From Nativics we have prepared this medieval route by car for 5 days through the cities of Toledo, Ávila, Salamanca and Segovia. All of them were declared World Heritage Sites by UNESCO. It includes 4 nights of accommodation in the two Castillas with one hotel night in each city for you to enjoy day and night and the best itinerary with suggestions and practical advice.

5 Days / 4 Nights
per person

Are you interested?

Make your search and ensure the best price.

Experience Details

Travel guide of 5-day medieval route through Toledo, Ávila, Salamanca and Segovia

Day 1:

Toledo, the city of three cultures

We begin our route through the medieval city of Toledo, one of the most visited cities in Spain, which, although small, has a lot of history and much to discover. The greatness of its beauty is that, within its walls, three cultures coexisted for decades in relative peace: Muslims, Jews and Christians. Each one of them contributed a part to the personality of the city, which is still preserved today and that we are going to discover in this itinerary. Let's start the visit!

First of all, Toledo has several gates around the walls that served as entrance and exit: Puerta de Alfonso VI, Puerta del Sol, Puerta del Cambrón and the most famous, the Puerta de la Bisagra. If you have the option, since it will depend on the direction you are coming from, it is a good way to enter the city in a big way and, if not, you can go through one of them at any other time. 

That said, the best option to start the route through the medieval old town, a World Heritage Site, is to do it in the Plaza de Zocodover, a historic square surrounded by Castilian buildings, bakeries and stores. This almost triangular main square has samples of Arab architecture since at that time it was the city's souk. Hence its name, which means "market of the beasts" in Arabic. But what makes this square special is the building that stands in it: the Alcázar of Toledo. This fortress is located at the highest point of the city and has had different inhabitants throughout history, from the Roman palace in the third century to the palace of Charles I, among others, it was of great strategic value. The most beautiful of this building is on the outside, we recommend that you surround it to see all its facades. If you want to see the views of the city, you can go up to the cafeteria on the top floor of the Library of Castilla La Mancha. The entrance is free. Inside the Alcazar is the Army Museum, the entrance is cheap and you buy it there but, from our point of view, with only one day of the visit, you might want to give it a miss. 

When you leave the Alcazar, head towards the Catedral Primada de Toledo, located in the same square as the Town Hall. The good thing about this city is that everything is within walking distance. Of course, there are slopes everywhere... To enter the cathedral a paid entrance is required. It is open from Monday to Saturday from 10 am to 6:30 pm, however, on Sundays, it is only open during the afternoon, from 2 pm to 6:30 pm. This beautiful large cathedral of Gothic style with French influence began to be built in 1226 on the foundations of the Visigothic cathedral of the sixth century, which was also used as a mosque. Composed of five naves, it is 120 meters long and 60 meters wide and has 88 columns and 72 vaults. As soon as you arrive you will be impressed by the beauty of its architecture. If you walk around the building, you will discover its three magnificent facades: the main facade, the Clock Gate and the Lions Gate. Inside is the Sacristía Mayor, of relevant importance because it is where the famous painting of "El Expolio", by El Greco, a famous painter who lived in Toledo, is exhibited. The chapels, the choir and its 18-ton bell, popularly known as "La Gorda" and for being the largest in Spain, are other outstanding elements of this building.  

Once you have visited the Primate Cathedral of Toledo, it is time to visit the Church of Santo Tomé, more modest but of great value for what it houses inside, the famous painting by El Greco called "The Burial of the Count of Orgaz". Leaving the parish, if you are a lover of El Greco's paintings, you can go to the Museum of El Greco, but it is not an essential visit 

After the cathedral and the church of Santo Tomé, it is time to enter the Jewish quarter. There are several synagogues but we will focus on the Synagogue of Santa Maria la Blanca, the most beautiful monument of the Jewish quarter of Toledo and the favorite of those who visit it. This Mudejar-style synagogue stands out for its ornamental interior that contrasts with the austere exterior of the building. In it, we find white walls, horseshoe arches and 32 octagonal pillars covered with cement and lime that stand out for their capitals decorated with ribbons, pine cones and scrolls. Undoubtedly, the Moorish style of this ancient Major Synagogue is what is most striking and what makes it so special and essential in your visit to Toledo.

Continuing with our itinerary, the next monument to discover is the Monastery of San Juan de Los Reyes. This Elizabethan-style monastery with Mudejar influence is what makes it unique along with its history since it was Isabella the Catholic who had it built. She was so impressed by the city that she thought it would be a good place to bury her mortal remains and those of her husband, Ferdinand of Aragon. As is well known, in the end, this was not the case, since the Catholic Monarchs decided to stay in Granada during their last conquest and dedicate this temple to Saint John the Baptist, to whom Isabella of Castile was devoted. Even so, with the initial intention, you can get an idea of the dedication with which this monument was built. Do not miss its Elizabethan facade and its cloister!

And to finish with the walk through the three cultures, you can not miss the Mosque of Cristo de la Luz. It closes, like most monuments in Toledo, at 17:45h, so try to be there at least 30 minutes before. Its architectural and decorative elements are a miniature sample of the Mosque of Cordoba, so surely this jewel of Islamic art and the legends it hides will not leave you indifferent. 

Once you leave the Cristo de la Luz, you have two options: continue getting lost in the streets, stop in some of its stores, buy some sweets or go to the Mirador del Valle, from where you can see spectacular panoramic views of the city. To get to this viewpoint will take you 10 minutes if you do it by car or 40 minutes if you walk. If you arrive in time to see the sunset, it will be the perfect end to the day, the icing on the cake! 

Now it's time to find a place to have dinner, rest a bit and be dazzled by the city of Toledo at night, a real wonder!

What will you see today?

Day 2:

Ávila, beyond the wall

First thing in the morning, it's time to continue with our medieval route leaving Castilla-La Mancha behind to move to Castilla y León where our first stop will be Ávila, just under 2 hours by car. This city, World Cultural Heritage, is known for its magnificent wall located in a beautiful part of the city, on our first visit, but the truth is that it hides many more treasures that you will discover on this day. 

First thing in the morning, it's time to continue our medieval route leaving Castilla-La Mancha behind to move on to Castilla y Leon where our first stop will be Avila, just under 2 hours by car. This city, a World Cultural Heritage, is known for its magnificent wall located in a beautiful place of the town, which is our first stop, but, the truth is that Avila hides many more treasures that you will discover over the day. 

Today begins, of course, with a visit to the Wall of Avila, the icon of the city. We will access it from the Puerta del Alcázar as it is the most emblematic, although it is also possible to do it from the Casa de las Carnicerías and the Puerta del Puente. This impressive medieval wall from the 11th century has a perimeter of 2,516 meters, 87 towers, 9 access gates, including the Gate of San Vicente and the Gate of the Alcazar, 2 gatekeepers and 2,500 merlons, and boasts of being the best-preserved walled enclosure in Spain. Undoubtedly, it is a genuine movie wall ... But best of all, you can walk along much of its layout and stroll along the walls. From there you will be able to see the intense green color under its feet and how beautiful the city is. 

Leaving the wall, if you go down the street of the Old Cross, you will reach the Cathedral of Christ the Savior or Cathedral of Avila. While it is true that its facade is not very striking, but rather austere, the interior is worth it. Of Romanesque style and with more than 300 years of construction, you can appreciate elements of different influences such as the Gothic, observable in its impressive High Altarpiece, and the Renaissance in which stands out the laborious Choir, worked in detail on walnut wood, and the Transcoro, pilasters decorated with high reliefs depicting The Presentation in the Temple, The Adoration of the Kings and The Slaughter of the Innocents. Another part of the cathedral you can not miss is the Girola, not only because it is the oldest element of the temple and the most architecturally important, but because it is a real beauty. Of course, do not leave without taking a tour of the cloister. 

 From the Cathedral we go to the Basilica of San Vicente, located outside the walls, passing through the Puerta de San Vicente. It will take us no more than a five-minute walk to get there. This is the advantage of walled cities, which have everything just a few steps away. Arriving at the basilica, you will see that its facade is a different color from the rest, perhaps a little orange. Also in Romanesque style, the work on this parish church, still in use with worship celebrations, began in the year 1120. According to tradition, it was here that St. Vincent was martyred and buried and, as a result, the church was named Basilica of St. Vincent. After leaving the basilica, head towards the Plaza del Mercado Chico along Calle López Núñez. On the way, you will pass the Palacio de Monjaraz and the City Hall, next to the square. In this area of the old city, you will find a variety of restaurants where you can eat and rest.  

In the afternoon, you can take the opportunity to visit the Convent and birthplace of Santa Teresa de Jesus. This Carmelite Baroque church was built over the house where Teresa de Cepeda y Ahumado was born, now the chapel of Santa Teresa. Below it is the Teresian museum, in the large crypt of burials. The façade is divided into three parts in which the image of the Saint in marble and the coats of arms of the Cepeda and Ahumada families stand out. In the same square where the Church of Santa Teresa is located, you will also find the Hall of Relics and a small souvenir shop in case you want to take some souvenirs home.

To end the day, nothing better than enjoying the sunset at the viewpoint of Avila, the shrine of the four poles. Walking you will get there in about 15 minutes, passing by the Roman Bridge of Avila that crosses the Adaja River. After this, you just have to enjoy the beautiful night of Avila and, why not, enjoy a good steak. 

What will you see today?

Day 3:

Salamanca, the university city World Heritage Site

Salamanca is another city in Castilla León that boasts of being a World Heritage Site. Its historic center is easily explored on foot and it contains the most representative monuments of Salamanca, a university city full of culture, art and legends. To get there by car from Ávila will take just over an hour. 

As soon as you arrive in Salamanca, there is no better way than to start this tour through the Plaza Mayor, full of life, bars and restaurants until you reach the cathedral complex where the New Cathedral and the Old Cathedral, one attached to the other. If you want to enter them, tickets are purchased at the temple itself or on its website. Although we already anticipate that its famous facade is the biggest attraction and you can see children and adults playing to find some of the elements it hides. On the facade of the New Cathedral, you should find an astronaut and a dragon with an ice cream. If you go with children, this will surely keep them entertained for a good time... 

If you feel like it, you can also climb the medieval tower of the cathedral, the Ieronimus. From there you can walk through the terraces that overlook the interior of the temple and see the views of the city. Our recommendation is that, if you want to save time and effort, choose between this tower or the Clerecía tower, another stop on our route, also with views of the city.

From the cathedral, we will continue to the University of Salamanca, a historic building over 800 years old and an academic benchmark. This facade is also the claim of many visitors who stay in front of it until they find the little animal that is hidden: a small frog.

Once you find the famous university frog, go to the Casa de las Conchas. The name comes from the fact that its façade is full of shells. If you want to see its inner courtyard and its library, admission is free although, without a doubt, what is most striking is its exterior. Right in front of the Casa de las Conchas, is located la Clerecía, as the Royal College of the Holy Spirit of the Society of Jesus is called. The part that we are going to visit will be its towers rising through the Scala Coeli, a stairway to heaven. From above you can see spectacular views of the entire city. In the same square, you will find the Pontifical Universitywhich you will pass in front of. 

Going down Calle Meléndez, you will reach the Puente Romano. Stroll over its walls while you contemplate the views of Salamanca and cross the Tormes River, then return over the same bridge and walk to Casa Lis, a modernist-style mansion with stained glass windows most beautiful colours. Its façade is fascinating and its interior houses the Art Nouveau Art Déco Museum. On this one-day route, it is advisable that, if you are not a lover of this artistic style, you avoid entering as it will take time away from other more relevant monuments.

Continuing with the itinerary, yes If you want to walk through the Huerto de Calixto y Melibea, you should do it before sunset since it closes after sunset. This landscaped space has beautiful views of the Tormes River and the Cathedral. There you will find a statue of the character of Fernando de Rojas, the old Celestina. This is because it is believed that it was in this garden that the writer set the scene of the meeting between the protagonists, Calixto and Melibea. 

To end the day, nothing better than visiting the Palace of Salina or Fonseca. Admission is free and closing time is at 8pm. Public access is only to the patio, the most interesting place for its Dantesque columns in which different faces appear with expressions of horror. This palace was also salt-watertight, hence the popular name, and is currently the headquarters of the Provincial Council of Salamanca.

In the evening enjoy a good dinner in one of its restaurants and the lively atmosphere of its university streets. From the other side of the Roman bridge, there are stunning views of the illuminated city. If you feel like going for a walk after dinner, it is a most romantic place.

What will you see today?

Day 4:

Segovia: from the Aqueduct to the Alcázar

The route of a day in Segovia begins at the very Aqueduct of Segovia, the most emblematic monument of the city that has been standing since Roman times and is part of the Segovian landscape. It is certainly worth appreciating that after so many centuries we can enjoy this construction of pure engineering. Those Romans knew what they were doing...

After taking a picture with the famous aqueduct, we will continue to the Calle Real that connects the aqueduct with the Plaza Mayor. This street is the most commercial street in Segovia, so as you walk along you will come across local stores and international chains, souvenirs and stores selling typical products of the area. Although it is known as Calle Real, it is made up of three streets: Calle Cervantes, Calle Juan Bravo and Calle Isabel la Católica. In this popular street is the Mirador de la Canaleja and the Casa de Los Picos, both places of obligatory stop ... From this viewpoint, you can contemplate the fabulous views of the mountain of the Mujer Muerta and the Barrio de San Millán, so it is recommended that you spend a few minutes enjoying the scenery. Continuing on the same Calle Real, you will come across the Casa de Los Picos. What makes this building so special is the dozens of diamond-shaped spikes protruding from the facade, all of them arranged neatly in an orderly fashion, which gives it an unusual and very beautiful appearance.

After seeing the facade we will continue along the same street but taking the section of Juan Bravo until we reach the Plaza de Medina del Campo, also known as Plaza de las Sirenas because of the sculptures that refer to this mythological figure. Of course, do not imagine the sirens sweetened fairy tale, with big manes and slender bodies ... They are rather a mixture between the body of a lion and a woman with crown and veil, more similar to a sphinx. In this square also stands the statue of Juan Bravo, behind it, there are small stairs leading to the Plazuela de San Martin, where the beautiful Tower of Lozoya and the Church of San Martin are located. This Romanesque church stands out for its exterior with its imposing bell tower. If you want to visit it, the access is on the left side of the temple but it is not essential.

Once you have admired the tower and the church of San Martin, going up the Plaza de Medina del Campo, you will reach the Plaza del Corpus, in the Jewish quarter or Jewish quarter. There you will find the current Catholic church of Corpus Christi, which gives its name to the square and which was formerly the Main Synagogue. If you dare to enter, you will appreciate a certain resemblance to the synagogue of Toledo for its white interior. Once you have discovered the Jewish quarter, if you continue along San Frutos Street, you will arrive at the mythical Plaza Mayor, the nerve center of the city where you will find the City Hall of Segovia, the Juan Bravo theater with its peculiar pink facade and the statue of the writer Antonio Machado, who lived and taught in the city as well as proclaiming, on the same balcony of the City Hall, what was the Second Republic of Spain. Well, at this point, you are in the perfect place to stop for lunch before continuing with this itinerary. Almost in all the restaurants, you can eat the typical roast suckling pig that is so soft that you can cut it with a plate. A spectacle for the senses that, if you are a meat lover, you cannot miss. 

In the afternoon, just after lunch, it's time to visit the Cathedral of Segovia, one of the late Gothic cathedrals in Europe that stands in the Plaza Mayor. Although its official name is the Cathedral of Our Lady of the Assumption and San Fruto, it is also known as the Lady of Cathedrals for its great beauty and elegance. A monument not to be missed. Just walking in a straight line, about 10 minutes away, you will come across the majestic Alcazar of Segovia. An impressive fairy-tale castle that rises above the entire city creating an idyllic setting. If you want to enter the fortress, remember to arrive before 6 pm, the closing time. If you follow this itinerary, you won't have the slightest problem arriving on time. 

there is nothing better than to end the day at the Mirador de la Pradera de San Marcos, from where you will have the best views of the Alcázar of Segovia. To get there it will only take you about 15 minutes walking from the Alcazar. If you are looking for places to dine, around the Plaza Mayor you will find a wide range of bars and restaurants. Enjoy the last night of your vacation in Segovia.

What will you see today?

Day 5:

Farewell to Segovia and return home

After waking up in the beautiful city of Segovia, it's time to say goodbye to this medieval route through the World Heritage cities of Castilla la Mancha and Castilla León and return home. 

 at the end of this day, you can spend your free time doing some shopping, eating or having a drink on a terrace, strolling through its streets or, if you have come by car, go to the San Ildefonso Farm for just about 20 minutes from the city. Its gardens are spectacular and it is known as “the Spanish Versailles”. well worth a visit before returning home.

We hope you have enjoyed this route by car and that, if you have been left wanting more, book some of our complete weekends week in Toledo, Ávila, Salamanca and Segovia. 

Contact an expert

If you have any questions about this experience, if you want more details or if you want to customize your trip, don't wait any longer! Contact us and we will help you tailor your trip.

Contact us if you need to add flights, rental cars, transfers or events to your trip. We will solve all your doubts and we will help you finalize your reservation.