Segovia's Alcázar on its rock at dawn, above the trees of the river valley

Sample journey · 8–10 days

Old Castile, from the Prado to the golden stone of Salamanca

Madrid, Toledo, Segovia, Ávila, Salamanca & the Sierra de Francia

Photo: Isabel Déniz / Unsplash

Illustrative journey ideas — not bookable packages. No prices, dates or accommodation are implied.

The Castilian plateau is the Spain that gave the world its language, its kings and much of the history we learn at school. Its towns stand on rocks and hills as if each were a fortress of its own: Toledo above a loop of the Tagus, Segovia with its Alcázar like the prow of a ship, Ávila behind unbroken medieval walls. And Salamanca, one of Europe's oldest university towns, is built from a sandstone that glows gold in the evening sun.

The journey begins in Madrid, with its museums, the Retiro and late dinners, and travels north-west until it reaches the Sierra de Francia near the Portuguese border: stone villages with timber beams, chestnut woods and a sanctuary on a summit. The first part is by train, which reaches Toledo or Segovia from the capital in half an hour; the second is by car. It suits couples and curious travellers, especially those visiting Spain for the first time who want to understand where it comes from, and each town can be shaped around your interests, from painting to the kitchen.

The route

The journey

Madrid
Toledo
Segovia
Ávila
Salamanca
La Alberca & the Sierra de Francia
Madrid

01Days 1–4 · Madrid
Paintings, a park and late dinners
Three nights in a capital that lives late: lunch starts around two, and dinner no earlier than nine. A morning at the Prado with a guide who helps you find your way among Velázquez, Goya and El Greco; better to choose a few rooms than to try to see everything at once. In the afternoon, the Retiro, rowing boats on the lake by the monument to Alfonso XII and the glass Crystal Palace. On day two, the Reina Sofía and Picasso's Guernica, or the Royal Palace, and in the evening the tapas bars around the Plaza Mayor and in La Latina, moving from one counter to the next. Day three is Madrid without a plan: a market, bookshops, a long lunch and a siesta nobody here needs to apologise for.
02Days 4–5 · Toledo
A city of three faiths
About half an hour by train from Madrid, and a night in Toledo's old town itself, after the day visitors have left. Christians, Jews and Muslims lived here side by side for centuries, and it shows at every turn: the former mosque of Cristo de la Luz with its horseshoe arches, two surviving synagogues with Mudéjar plasterwork and a vast Gothic cathedral. In the small church of Santo Tomé hangs El Greco's The Burial of the Count of Orgaz, a painting worth the journey on its own. In the evening, a walk around the river's loop to a viewpoint across the Tagus, where the whole city sits on its rock, and marzipan, made here by nuns for centuries.
03Days 5–6 · Segovia
An aqueduct, an Alcázar and roast suckling pig
This is where the car journey begins: from Toledo to Segovia it's about two hours, skirting Madrid. The town is greeted by the Roman aqueduct, granite arches standing for almost two thousand years, built without mortar. The streets climb to the Gothic cathedral, known for its elegance as the 'lady of cathedrals', and on to the Alcázar, a castle at the tip of the rock whose towers are said to have inspired more than one fairy-tale castle. From the top of the tower you can see the plateau and the Guadarrama mountains. Dinner in Segovia means cochinillo, roast suckling pig so tender it is traditionally cut with the edge of a plate. One night here, and in the morning it's worth walking around the town low by the river as the first sun lights the Alcázar.
04Days 6–8 · Ávila & Salamanca
Walls, a saint and golden sandstone
About an hour to Ávila, ringed by unbroken medieval walls with nearly ninety towers; you can walk along the top of a section. It's the town of St Teresa, so the convents are serious and the sweets bear her name. In the afternoon, about another hour to Salamanca and two nights. The Plaza Mayor is counted among Spain's finest squares, and in the evening, when the lamps come on, the whole town gathers here: students, families and grandparents. In the morning, the university and its Plateresque facade, where visitors hunt for a tiny frog on a skull, the House of Shells, two cathedrals side by side and their towers, which you can climb. Salamanca also rewards a slow walk without purpose: the sandstone changes colour with every hour.
05Days 8–10 · La Alberca & the Sierra de Francia
Villages beneath the chestnuts
About an hour and a quarter south lies the Sierra de Francia, a biosphere reserve near the Portuguese border, and two nights in a village house or a small hotel. La Alberca was among the first villages in Spain to be declared a historic monument: houses of stone and timber with overhanging balconies, a crooked square and streets that have barely changed in centuries. In nearby Mogarraz, portraits of people who once lived here hang on the house fronts. On day two, the road to the summit of the Peña de Francia, where a sanctuary stands at more than 1,700 metres, and down into the valley of Las Batuecas with its monastery and rock paintings. In the evening, local ham and wine from the mountain terraces. On the last day it's about three hours by road to Madrid, or the car is returned in Salamanca and the journey continues by train.

Experience highlights

01
The Prado with a guide
Velázquez's Las Meninas, Goya's Black Paintings and El Greco: a few rooms, properly understood.
02
A night inside Toledo
Once the day visitors leave, the narrow streets and synagogue courtyards are yours.
03
Salamanca's Plaza Mayor at night
Lamplit golden sandstone and a whole town gathered in one square.
04
The villages of the Sierra de Francia
La Alberca, Mogarraz and the road to the summit sanctuary: a quiet ending to the journey.

First, we listen. Then, we explore what's possible.

Make it your own

Slower or shorter
For eight days, Toledo becomes a day trip from Madrid and the Sierra de Francia keeps one night; with a spare day, a second night inside Toledo.
With an art or food focus
For art lovers, the Thyssen in Madrid and El Greco's traces in Toledo's churches; for food lovers, markets, a ham farm near Salamanca and wine cellars.
In spring or autumn
April to June and September to October are usually the most pleasant: midsummer on the plateau is hot, and winter cold, sometimes with snow in Segovia.
With Portugal
The Portuguese border is only a few dozen kilometres from the Sierra de Francia, so the journey continues naturally to the Douro valley and Porto.

Practical considerations

The best time is spring and autumn (roughly April to June and September to October). In July and August, afternoons on the plateau are very hot, and winters are cold; the weather varies year to year.
The first part of the journey is by high-speed train from Madrid, the second by car. Rail timetables and stations change (some high-speed stations lie outside the town centre), so we check them before you travel.
We book timed tickets for the major museums and busiest sights in advance; free-entry hours and opening times change, so we check them closer to the journey.
Spain eats late: lunch usually after two, dinner after nine, and some places close in the afternoon.

General guidance only. Seasons, weather and wildlife are never guaranteed, and travel requirements are always worth checking before you go.