Legacy of Old-World Iberia: Two-Week Historical Tour From Madrid to Lisbon

Spain almost stumbled upon its wealth, the unified nation less than a century old when Columbus spotted the land of the Americas. Within another century, Spain was the wealthiest nation on the planet with the capital city of Madrid. After a chauffeured airport transfer and some relaxed time at the hotel, you will be introduced to the city by connecting the two vast memoirs from the glory years. First, the largest of all Europe’s royal palaces with so many glittering archways and grand rooms doused in murals.  From there, enjoy the Plaza Mayor, the centerpiece of Madrid’s cultural life with so many terraces where you can sip a glass of wine as the facade reflects red in the fading sun. Walking between them, you will get a sense of how the historic center of Madrid remains the vibrant heart of the city, some 500 years on. Looking for the best Spain travel ideas? Consider browsing our Spain travel reviews page.

The Golden Age does not refer to Spain’s immense wealth, but to the artistic movement that thrived during a similar time. It’s a movement of thick oily swirls on wall-sized canvases, regal battles playing out on a monumental scale, towering portraits that peculiarly hint at sarcasm. These are all found in the Prado Museum, which rivals the Louvre as Europe’s most important historical art gallery as it contains the most complete collection of the old Spanish masters. Stop for a classic Madrid lunch with your guide and then spend the afternoon at the Renia Sophia, home of Spain’s surreal generation of artists with galleries filled with the works of Dali and his contemporaries that will lead you to Picasso’s Guernica. Exploring both museums also gives you a chance to see the surrounding neighborhoods, some of the grandest in Madrid.

On the short high-speed train journey to Avila, you will get a glimpse of the golden plains that are synonymous with Central Spain. Soon you will come upon the glistening white of the Avila city walls, their turrets epitomizing the battles and quarrels that have scarred these plains over the centuries. Avila is a tiny old city, perfectly preserved in the early part of the second millennium, the cobbled streets, and leaning houses from the 11th and 12th centuries. After lunch, you will return to Madrid for an afternoon at leisure, before an iconic tapas crawl allows you to taste the different regions of Spain. Each of the taverns you visit has a chef from a distinct region so that you can sample bites from Andalusia, Murcia, Galicia, and Catalonia.

Outside of Rome, it is very rare to find Roman relics that remain an integral part of a city. But the two-tiered aqueduct running through the heart of Segovia would look like an architectural marvel if it was built in the 20th century. The faded red brick shows how it comes from 2,000 years before, an astonishing achievement that still forms the centerpiece of Segovia today.  A new high-speed train line has cut travel time to just 30 minutes between Madrid and Segovia, and you can arrive and spend your morning on a tour of the historical landmarks. The afternoon and evening are at your leisure for a chance to fully absorb the ambiance of the Roman legacy, many of the lanes maintaining their 2,000-year-old grandeur.

Continue by high-speed AVE train, whizzing across the scorched plains of Castilla y Leon to a city that has defined glamour for more than eight centuries. Salamanca’s large old center has always been pedestrianized, packed with aristocratic mansions and palaces, monasteries and universities, cathedrals and plazas. These buildings followed the architectural tastes of their era, and the facades bring you on a 600-year journey from Romanesque to Renaissance, then Gothic ghouls to the Baroque elegance of the 18th-century Plaza Mayor. The beauty of these contrasting designs is held together by the harmony of the building material, everything in Salamanca’s old center is crafted from a unique red-gold sandstone. A guided tour will introduce you to the major sights, and then the evening light is the perfect time to explore at leisure and appreciate the allure of the city.

Salamanca deserves time as it is such an elegant and evocative city that can only be explored on foot. After a morning at leisure, you can spend the afternoon at a nearby bodega for a traditional lunch from the plains accompanied by a tasting of wines from the region. Then a private evening Salamanca tour pays particular attention to the sculpted figures that line the entranceways of buildings. Rare and remarkable, these strange stone carvings also transcend the architectural styles. An allegory of vice and virtue lines the university entrance, astronauts, and goblins are part of the new cathedral facade, shells and dolphins mark Casa de las Conchas, and you will enjoy a deeper immersion in the contrasts of styles by checking out how the figures were carved. The tour ends at a wine terrace, overlooked by a 15th-century monastery, where the wines of Ribera del Duero and Toro regions can be tasted by the glass.

Today you will travel by road for a guided journey into Spain’s most untouched old-world province: Extremadura. Villages cling to the hilltops while castle remains are scattered amongst the fields and the oak forests are where black Iberian pigs roam free. Stop at the Guadalupe Monastery, its story etched in legend and battle, its facade a paradox of grandeur and asceticism. Sample a classic lunch of local hams and cheeses in a local village, Extremadura’s produce regarded as the best in the country by the Spanish themselves. Continue from there to Trujillo, one of Spain’s most romantic cities, the main plaza illuminated by wrought-iron lanterns into the evening.

Follow the winding streets, and you can explore two contrasting centuries. Part of Trujillo reminisces of the 13th century and the Reconquest, while the other is from the 16th-century and the conquistadors, who pumped money into the city that built the fabulous mansions. Check out the statues of those that conquered, including those who colonized Peru along with their Incan wives. Then lounge on a square from the past, Trujillo the epitome of Spain’s languorous atmosphere, so relaxing and resplendent as the sun fades from the sky.

Now you will head into Caceres, the most untouched of all the old cities, partially left in an evocative state of ruin. After the short transfer by road, the afternoon will provide an orientation to the city that will follow the storyline from Alfonso IX to free trade prosperity through the 13th and 14th centuries. Caceres is an old-world version of Monaco or another European municipality tax haven, where the merchants and aristocracy compete to build the grandest homes and palaces. This was mostly before Spain’s wealthiest years, and a large part of the grandeur has been retained in the Caceres of the 21st century, as there are virtually no other cities with significant remains from the 13th and 14th centuries.

After breakfast, you will continue to discover the wonders of Caceres with the day at your leisure. Wealth was laid upon wealth until the 16th century when the decline of the local economy coincided with the decline of the Renaissance architectural style. The result is a wonderfully intimate city that is almost exclusively from the Renaissance era, the mansions dominated by ornamental facades that showcased the wealth of a particular family. You have the chance to forget about everything and soak up the ambiance of a time that has long since past. Walk along the narrow cobblestone paths, visit the stone walls wrapping around the palace, and soak in the medieval ambiance in cafes or from the top of Torre de Bujaco.

Wander over the suspension bridge, beneath the Roman city entrance, past the remains of the Arab fortress to a Roman theater that has been exceptionally preserved. Other Roman remains dot this city founded by Augustus for a great insight into how far the Empire spread across the Iberian Peninsula. You will find a chapel from the third century, a temple of fluted columns, and then an aqueduct of towering granite and brick arches. This day in Merida continues through the centuries, the city is home to some of the best Visigothic art in the country plus one of Spain’s oldest Moorish buildings, completing a story that is firmly based in the first millennium AD. Like all the destinations on this luxury tour, there are many elegant al fresco restaurants for your evening dining.

It’s a scenic transfer to Lisbon with most of the journey spent in Portugal, crossing the rolling hills of the country’s interior. While Madrid is charming and slow-paced, Lisbon is full of energy and vitality. Take some time to relax at the hotel before your introduction to the city, taking the number 28 tram across the seven hills, from the castle to the cathedral via the tightly-packed central neighborhoods. Spend the rest of the evening dining at TimeOut Lisbon, a marketplace that brings together the city’s best restaurants and chefs. Your guide will advise you about the two Michelin-starred chefs that have stalls at the market and serve up modern takes on traditional Portuguese cuisine.

In a city of contrasts, there are two neighborhoods that best showcase the extremes. Monumental towers and mansions fill riverside Belem, some of them leaning out across the water for a show of wealth and grandeur and insight into the regal side of both Lisbon and Portugal. From these wide tree-lined boulevards you can travel to Barrio Alto, where cramped old streets ascend and descend what has traditionally been a very working-class neighborhood. Revitalized in recent decades, this area is now packed with vintage stores, cute cafés, vibrant bars, and an atmosphere that lingers long in the memory. The evening is free for your enjoyment, and you will find many excellent places to dine across Lisbon.

Just outside of Lisbon and hiding in the forested hills lies the royal palace of Sintra. This long-time home of the Portuguese Royal Family was first mentioned by explorers in the eighth century, but nobody is quite sure when the Arabic-style palace was built. Peculiar circular chimneys dominate from afar to create this sense of a fairytale in the trees. A cobbled royal village is explored nearby before your tour continues through the large Sintra park, where other regal residences await discovery. Along the way, you will find blissful beaches, strange caves, and natural chimneys, plus a selection of postcard panoramas that complete the impression of Sintra. Return to Lisbon, and this last evening is at your leisure with your guide providing dining recommendations.

Depart the Iberian Peninsula from Lisbon’s international airport, after a relaxed morning in the Portuguese capital.