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Going deep into the undiscovered Extremadura
Visit the most properous 5 Protected designation of origin for wine in Portugal

Highlights of Extremadura

This 14-day roundtrip around Spain’s interior visits medieval towns and natural wonders of Extremadura and its surroundings. The land of the conquistadores, the conquerors who the Americans. It was here where the poor went to the unknown and brought back the wealth from the Americas. This is why now most of the towns are majestic treasures. 


Day 1 | Segovia | Arrival in Segovia

Your holiday starts right in the beautiful city of Segovia, which has been part of the UNESCO World Heritage List for 35 years.
The historic center has plenty of sites to see for those who arrive early. Hop in the center to get the first sights of its castle, palace, and several monasteries. Don´t miss out on the aqueduct that crosses the city.

Day 2 | Segovia | Take a visit to the palace La Granja

Today you have plenty of time to enjoy the center and take a trip to La Granja San Ildefonso, which is about ten kilometers from the city. La Granja is the Spanish version of Versailles in France, it was the king’s summer palace in the 17th century with huge gardens and beautiful halls decorated with tapestries, mirrors, and marble floors. Definitely worth a visit to walk around here.
For those fond of hiking can explore one of its many forests offering many hiking trails that line some of the villages hidden among the pine trees.
In the afternoon you have plenty of time to visit a number of monuments in Segovia that you were unable to visit the day before.

Day 3 | Salamanca | Driving from Segovia to Salamanca via Ávila

You say farewell to Segovia and drive towards Salamanca. Within an hour you make a stop in Ávila, a UNESCO heritage city since 1985. The city has an impressive city wall of 2.5 kilometers long with 87 towers and 9 gates. Part of this wall dates from the 12th century. The varied architecture that the historic center of the city has to offer is a huge influence from its Muslim, Jewish, and Christian past.

After a visit, the ride will take you along the Sierra de Gredos nature park with 15 peaks higher than 2000 meters (6500 feet). The landscape will change into meadows of oak trees where the pigs are eagerly looking for the acorns. It is here where one of the world’s best hams is produced. Make a stop in Guijuelo to visit a ham dryer with a tasting afterward.

From here you travel far towards the historic center of the “golden city” of Salamanca. The city has been a UNESCO World Heritage Site since 1988. It 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.

Day 4 | Salamanca | Explore the center by bike

In the morning a 3-hour bike tour is waiting for you with one of our guides through the center with a guide. He´ll explain to you all about the ins and out´s of the city and its architecture. Furthermore, in the afternoon you can visit the cathedral and the university at your own leisure, where you certainly need a few hours.
You can also enjoy a lovely terrace on one of the many squares in the city. The most spectacular square is Plaza Mayor.
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.

Day 5 | Plasencia | Drive from Salamanca to Plasencia

The day starts with a small detour to make today’s route spectacular. In just over an hour you will arrive in the Sierra de Francia Natural Park. The park is known for the many black slate villages. In addition, the park has been declared a Biosphere Reserve by UNESCO. The park is an excellent place to be surrounded by nature and do not forget to stop at one of the peninsulas in the river that the park has to offer for a spectacular view.

The journey continues along a lake district where you can stop for some photo opportunities. From here the road continues to today’s final destination, Plasencia, a relatively new town, established “only” in the 12th century.

The city has remains of the medieval walls, its towers, and its gates, such as that of the Sun or the shutter of Santa María. In the center, you will also find one of the most representative monumental complexes in the area, formed by the Old Cathedral, of Romanesque design, and the New Cathedral, with Gothic and Renaissance elements.

Day 6 | Plasencia | Visit to Valle de Jerte and Garganta de los Infiernos Natural Park

After breakfast, you head off for a full day drive through the area. The first stop is at the Monastery of Yuste, founded in the 15th century, and was the place the emperor Charles V spent his final months. A little further you will arrive at the castle Jarandilla de la Vera for a photo opportunity of Carlos V´s residence dating back to the 13th century. After about half an hour’s drive, you will arrive at the town of Jerte, known for its valley, Valle de Jerte with several possible hiking routes in la Garganta de los  Infierno. There are routes for any levels, clearly indicated along the way. 

Day 7 | Plasencia - Mérida | Off to the historic Roman city

Just after a short drive, you´ll pass an impressive lake district. After a stop for a cup of coffee and some photo opportunities, you will travel on to the UNESCO city of Cáceres. The center is so well preserved that a large part of the T.V. series Games of Thrones is included here. You can spend at least a couple of hours visiting its many historic buildings.

From here it is another hour south to the 2nd UNESCO city of today, Mérida.

Day 8 - Mérida - Sightseeing in the Roman treasure of Mérida

Today you have plenty of time to visit the UNESCO city of Mérida, known for the largest Roman ruins in Spain. You can easily spend a day exploring the entire center and visiting all the Roman buildings. Look for the amphitheater and Roman bridge still in use.

Day 9 | Mérida - Trujillo | Drive from Mérida to Trujillo

The olive lovers among us can go just half an hour south to visit the olive groves of Almendralejo. A famous region in Spain for its olives. Nearby is also the historic town of Zafra. From here you drive within an hour to the other historic town of Trujillo, known as the hometown of one of Spain´s most famous conquistadors, Pizarro, who conquered Peru. 

Day 10 | Trujillo | Day trip to the Monfragüe National Park

In the morning you drive to the National Park Monfragüe to walk one of the many routes. The shortest route is 8 km. and the longest 23km. We will again provide you with a number of options here. The park is known as a protected bird area and there is a great variety of rivers, gorges, and valleys in this region. You are guaranteed to see the vultures floating through the air. A wonderful day to enjoy nature. From here you will return to  Trujillo where you can see the sites you didn´t get a chance to visit the previous days. 

Day 11 | Trujillo - Oropesa | Drive to Oropesa with a stop in Guadalupe

Your first stop will be the lakes district of Talarrubias for a relaxing morning walk. From here, in just over an hour, you arrive at the UNESCO city of Guadalupe where you will have enough time to visit the beautiful monastery. Today the virgin of this monastery is the national symbol of Mexico, and the most famous virgin in the country, next to María. Fro here on the journey goes to the final destination of today, Oropesa. 

Day 12 | Oropesa - Toledo | Saving the best for last; Toledo

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 13 | Toledo | A visit to the land of Don Quichote

This last day is dedicated to the world-famous book, Don Quixote. At 10:00 am an excursion is waiting for you to visit one of the mills, including a tasting. After the visit of about an hour, continue the day with a visit to a number of picturesque villages which are also described in the book. Every village has dedicated something to the iconic figure. If you drive towards Toledo again, you will make a stop in Consuegra, known as the Spanish Kinderdijk.
In the afternoon you still have enough time to visit the last monuments of Toledo.

Day 14 | Toledo | Home or extension

Today, you´ll head back to the Madrid airport to fly back home after an amazing experience.  

Haven’t had enough and wish to extend your trip or add a few extra stops? Let us know
and we’ll be delighted to tailor-make the continuation of this trip according to your wishes. 

Price information:

Total Price: €1375,- | $ 1675,- per person


  • 13 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)
  • 14-Day car hire with all-risk insurance
  • Insider tips from us from where to go and what to do


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

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