This itinerary assumes a driving loop from the Madrid area. Be warned that Extremadura can be extremely hot in the summer (it is called the "frying pan of Spain") and you may wish to travel at another time of year if possible.
- Leave Madrid by 9 am
- Detour via Monte Venus, a large hill just south of the Sierra Guadarrama, for a splendid view
- Descend the hill to the old town of Talavera de la Reina, spend 2 hrs
- Drive to Guadalupe, spend the night. This should allow you plenty of time to explore the town in the late afternoon/early evening.
- Leave Guadalupe by 10 am
- Drive to Trujillo, spend 4 hrs exploring thoroughly
- Drive to Caceres, spend the night
- Spend the morning exploring the historic old center of Caceres (a UNESCO World Heritage Site), leave by 1 pm.
- Drive to Monfrague National Park, spend 1 hr. There is a ruined castle as well as a couple of panoramic overlooks.
- Drive to Hervas. Spend the rest of the afternoon & evening enjoying this tranquil little town.
- Leave Hervas by about 10 am.
- Drive to Candelario, spend about 3 hrs
- Drive to Bejar (the ultimate origin of the name of Bexar County, home of San Antonio, Texas, U.S.), spend 45 mins
- Drive to Mirador de Lobos, spend about 30 mins
- Drive to La Alberca, spend the night
- Spend the morning enjoying the picturesque town of La Alberca, leave about 11 am
- Descend the steep escarpment into the Las Hurdes region. Wind through the area, taking at least 1 hr to enjoy views and quaint little towns along the way.
- Drive through the Valle del Jerte, spend a few minutes at the mirador in the center.
- Drive to the town of Bonilla de la Sierra, spend 45 mins
- Drive back to Madrid
Enjoy the trip!