Madrid was a dusty hamlet beside the shallow Manzanares River when Felipe II decided to make it his national capital in the 16th century. He thought its position at the center of the peninsula would help him control the fractious former kingdoms at the periphery. While it is younger than most of Europe's major cities, Felipe's successors lavished Madrid with art and monuments, making it the guardian of the national patrimony. Sample the results in the Archeological Museum, with its serene Dama del Elche, the bust of an Iberian princess rendered five centuries before Christ, and in the Reina Sofia Museum, which contains Picasso's epic mural, Guernica.

Allow a bare minimum of three days for Madrid–we represent dozens of hotels in the city, and can help you choose between grand hotels and smaller, more intimate retreats. After Madrid, drive northwest toward El Escorial. This tidy town exists because of the brooding royal palace-monastery of the same name built at the bidding of the reclusive Felipe II. It deserves a long visit, especially to his prodigiously decorated apartments, chapel and library.

After lunch in town, continue in the same direction, soon turning west toward Ávila (see hotels). What a site it is, the highest provincial capital in Europe, surrounded by massive walls incorporating 90 watchtowers dating from the 12th century. This medieval city was the birthplace of Saint Teresa, founder of the Carmelite order. A 16th-century palace backed into the walls is now the Parador Raimundo de Borgoña. Its dining room is the place to try the heavenly local dessert, yemas de Santa Teresa–candied eggs. Work them off afterward by mounting the ramparts and following the walkway along the top.

Parador de Avila

Leave early the next day, for Salamanca (see hotels) is only an hour away, and it's arguably the most engaging town in the old kingdom of Castile. Built of honey-colored stone, its university is one of the oldest in Europe and its main plaza is surely the most pleasingly harmonious than any in Spain. The "new" Gothic cathedral dates from 1513, while the Romanesque "old" one, from the 12th century, leans against it. Several portals are embellished with ornate carvings featuring dragons, saints, animals, and, in one restored part, an astronaut on a space walk.

On the opposite side of the Tormes River is the contemporary Parador de Salamanca (see hotels), which has its own swimming pool. You'll be reluctant to leave, but the next overnight is only about 140 miles south. Along the way, you can turn into Plasencia for lunch and a walk through the diverting old barrio (quarter) around the cathedral. Watch for the storks that inhabit large nests atop towers and chimneys for much of the year.

Finding the parador in the old town of Cáceres (see hotels) is a challenge, but worth the effort. The Parador de Cáceres is a 14th-century mini-palace with interior courts and a splendidly decorated dining room serving food characteristic of the Extremadura region. Right outside the door is an area of narrow, pitched streets bordered by mansions owned by Renaissance noblemen; they are surrounded by walls erected by the Moors.

Avila

Take your time poking into the shaded nooks of Cáceres because your next destination, Mérida, is barely 40 miles south. Mérida, a western outpost of the Roman Empire, was founded in 25 BC. Much of that era remains, including a magnificent theater with colonnaded double-tiered stage, villas, a forum, and an amphitheater in which chariot races and mock sea battles were held. In the center of the modern town is a former 18th-century monastery that is now the Parador Vía de la Plata. It has a pool and--rare in paradors--a fitness room with sauna.

Proceed toward Badajoz, a frontier town that spent time over two millennia as pawn or stronghold for the Romans, Moors, French and English. Reached by several bridges, some of them wide enough only for one oxcart at a time, its old sections are intriguing. From here, it is less than three miles to the Portuguese border.

Your night's destination is Estremoz, a fortified town rising above the Alentejo plain. At the peak is a 13th-century castle that happens also to be one of the best units of Portugal's version of the parador system, the Pousada da Rainha Santa Isabel. Because it's also one of the most popular, you'll need to book it well in advance. Materials like velvet, marble and gold leaf are generously employed and furnishings are either antiques from the Renaissance period or accurate reproductions. There's a pool, an excellent restaurant, and 24-hour room service.

Linger awhile . . . pottery of the region is made and sold in Estremoz and the main square and nearby streets offer numerous photo ops. When it's time, oceanside Setúbal is only 85 miles away. Tradition insists that the city was founded by a grandson of Noah, but Romans were assuredly among the temporary inhabitants. They harvested sea salt, oranges, and grapes for muscatel wine, products that remain the foundation of the local economy. The place to stay is the Pousada de São Filipe, a converted 16th-century castle overlooking the Sado River. Sunset on the terrace is special.

Pena Palace in Sintra, near Lisbon

Then, Lisbon (see hotels). One of Europe's most economical cities, it is also one of the most fascinating. Sprawling over seven hills traversed by picturesque trams and venerable funiculars, the highest elevation is surmounted by a Moorish fortress where peacocks and geese wander at will.

In the Alfama quarter below, the singing of caged birds echos down the cobblestone streets. The close-in suburb of Belem has monuments and museums celebrating Portugal's prominence in navigation, leading all Western nations in explorations of Africa, the Indian subcontinent and the Far East. In downtown Baixa and around the Rossio square, brush elbows with the natives in the little standup bars pouring jolts of cherry ginginha.

Itinerary 1
Barcelona to Madrid: Artistic Catalunya and the Pyrenees

Itinerary 2
Madrid to Lisbon: Across Old Castile to the Ocean

Itinerary 3
Madrid to Santiago: Heroes and Saints on the Way of St. James

Itinerary 4
Madrid to Seville and Granada: The Glories of Andalucía