This itinerary is written as a driving loop from the Madrid area. Note that this itinerary also includes one night in the province of La Rioja, but is all under the category of Castilla y Leon for convenience.
- Leave Madrid by about 9 am
- Drive north through the Somosierra Pass to El Burgo de Osma. Spend 1.5 hrs seeing the castle and Celiberian ruins.
- Drive to Gormaz, spend 1 hr seeing the castle, the largest in Spain.
- Drive to Berlanga de Duero, spend 1 hr.
- Drive to Soria, spend the night.
- Spend the morning exploring the architecture of Soria, leave by about 12:30 pm
- Head to the ruins of Numantia, a Celtiberian fort just north of Soria; spend 1 hr
- Head north into the Sierra de la Demanda, then west on very winding back roads. Take some time to admire the natural beauty and tiny villages.
- Arrive in the hamlet of Pineda de la Sierra about 6 pm, spend the night in a "casa rural" like El Hayedo.
- Spend the morning hiking on the Via Verde de la Sierra de la Demanda, which runs right by Pineda de la Sierra at the Ermita del Santisimo Cristo, leave by 12 pm.
- Continue driving through the mountains to Santo Domingo de la Calzada, spend 1 hr seeing its cathedral.
- Drive to San Millan de la Cogolla, arrive about 3:15 pm. This is a UNESCO World Heritage Site with two famous monasteries (Yuso and Suso) in which the earliest written records of the Spanish language (as opposed to Latin) were recorded. The monasteries have odd hours; Yuso is open from 10-1 and 3:30-5:30 and Suso is open from 10-1:30 and 4-6, so see Yuso first. If you get to Yuso when it reopens at 3:30, you will have 2.5 hrs to see both.
- Spend the night in San Millan de la Cogolla or in one of the several adjacent small towns like Estollo, San Andres del Valle, or Berceo.
- Leave San Millan by 9 am.
- Drive to Frias. This route takes you slightly out of the way but through a very scenic canyon on the Ebro River. When you cross the Ebro, you are actually very briefly in the Basque Country.
- Frias is a gorgeous walled town perched on a hillside with a castle and "casas colgadas" (hanging houses) like Cuenca. Spend about 3.5 hrs.
- Drive to Burgos, spend the night.
- Burgos has a beautiful Plaza Mayor & Cathedral, as well as an interesting textiles museum in a monastery. Spend the morning and first part of the afternoon exploring this great city; Leave about 1 pm.
- Drive to the extremely cute and quaint Covarrubias, spend 2-3 hrs.
- Drive to Santo Domingo de Silos, spend the night. I recommend the Hotel Tres Coronas de Silos, which has a fantastic restaurant.
- In the morning, go to the abbey in Santo Domingo de Silos to hear the famous monks chant, then tour the abbey. Leave by about 11 am.
- On the way back to Madrid, stop by the palace of Manzanares el Real, spend about 1.5 hrs.
Enjoy your trip!