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Highlights 15th Century Spain
The medieval trail through Spain visiting its most iconic sites

Highlights 15th Century Colonial Spain

It was the start of the Golden Ages in the 15th and 16th century; the reign of the Catholic monarchy in Spain. Over the course of this 12- day self-drive itinerary, you’ll begin in Spain´s capital of Madrid and end in Málaga at the Mediterranean, admiringly  tracing the very paths
of those who changed the course of history ages ago.  

The medieval trail through the interior of Spain visits iconic cities that dominated, where the Catholic monarch reigned and Christopher Columbus and Pizarro were prominent figures. Pass through the Extramadura region and visit the birthplaces of the well-known explorers, Hernán Cortés and Francisco Pizarro. 

Going farther south, you’ll visit Seville – the place where Columbus sailed off from on his venture to discover the Americas. Your trip will continue the former Islamic capitals of Al-Andalus: Córdoba and Granada, and finish off in the vibrant and sunny city of Málaga.


Map itinerary

Day 1 | Arrival to Madrid | Orientation Madrid

Welcome to Madrid! A private taxi awaits you at the airport and accompanies you to the hotel.

For those arriving early, you’ll have an option to kick start the tour by diving right in. Walk about the center and grab your first impressions of the grand streets and bright architecture. You’ll soon discover a wonderful assortment of elegant boulevards, illustrious museums, royal palaces, manicured parks, and trendy eateries.

Its center is a collection of diverse barrios which each boast a distinct charm, and lay claim to architectural wonders including the 17th century Plaza Mayor and vast Royal Palace. 

We also recommend a visit to Gran Via, the city’s most famous shopping boulevard, and Puerta del Sol, the so-called ‘Heart of Spain’ and home to the famous Bear and Strawberry Tree statue, which has become a symbol of the city. 
There’s something for everybody here!

Day 2 | Madrid | Colonial Madrid or an excursion to historic Toledo

On your second day in the Spanish capital, you´ll really begin to soak up the culture with many diverse neighborhoods to visit, sights to see, and local products to purchase. Have a picnic in the gardens of the huge central park – Retiro.

Art lovers will rejoice in the city’s ‘Golden Triangle of Art’ comprising the art museums: Museo del Prado, Museo Thyssen-Bornemisza, and Museo Reina Sofía,  which display works from many of the world’s artistic heavyweights.

Fashionistas looking for another retail hit should head to the barrio of Salamanca, home to glamorous avenues and the famed ‘Golden Mile’ of Calle Serrano with its upscale boutiques and stores of famous fashion houses. 

Another option is to visit nearby Toledo. A fortified city once dominated yet blended peacefully by three cultures simultaneously: the Christians, the Arabs, and the Jewish, has infused it with a highly unique historical and architectural offering. Located atop a gorge above the Tagus river, this is a must for culture lovers who will revel in exploring the vaulted mosques, Sephardic synagogues, and Gothic cathedrals, as well as the artworks of El Greco with whom the city is synonymous. 

Day 3 | Madrid – Ávila – Salamanca | From the capital to Salamanca

Begin the 2.5-hour journey this morning towards Salamanca. Jump at the opportunity of a warranted pit stop in the fortified town of Avila to see its spectacular wall and watchtowers. Walk through the medieval center, and enjoy lunch in the main square while taking in the surroundings.

One hours’ drive later, you may peruse the city of Salamanca. Don´t miss out on the stories and secrets behind the historic monuments and buildings in the center.

Day 4 | Salamanca | Walk through the UNESCO´s historic city centre

Salamanca is known as the golden city, for the incomparable color of its stone of Villamayor and whose Plaza Mayor is considered the most beautiful in Spain.
Look centuries back to the time of academic richness and adventure, crossing into the very same structures where history was made. Regularly visited by Columbus, one of the oldest Universities demands your attention. Spot the frog, as for centuries it has given students success in their studies.

Let wonder itself lead you through the charm this city has to offer. The town center, lush gardens, pre-17th century buildings, hidden courtyards, and everything falling between convents to palaces, command your attention and your photography skills. Find the golden stone of Salamanca by allowing the bustling Rua, and Compañía Street brings you to the Plaza Mayor.

Nearby you can make a half-day morning excursion to the historic villages in the Sierra de Francia, a mountain range located at the southern end of Salamanca Province. Today the region is sparsely inhabited and it’s few towns have great cultural value. Stop at the old town of Ciudad Rodrigo, known for its 12th-century city walls and Gothic and Romanesque architecture. Peek into how life has stood still here and glimpse at how people lived during this epic time that spanned centuries.

Day 5 | Salamanca - Guijuelo – Cáceres | From gastronomic ham to the UNESCO heritage city of Caceres

Today you’re heading to Cáceres in the Extremadura region, with a short stop in Guijuelo, a short 30 minute drive through the acorn tree fields and home of the famous Iberian pigs, both spotted along the way. Guijuelo is known for producing one of the best hams in the world. Here you may visit one of the natural ham drying cellars.

Next, the option to also take in the town of Trujillo, which claims its fame as the birthplace of Peru´s conqueror, Pizarro.
Cáceres was founded by the ancient Romans and subsequently by many different cultures. Film addicts may recognize this UNESCO heritage town, which recently and proudly displayed its medieval characteristics in the Game of Thrones.

Day 6 | Cáceres – Mérida – Seville | Off to Seville and the Roman site of Merida

Take an early morning walk through Cáceres over the ancient cobblestoned streets and witness the sun slowly illuminate the historical buildings in the center. Glance upon the fortified houses, palaces, 12th-century Moorish walls, and 30 towers this small town places in front of you.
We urge you to stop in the historic city of Merida, home to the largest quantity of Roman ruins remaining in Spain. Dating from 1st century B.C, there are three marvels here to have the privilege of seeing. Teatro Romano, amazingly still in use today; the ancient bridge of Puente Romano, and the Alcazaba – a 9th-century Islamic fortress built onto the pre-existing Roman walls which still exist today.

Continue onward. Eyes open to not miss the cathedral towering above the city center, a grand welcome as you approach the city of Seville.

Day 7 | Seville | Walk in the footprints of Columbus

Even the likes of Christopher Columbus were not immune to Seville’s charms, who used its (now modest-seeming) port as the gateway to the ‘New World’, which led to a boom in its economic, social and cultural growth. Such was his connection to the city that his tomb is located in its colossal cathedral, which still stands as the largest Gothic cathedral in the world. Occupying the site of an Islamic mosque, the vast structure retains its minaret, now converted into Seville’s emblematic Giralda (bell tower), and idyllic orange tree courtyard. 

This marriage of Moorish and Christian culture can also be seen in the neighboring Real Alcazar, the oldest royal palace in Europe whose geometric mosaics, ornate latticework, water fountains, and recessed gardens stand as one of the most outstanding examples of Mudejar art in existence. Seville’s vast Plaza de España is further evidence of its architectural genius.

Day 8 | Seville | Seville in combination with Europe´s biggest bird migration National Park

Today you have the option to either explore more of Seville and visit Triana and Macarena, the cities two most traditional neighbors. Triana a microcosm of artistic energy with an excellent market, traditional ceramic heritage, strong flamenco connection, and long gypsy and bullfighting history, while Macarena is known for its hip, creative vibe, the Macarena is home to one-off shops selling vintage clothes and books, or the Mercado de la Feria market hall with stalls serving paella and croquettes. Nearby, tapas bars dish up seafood and empanadas,  and a number of snugs, hidden bars keep the area buzzing until the small hours. 

If you feel the urge to escape the city, we suggest going to either the Doñana National Park known for its 400.000 migration birds or visit Jerez de la Frontera, a paradise for the sherry lovers. Below we have two options for you, bookable via us, or undertake it on your own.

Day 9 | Seville – Granada | From Catholic Seville to the Arab Granada

In under three hours you drive through the ancient old olive fields planted by the Romans and Moors to the city of Granada, another exceptionally beautiful city whose status as the last Moorish kingdom is deeply woven into the fabric of the city. You can make a stop in historic cities such as Carmona or Antequera. 

Today, we recommend exploring the city on foot to best appreciate its dramatic setting in the foothills of Sierra Nevada. Enjoy its gastronomy scene, whose large tapas portions have earned it a place in the hearts of food lovers.

This legacy is no more evident than in the Alhambra, a spectacular Islamic palace atop a hilltop which you’ll have the opportunity to visit tomorrow.

Day 10 | Granada | Unwind in the Jewel of the Alhambra

Be sure to leave at least four hours free today to explore the jewel in Granada’s crown the Alhambra – whose sprawling complex and unabashed grandeur truly justifies its worldwide reputation. Its Renaissance residential palaces, opulent frescoes, decorated columns, and open courtyards are a lasting monument to the pivotal part the city played in Iberian history, while its gardens are an oasis of calm and serenity. 

In the afternoon, we suggest venturing into the Albaicín neighborhood, the old Arab Quarter which has retained a strong sense of identity and wonderfully imperial energy. End the day with a visit to the Sacromonte neighborhood, the thriving folkloric gypsy quarter which lures visitors to its hillside location for flamenco music and dancing after dark. 

Day 11 | Granada – Malaga | Final track to Malaga, on the Mediterranean coast

This morning you’ll drive the final 150 kilometers along the Mediterranean Sea, arriving in Malaga in time for a lunch of fresh Mediterranean fish and cold local beer. Revamped and revitalized, this once overlooked city has become an epicenter of culture and art, laying claim to world-class galleries including the Parisian-offshoot Pompidou Centre and the Picasso Museum, in homage to its most famous offspring. Its old town is a nod to its rich history and cultural heritage, whose network of cobbled streets hide a treasure trove of historic buildings and picturesque plazas. You’ll also find a 1st-century Roman amphitheater, a beautifully preserved Moorish Alcazaba fortress, and the 11th century Castle of Gibralfaro, whose position atop 130 meters awards it some of the greatest views of the city. For those who have met their cultural quota, this multifaceted city also boasts wonderful beaches, excellent Andalusian cuisine, and an abundance of shopping opportunities. 

Day 12 | Malaga – Home | Home or extension?

You have the option to fly back home directly from Malaga or to take a train to Madrid to catch your outbound flight. We´ll arrange a hotel pick-up for you by private taxi to the airport.

Should you wish to extend the trip further and experience more of Spain’s gems, or adjust the itinerary we would be delighted to tailor this to your wishes. 


Total Price: From € 895,- / $ 1075,- per person


  • 11 Nights in a 2- to 3-star hotel including breakfast (let us know if you prefer an upgrade to a 4- or 5-star hotel)
  • Car hire for 9 days including all-risk insurance
  • Pick-up and drop off from and to the airport
  • Insider tips from us from where to go and what to do


  • Plane tickets (we can arrange these for you if you wish)
  • Insurance
  • All other food and drinks not mentioned in the description
  • Tips and all other private expense0