“If you want to go traveling in Spain,” an old timer might say, “well, wander through the stone cities of Castilla. Explore the greens hills of Andalucia. Bury your feet in the sands of Catalonia, but don’t go beyond the Douro. Out there, there be dragons.”

OK, maybe I’ve watched Pirates of the Caribbean one too many times, but there’s no doubt that for much of it’s history Extremadura was a wild and woolly place. The very word, meaning beyond the Douro River, implies an unknown, mysterious land.

At the far western edge of Spain and bordering Portugal, Extremadura is historically the poorest region in Spain, and remained so right up into modern times. Rolling green hills hide deceptively thin soil. The main products seems to be acorns and rocks.

It was from this region that many of the conquistadors sailed off to conquer the new world. Well, first they had to ride or walk to reach the sea, but think about what the recruitment posters for this little venture must have been like.

Meet new people! See new lands!
Fabulous riches await!*
*If you survive. Chances of surviving the sea voyage: less than 30%; odds of being killed by a native after you arrive, greater than 50%; death or permanent disfigurement by unknown disease: 20%; likelihood of ever returning home, well, let’s not go into that.

Those who signed on were either incredibly bored or had absolutely nothing to loose.

Today Extremadura is on the map as one of the best producers of jamón ibérico, sort of the Spanish version of prosciutto (remember all those acorns; pigs love them). The region is also home to some beautiful, authentically old world villages and some of the best Roman ruins anywhere in Europe.

Mérida

The Roman city of Augusta Emerita was established by the Romans in 25 bc as a major stop on the Via della Plata (Silver Road). Along this route, silver mined in Northern Spain was hauled down to Sevilla, where it was loaded onto boats and sent back to enrich the coffers of the Roman State (and quite a few Roman governors, including Julius Caesar).

At its peak Mérida was one of the biggest and most important Roman cities in Spain. Because of the growing silver trade, and the town’s strategic position on the cross roads of two major trade routes (the other running from Toledo to Lisbon), it soon became the capital of the Roman province of Lusitania.

The city today is a modern, dumpy mess and would be worth detouring to avoid if it weren’t for the most fabulous collection of Roman ruins anywhere in Iberia.

Cáceres

A lively university town and the main commercial and transportation hub for the Extremadura region, Cáceres never the less manages to maintain a small town appeal. This is in part due to its compact, well-preserved old town, a very nice example of Spanish Renaissance architecture. Ignore the expanding modern city and limit yourself to the Ciudad Monumental within the town walls.

Trujillo

One of the most attractive towns in the Extremadura region, Trujillo is a perfectly preserved Renaissance city. The town was birthplace of many of the conquistadors, including Francisco Pizarro, who defeated the Incas. Monumental but stern mansions and public buildings make up the center of the town, built on the wealth plundered from the Americas.

Guadalupe

It’s hard to imagine a more beautiful setting for a monastery, isolated from the outside world and surrounded by rugged mountains. The monastery was built on the sight where a shepherd found a carving of the Virgin Mary, rumored to have been carved by St. Luke. From the 14th century on it became one of the most important pilgrimage sights in Spain. It’s location in Extremadura ensured that it received a steady stream of offerings from conquistadors returning from their adventures, all loaded down with New World wealth. Sacked by Napoleon in 1808, the monastery was abandoned for over 100 years, but has been cared for by a group of Franciscan monks since the 1930s.

Tags: Cáceres, Extremadura, Guadalupe, Mérida, Trujillo