. It was a place to get over jet lag. Between Toledo and Gredos were stops at Guadamur, Arenas de San Pedro, and Mombeltrán to see castles. Gredos is up in the mountains and a nice place for hikers. There are no towns of any size nearby.
After Gredos there were stops at the Marbles Temple on the Valdecañas Reservoir and Belvis de Monroy castle en route to Oropesa. In Oropesa we had a room that looked out at the town castle; the only real site to visit in town. Between Oropesa and Jarandilla de la Vera were stops at Madrigal de la Vera to see a Roman bridge, Devil’s waterfall, Valverde de la Vera (on Spain’s prettiest village list), and Villanueva de la Vera (some architecturally nice buildings). From Jarandilla we visited nearby San Jerónimo de Yuste Monastery, and the villages of Cuacos de Yuste and Garganta la Olla.
Between Jarandilla and Plasencia were stops to visit the castle and abandoned town at Granadilla and Hervás to see the medieval bridge and Jewish quarter. In Plasencia we visited the cathedral and walked along a portion of the old town walls. From there was a day trip over to Monsanto Portugal to see the landscape and some filming locations used in House of the Dragon. Returning from there were stops in Coria and Galisteo to see another medieval bridge, castle, and walk along more medieval town walls. Unlike most walled towns, the walls at Galisteo were built river river stones rather than the blocks.