Spain: Madrid and Old Castile, from Segovia to Toledo

Fly into Madrid-Barajas Airport (MAD), about 15 km from the centre, where a driver meets you in the arrivals hall and takes you to your hotel near the old city. Plan to land by about 3 pm so you have time to rest. At about 6 pm your See Sight Tours guide meets the group for a short briefing on the week: which days start early, where the free afternoons fall and how the drives are broken up.

Free time: Free until the 6 pm briefing

We walk to the Prado for its 10 am opening, ahead of the tour coaches, and spend two hours inside with a licensed local guide. The visit stays with the Spanish painters you will meet again on this trip: Velázquez's Las Meninas, El Greco's elongated saints (good preparation for Toledo), and Goya, from the bright court portraits to the Black Paintings he made on the walls of his own house. After the guided visit you can stay on in the galleries as long as you like.

Free time: Afternoon free

Activity: About 3 to 4 hours on your feet in the museum and on the tapas walk, all on level city streets.

A short drive takes us about 50 km north-west into the foothills of the Sierra de Guadarrama to San Lorenzo de El Escorial. Philip II built the monastery and palace in the late 16th century as a royal residence, a monastery and a burial place for the kings of Spain, and it has been on the UNESCO list since 1984. We go in at its 10 am opening with a local guide: the library with its painted vaults, the basilica, the plain apartments where Philip II lived and died, and the Pantheon of the Kings below the altar.

Easier option: Skip the Reina Sofía and take the afternoon at the hotel or in the Retiro park.

Free time: Evening free

Activity: The monastery visit is about 2 hours on foot, with stairs down to the Pantheon of the Kings.

We leave Madrid at about 8:30 am and drive about 90 km, an hour and a quarter, through the tunnels under the Sierra de Guadarrama to Segovia, where the old town and its aqueduct have been on the UNESCO list since 1985. The first stop is the Roman aqueduct itself, about 28 m high at its tallest in the Plaza del Azoguejo, built of granite blocks without mortar around the end of the 1st century AD. From there we walk up through the old town with a local guide to the Cathedral, one of the last Gothic cathedrals built in Spain, and along the ridge to the Alcázar, the castle on the rock above the meeting of two rivers. Climb the Tower of Juan II for the view of the plains.

Easier option: Skip the tower climb and take the Alcázar's palace rooms at your own pace.

More active option: Climb the 152 steps of the Tower of Juan II at the Alcázar for the view over the old town and the plains.

Free time: Late afternoon and evening free

Activity: Segovia sits at about 1,000 m, so evenings are cool even in spring and autumn. About 3 hours on foot, with some steep lanes.

An hour's drive west, about 67 km, brings us to Ávila, the highest provincial capital in Spain at about 1,130 m, ringed by medieval walls with about 87 towers and nine gates that are among the most complete in Europe. We walk a section along the top of the walls with a local guide, then visit the Cathedral, whose apse is built into the walls like a fortress tower, and the streets where Saint Teresa of Ávila was born.

Easier option: Stay at ground level and walk the outside of the walls to the Puerta del Alcázar instead of the climb to the top.

Free time: Evening free in Salamanca

Activity: The walls have steep steps at the access points and uneven paving on top. Ávila is the highest point of the trip, about 1,130 m. From late October to late March the walls close on Mondays; departures in those months are set so this day never falls on a Monday.

Salamanca's university, founded in 1218, is one of the oldest in Europe. We meet at about 9:30 am to walk to its Plateresque facade, carved in stone like lace, where students still search for the small frog on a skull for luck, then visit the Old and New Cathedrals, which stand side by side, and climb the Ieronimus towers for the view across the rooftops.

Easier option: Skip the climb up the Ieronimus towers and wait in the Patio Chico garden between the cathedrals.

Activity: The longest drive, about 3 hours plus a coffee stop, so we start with a morning on foot and lunch before we go.

Toledo, on the UNESCO list since 1986, is at its quietest before the day-trippers arrive from Madrid, and you are already inside the walls. We walk the empty lanes early with a local guide, then go into the Primate Cathedral at its 10 am opening: Gothic outside, and inside a crowd of chapels, the gilded altarpiece and the Transparente, a Baroque burst of light cut through the vault. From there it is a few minutes to the church of Santo Tomé, where El Greco's Burial of the Count of Orgaz still hangs in the chapel it was painted for, and on to the Synagogue of Santa María la Blanca with its rows of white horseshoe arches. At about 1 pm we drive about 95 km, an hour and a quarter, to Madrid-Barajas Airport, or to central Madrid if you are staying on. Book a flight that leaves after about 5 pm.

Easier option: For a flight before about 4 pm we leave Toledo after the Cathedral.

Activity: Book a flight leaving Madrid after about 5 pm to see all of Toledo. About 2.5 hours on foot on steep, cobbled lanes.