Originally a fortified Roman camp, this historic university town with narrow cobblestone streets and buildings carved from a unique golden stone is an architectural delight. The town used to be a summer resort for Madrid's wealthiest families, and it retains an air of propriety. Plaza Mayor, surrounded by four-story buildings with baroque ironwork, is one of the most beautiful in Spain (and, until 150 years ago, the site of bullfights). Outdoor cafes surround the square, and the streets that lead from it have great shopping (especially clothing and shoe boutiques). Visit the side-by-side Romanesque Catedral Vieja and the Gothic Catedral Nueva (New Cathedral—built 1513-1733), as well as the 15th-century Casa de las Conchas (the House of Shells—covered with skillfully carved seashells, grillwork and coats of arms).
The focus of the town, however, is the university, which was founded in 1215 by Alfonso IX. The 16th-century facade is a virtual flea market of decoration. According to legend, those who spot the frog on one of the three carved skulls the first time they look will always have good luck and be married within the year. Salamanca hosts a weeklong fiesta in September that includes parades, outdoor music, street dancing and bullfights.
A bit southwest of Salamanca toward the Portuguese border, the old military post and walled city of Ciudad Rodrigo is worth a night's stay. Set on the banks of the Agueda River, it's a fun town to explore: See the eight city gates, walk through its narrow and winding streets, and tour the 12th-century cathedral and 15th-century Palacio de los Castro (a beautiful home). Stay at (or at least visit) the Parador Nacional de Enrique II, a castle that's been converted into a hotel. If you're there during Carnival, you can watch the fighting bulls run through barricaded streets. Salamanca is 130 mi/210 km northwest of Madrid.