Despite its reputation as one of Spain’s greatest cities, TOLEDO can, in some ways, be a bit of a disappointment. Certainly, it’s a city redolent of past glories, and is packed with sights - hence the whole city’s status as a National Monument and UNESCO Patrimony of Mankind - but the extraordinary number of day-trippers has taken the edge off what was once the most extravagant of Spanish experiences. Still, the setting is breathtaking, and if you’re an El Greco fan, you’d be mad to miss this city.

In a landscape of abrasive desolation, Toledo sits on a rocky mound isolated on three sides by a looping gorge of the Río Tajo. Every available inch of this outcrop has been built upon: churches, synagogues, mosques and houses are heaped upon one another in a haphazard spiral which the cobbled lanes infiltrate as best they can. To see Toledo at its best, you’ll need to stay at least a night: a day-trip will leave you hard pressed to see everything. More importantly, in the evening with the crowds gone and the city lit up by floodlights - resembling one of El Greco’s moonlit paintings - Toledo is a different place entirely.

Toledo also hosts one of the most extravagant celebrations of Corpus Christi in the country, with street processions and all the works. Other local festivals take place on May 25 and August 15 and 20.

The street layout and labelling in Toledo can be confusing, but the old core is so small that you’ll soon find your way around; part of the city’s charm is that it’s a place to wander and absorb, so don’t overdose on “sights” if you can avoid it. You shouldn’t leave without seeing at least the El Grecos, the cathedral, the synagogues and Alcázar, but give it all time and you may stumble upon things not listed in this or any other guide. Enter any inviting doorway and you may find stunning patios, rooms and ceilings, often of Mudéjar workmanship.

Toledo was known to the Romans, who captured it in 193 BC, as Toletum , a small but well-defended town. Taken by the Visigoths, who made it their capital, it was already an important cultural and trading centre by the time the Moors arrived in 712. The period which followed, with Moors, Jews and Mozárabes (Christians subject to Moorish rule) living together in relative equality, was one of rapid growth and prosperity and Toledo became the most important northern outpost of the Muslim emirates. Though there are few physical remains of this period, except the miniature mosque of Cristo de la Luz , the long domination has left a clear mark on the atmosphere and shape of the whole city.When the Christian king Alfonso VI “reconquered” the town in 1085, with the assistance of El Cid, Moorish influence scarcely weakened. Although Toledo became the capital of Castile and the base for campaigns against the Moors in the south, the city itself was a haven of cultural tolerance. Not only was there a school of translators revealing the scientific and philosophical achievements of the East, but Arab craftsmen and techniques remained responsible for many of the finest buildings of the period: look, for example, at the churches of San Román or Santiago del Arrabal or at any of the old city gates .

At the same time Jewish culture remained powerful. There were, at one time, at least seven synagogues - of which two, Santa María la Blanca and El Tránsito , survive - and Jews occupied many positions of power. The most famous was Samuel Levi, treasurer and right-hand man of Pedro the Cruel until the king lived up to his name by murdering him and stealing his wealth. From this period, too, dates the most important purely Christian monument, Toledo’s awesome Catedral (the city has remained the seat of the Catholic primate to this day).

This golden age ended abruptly in the sixteenth century with the transfer of the capital to Madrid, following hard on the heels of the Inquisition’s mass expulsion of Muslims and Jews; some of the latter responded by taking refuge in Catholicism, becoming known as Conversos . Few Jews remain today, though Samuel Toledano, late president of the Spanish Israelite Community, was descended from a fifteenth-century grand rabbi, his family name considered proof of his descent from Conversos .

The city played little part in subsequent Spanish history until the Civil War and it remains, despite the droves of tourists, essentially the medieval city so often painted by El Greco. Sadly, however, the Tajo, the city’s old lifeblood, is now highly polluted, and its waters greatly depleted by industry and agriculture. And, as in Venice, fewer and fewer people live in the city centre; most who work there prefer to commute from the expanding suburbs.

Toledo has been a byword for fine steel for a thousand years or more and the glint of knives in souvenir shops is one of the first things you’ll notice on arrival. Some have traced the craft back to the Romans and it was certainly a growth industry when the Moors were here. By the seventeenth century, Samuel Butler was complaining that “the trenchant blade, Toledo trusty, for want of fighting was growing rusty”. Today it’s surprising that, except for a modern display in the Alcázar, there’s little to see outside the shops; in these you can still admire attractive damascene steel swords and knives, with handles inlaid with decorative gold and silver filigree.

Toledo’s main turismo (Mon-Sat 9am-7pm, winter closes 6pm, Sun 9am-3pm; tel 925 220 843 , www.jccm.es/turismo and www.diputoledo.es ) is outside the city walls opposite the Puerta Nueva de Bisagra and next to a convenient taxi rank; it has full lists of places to stay, maps showing the monuments, admission times and charges. There’s also a smaller but more central turismo run by the local ayuntamiento in the plaza opposite the cathedral (Mon-Fri 9am-2pm & 4-6pm; tel 925 254 030 , turitoledo@line-pro.es ).

The train line comes to a halt at Toledo but there are bus connections south to Ciudad Real , west to La Puebla de Montalbán and Talavera de la Reina on the way to Extremadura, and east to Cuenca . If you have transport of your own, or fancy slow progress by bus and on foot, the Montes de Toledo , southwest of the city, are an interesting rural backwater.More local excursions, by bus, to the south of Toledo, could include Guadamur (14km from Toledo), whose outstanding castle stands on a nearby hilltop, and Orgaz , once home to the count of El Greco’s masterpiece The Burial of the Count of Orgaz , now a quiet village with a beautiful plaza, a magnificent Baroque church and a small fifteenth-century castle overlooking the main road to Ciudad Real.

By Spanish standards, Toledo’s nightlife is rather tame. You’ll find most late-night bars running along c/de la Sillería and its extension c/de los Alfileritos, west of Plaza de Zocódover. Picaro on c/de las Cadenas is one of the liveliest discobares in town, while La Abadía , c/Nuñez de Arce 3, is a fashionable but civilized bar which serves a large range of foreign beer and attracts an older crowd than most along here.Two alternative places are Broadway Jazz Club , on Plaza Marrón near the Taller del Moro, and La Boîte de Garcilaso , a similar place nearby at the corner of c/Alfonso XII and c/Rojas; both have occasional live jazz.

Out of the tourist season (Sept-March), classical concerts are held in the cathedral and other churches; details can be obtained from the turismo.