Explore the UNESCO World Heritage Sites of Spain and Portugal

On your first full day in Spain, you’ll uncover two more expressions of history with a morning amid the royal landscape of Aranjuez and an afternoon embracing the medieval mystery of Toledo. The morning will focus on the details, as a private guide narrates the artistic story that accompanies a landscape of regal excess. Toledo will be the first of many cities on your trip that is entirely protected as World Heritage Sites, and the harmony of architecture will be as impressive as the preservation of time. Take a walking trail through the narrow labyrinthine streets where churches are decorated by El Greco’s finest work and spires act as compass points. Then, you’ll return to Madrid for another evening at one of the city’s plazas.

Avila’s thick white walls suggest a time of conflict, redolent of an era when war was rife on the plains. The city behind the walls is cute and white, easy to walk around in only an hour but full of details that make you linger. You’ll travel here on the high-speed train, and disembark to meet a local guide who will escort you around the city. Spend the morning on a relaxed guided tour before you end with a typical Castile lunch at a superb local restaurant. In the afternoon, you’ll board the train to Salamanca, the city of golden sandstone. When you arrive, you’ll wander around the city at your leisure and marvel at the copious old center.

A Romanesque cathedral’s spires lean with age, which is juxtaposed by the Gothic design of an adjacent newer cathedral. Close by are some of the great early Gothic works such as the university facade and Casa de las Conchas. As you continue walking, you’ll pass a Renaissance facade to reach the Baroque Plaza Mayor. All of the buildings will be the same color but a different era. For an easy journey through Europe’s architectural design, there are few places like Salamanca. End the day at a great little wine bar-restaurant booked by your guide.

Today you’ll explore Bejar and Hervas, two tiny Spanish towns that are ideal for walking the lanes of history. Very few tourists come here and the locals on the streets still dress a little like the medieval era. On your route to Caceres, this stop will break up your journey across the wild open plains of western Spain. Then, arrive in Caceres for lunch, and dine at a decadent restaurant that serves the cuisine of the Extremadura region. Relax, and take your time, as you feel the medieval pace rub off. This is a city for walking slowly, a city where time isn’t dictated by the clock, It’s a mysterious place that has stayed off the beaten track, despite the long-time UNESCO status. The guide will take you on an orientation tour, where you will dip into the finest villas and monuments among the protected center. The evening is at your leisure.

The next day, you hear footsteps echo along lanes of cobblestone and allure while church bells chime in harmony. Winding streets seem to lead you in the opposite direction to what you were expecting. There is no traffic, no motorized noise from the 21st century. Caceres is one of Spain’s lesser-known gems, the traditional capital of the country’s most traditional region. You will have a full day at leisure and the beauty of the city comes from exploring without a map. Don’t miss the food, as Caceres is the best place in the world to eat black Iberian ham. Also, be sure to visit the quaint squares, where locals meet to drink coffee and wine, just like they have done for centuries.

Today you’ll explore a different side of Spanish history. Merida is home to some of the finest Roman ruins outside Rome. There’s an Amphitheater that is iconic and expressive in its shape and two tiers of columns resist the urge to crumble. There’s also an excellent museum full of artifacts that have been dug up in the area. Yet, Merida isn’t purely about the monuments. The World Heritage area incorporates a ninth-century Islamic fortress, along the Roman bridge, and the mosaic floors of early settlements. Like Caceres, there is a living history here, one with many chapters to be told by your local guide. After you arrive in the early morning, you will have a full day in the city, which will be your last destination in Spain.

This morning, as you leave Merida you’ll see that this city has always straddled a frontier. Travel west to Evora and you’ll find an old Portuguese town that has a palatable frontier atmosphere. Hiding behind thick medieval walls you find rows of townhouses, then a Roman Temple juxtaposed with the spires of a 12th-century cathedral. With one of the best-preserved historic centers in Iberia, Evora effortlessly creates the feeling of bygone centuries. Enjoy an afternoon walking tour of the city before you embrace Portuguese cuisine and customs in the evening.

When Vasco de Gama set sail around the world and returned to his home country with treasures, Portugal crafted a distinct architectural style in celebration. Architects incorporated influences from French Gothic, Italian Renaissance, downtown Flemish, and Spanish Plateresque into their design. This style became known as Manueline, with the finest two examples of the architecture found in the riverside Lisbon neighborhood of Belem. Today, with a skilled guide you can pinpoint the differing influences, especially at Jeronimos Monastery. This detailed morning is followed by an afternoon watching the city roll by on a tram tour that connects Lisbon’s neighborhoods.

This morning, strange chimneys emerge from a royal palace while another palace is painted pink and a third is cast in yellow. Sintra is a landscape of regal buildings with more than 1200 years of history. To this day, historians debate when the palaces were built as it occurred at a time before written records in this part of Iberia. Explore this fairytale world, while you recall the words of poet Lord Byron. As the tour buses arrive, you’ll leave to spend the afternoon on the coast. Cascais is a lovely Atlantic Ocean resort town from the late 19th century. With lunch at a legendary seafood restaurant, this will be a very relaxed place to spend the afternoon.

On your way to Batalha, you’ll stop in Obidos, a fortified village where every street feels medieval and a Moorish castle casts a shadow on the cobbled main square. Then, visit Alcobaca where a towering 12th-century church showcases the earliest Gothic style. Once you arrive in Batalha, discover the monastery, which is a stunning example of late Gothic excess, built at a time when architectural boundaries had been eroded. Comparing the World Heritage buildings in Alcobaca and Batalha is the best way to appreciate how the Gothic style changed over three centuries. You’ll spend the night in Batalha, beneath the curious eyes of statuesque ghouls and the sense of tradition for which the city is famous.

The following day, you weave across the hills to Porto, the most beautiful of Portugal’s old cities. Like most nights on this itinerary you’ll stay within the World Heritage center, surrounded by the carefully preserved styles of the past. Ceramic mosaics are everywhere, which narrate historical scenes through art. Palaces and churches reflect Baroque glamor, magnificent symbols that stand beside picturesque corners. Spend the morning in the city, visiting the most famous of the buildings in the old central neighborhood. Then spend the afternoon on the river, as you cruise up the Douro before you take a tour of one of the Port cellars that stands on the water’s edge where you will taste various vintages.

Braga and Guimaraes are fine expressions of the Middle Ages and cradles of Portuguese civilization from the time of independence. Today, you admire the majestic cathedral in Braga then wander the Baroque stairway. Discover the Palace of the Dukes and the castle that preserved early Portuguese identity. These two cities are close to Porto and the pace of today’s tour is very relaxed, which will leave plenty of time to discuss history and heritage with your expert local guides. Like many attractions in Iberia, the monuments are exquisite but it’s the feeling of the past that lingers longest in your memory.

After two weeks of adventure and hopping between the cities that have shaped Iberia’s history, you’ll relax while you gaze at the terraced vineyards of the Douro from your hotel terrace. This is a World Heritage wine region, where the grapes are still harvested by hand and the villages stoically maintain their 17th-century style. You’ll have plenty of free time during your stay in the most beautiful of villages to explore at your leisure, with various daily options to go wine tasting at estates nearby. While the wine is exquisite the food is superb, typical Portuguese cuisine from the interior, based on recipes passed down through many generations.

The village of Sao Joao da Pesqueira is a fitting final stop on a Spain and Portugal vacation. Before you reach your final destination, you’ll stop at two exceptional World Heritage Sites that stand directly on the route back to Lisbon. The architecture of Coimbra University is unlike anything you have encountered so far, so novel and new age, even if it was built in the 13th century. Then, the town of Tomar emanates from the walls of the Convent of Christ and is the old city that the Portuguese revere most. Constructed by the Templar Knights it’s a final showpiece of heritage on your vacation. Over the course of your trip, you’ll experience 17 World Heritage Sites, each vastly different from the last.

It takes just over an hour to travel to Lisbon for your international departure. Dependent on your flight time there will be a chance for a final morning stroll in a historic city.