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9-day tour of Spain | World Heritage Sites, Salamanca, Segovia & Toledo

9 Days - 8 Nights

Route

You start in Madrid and cycle via Toledo and Ávila to Salamanca. You then follow a loop via Zamora, Toro and Tordesillas towards Segovia, passing castles, wine villages and historic towns along the way.

Pace

A well-balanced road trip with short drives and fixed bases. You’ll experience a variety of culture, landscapes and wine regions without having to move on every day.

Highlights

From medieval Toledo and the city walls of Ávila to lively Salamanca and the Roman aqueduct of Segovia. Along the way, you’ll taste wines in Toro and discover castles such as Peñafiel.

Accommodation

You’ll stay in central locations, with two nights in Salamanca and Segovia. This allows you to explore each city at your leisure, without rushing.

Profile

For travellers who want to understand Spain through its heritage: cities steeped in history, exceptional cuisine and a landscape that helps tell the story.

Day 1: Departure for Madrid

You’ll fly to Madrid, where your hire car will be waiting for you. Depending on your flight time, you can stop off on the way to visit Chinchón, with its beautiful Plaza Mayor (where bullfights still take place in the summer), and Aranjuez, world-famous for Joaquín Rodrigo’s ‘Concerto’.

Day 2: Toledo

A beautifully situated town on a hill, three-quarters of which is surrounded by the Tagus. El Greco, the painter, lost his heart here and gave free rein to his artistic talent. His masterpiece ‘The Burial of the Count of Orgaz’ can be admired in the Church of Santo Tomé.

Day 3: Ávila-Salamanca

Via the Sierra de Gredos, you’ll drive to Ávila with its impressive medieval city walls. In the historic centre, you can visit the cathedral, the Basilica of San Vicente and the Monastery of Santo Tomás. You’ll then head to Salamanca, where you’ll spend the night at the Palacio de San Esteban.

Day 4: Salamanca

Not to be missed in this charming university town are the Plaza Mayor, the Convento de las Agustinas, La Casa de las Conchas, the cathedral, the university library, the Convento de Las Dueñas and the Convento de San Esteban.

Day 5: Zamora - Toro - Tordesillas

Via the Roman town of Zamora, with its impressive cathedral, you’ll drive to Toro, famous for its fine wines. You’ll then continue your journey to Tordesillas, where the treaty was signed that divided the New World between Spain and Portugal. This is also where Juana la Loca was imprisoned after being declared insane.

Day 6: Valladolid - Medina del Campo - Peñafiel

Choose between a visit to Valladolid, a visit to the impressive Castillo de la Mota, or Peñafiel Castle, the most spectacular due to its location on a narrow ridge.

Day 7: Aranda de Duero - Pedraza - Segovia

Via Aranda de Duero, known for its many underground bodegas, and medieval Pedraza, a particularly charming medieval village with just one entrance gate, you reach Segovia, one of Spain’s most beautiful cities. The city exudes history, with impressive buildings, a Roman viaduct, monasteries, medieval streets and city walls. There is so much to see that you won’t know where to start.

Day 8: Segovia – El Escorial

Fortunately, there is still a day left; take your time exploring this remarkable fortified town further or make a trip to the impressive El Escorial: the castle, abbey and mausoleum of Philip II of Spain.

Day 9: Back home

Your trip is over. You’re flying back home. Unless you’ve got a bit of holiday left, in which case we’d be happy to arrange a few more days in Madrid for you. A lively city full of culture, gastronomy and trendy spots.

Frequently asked questions about the tour of Spanish World Heritage sites
Is a hire car necessary for this tour of thirteen UNESCO World Heritage cities?

Yes. A hire car is essential to get the most out of this tour of Castile. You can travel flexibly between cities such as Toledo, Salamanca and Segovia, and also reach less accessible places such as castles, wine regions and historic villages.

When is the best time to take this tour of Spanish World Heritage sites?

The best time to travel on this tour in Spain is between April and June and September and October. During these months, temperatures are ideal for comfortably exploring UNESCO cities such as Ávila, Salamanca and Segovia.

What makes this tour of World Heritage sites different from other cultural routes in Spain?

This tour focuses on the cultural heart of Spain, with a high concentration of UNESCO World Heritage cities. You’ll combine well-known highlights such as Toledo and Segovia with lesser-visited spots, wine regions and historic castles in Castile.

Why book with Caractère?

Best travel period

Jan
1 - 9°C
36mm
Feb
2 - 12°C
26mm
Mar
4 - 15°C
26mm
Apr
6 - 18°C
46mm
May
9 - 22°C
32mm
Jun
13 - 28°C
29mm
Jul
15 - 31°C
14mm
Aug
15 - 31°C
5mm
Sep
13 - 26°C
40mm
Oct
9 - 21°C
46mm
Nov
5 - 12°C
67mm
Dec
3 - 10°C
35mm
Contact us for your tailor-made trip
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