Once upon a time there were three fairytale cities, each one very beautiful and steeped in history. The first city rose to fame as a centre for scholarship, establishing one of Europe's earliest universities and earning such a reputation for wisdom that Christopher Columbus made a pilgrimage here to consult the great sages before embarking on his quixotic journey to India. (The sages told him he was wrong…) The second rode to riches on the sheep's back; in the 15th century it became a medieval powerhouse fuelled by a flourishing wool trade. The third made its name as a political and religious force, the birthplace of Catholic Spain and a vibrant centre of European art and literature.
Salamanca, Segovia and Toledo are just three of the nine UNESCO World Heritage locations within striking distance of the Spanish capital, Madrid. If you have limited time it's difficult to choose which ones to visit; we opted for these three because we had five days at our disposal and they seemed the most manageable. Each has parlayed its richly layered past into a compelling present-day tourist attraction, worthy of a detour.
What follows is a potted guide to each city with some suggestions of what to do while there. Toledo and Segovia are an easy day trip from Madrid but both merit a little extra time. Salamanca is about 200km from the Spanish capital and takes almost three hours to reach by car so it's better to stay overnight. There's plenty to see and do.
The author Miguel de Cervantes once described Toledo, cultural capital of Spain's north, as "this most precious jewel", and it's a description that remains apt today. The most evocative of the three World Heritage sites featured here, Toledo is a citadel rather than a city, protected by stone walls and the natural moat of the Tagus River. Its architecture is monumental, as seen in the fortress-palace of the alcázar, the gothic cathedral and the monastery of San Juan de los Reyes, commissioned by the Catholic monarchs Ferdinand and Isabella to commemorate Spain's victory over Portugal (just 120km away) in the Battle of Toro in 1476.
They are just some of the many reminders of the city's illustrious past as a political powerbroker and a multi-faith society of Christians, Moors and Jews. The first ruling civilisation at Toledo was Roman, followed by the Visigoths, Moors, Christians, the Moors again and then the Christians again. King Recaredo declared Catholicism the official religion of Spain here in the year 589. Under Alfonso VI, the city became known as "The Imperial Toledo", and Emperor Charles V nurtured its reputation as an axis of European art. Toledo's fortunes waned in the 15th century after Ferdinand and Isabella established a travelling court that eventually settled in Granada. (In 1561 Philip II transferred the court permanently to Madrid, which became the official capital of Spain in 1607.)
It's as if Toledo has existed in a time capsule since then. The historical centre is peppered with remnants of its Roman, Visigoth, Moorish and Christian past and the entire walled city has been declared a national monument. It's a wonderful place.
EAT & DRINK
Adolfo Muñoz is the culinary king of Toledo, with no fewer than three restaurants (including his signature fine diner, Adolfo, and funky wine bar, Adolfo Colección), a cooking school and a respected vineyard. Calle de la Granada 6, +34 925 227 321
A mouth-watering deli stocking mostly local produce - La Mancha wines, olive oil, pâtés (pheasant, hare, wild boar) and soft-ripened oveja (sheep's) cheese. Hombre de Palo 5, +34 925 222 614
Casón de Los López de Toledo
This restaurant in a 16th-century building features a dining room decked with antiques and a menu stacked with delicacies such as Calasparrarisotto with pig's trotter and artichokes. Calle de la Sillería 3, +34 902 198 344
Santo Tomé Obrador de Mazapán
Famous purveyors of marzipan since 1856. Calle de Santo Tomé 3, +34 925 223 763
Friendly Basque tapas bar serving simple pintxos (tapas) washed down with vermouth straight from the barrel. The basement contains the remains of a Roman well. Plaza de Ropería 1, +34 925 257 232
SEE & DO
Roman fortress spectacularly reconstructed as a palace by Carlos I in the 16th century. Demolished and restored many times, most recently during the Civil War. Cuesta de Carlos V, +34 925 238 800
Beautiful portal rebuilt in 1550 with two round towers, crowned by a two-headed eagle, the symbol of Toledo. Calle de Alfonso VI
The Tagus is forded by several charming bridges including the 13th-century Saint Martin, which bears the bas-relief arms of the city of Toledo, and the Alcántara, built by the Moors in 866.
Santa Maria Cathedral
Said to be the richest cathedral in Spain, this gothic marvel's sacristy houses paintings by Goya, Rubens and El Greco. Calle del Cardenal Cisneros, +34 925 222 241
House and Museum of El Greco
El Greco lived in Toledo from 1577 until 1614. Several of his works are here but check it's not closed for renovations. If it is, you can still see his famous Burial of Count Orgaz at Santo Tomé church. Calle de Samuel Levi (no number).
The place for all your weaponry needs. Swords, specifically, from repro medieval numbers to Templar and duelling varieties. Calle de la Ciudad 19, +34 925 222 634
Hotel Palacio Eugenia de Montijo Renaissance palace once home to an empress, now a 40-room five-star hotel with a spa and the Belvis restaurant, overseen by Adolfo Muñoz. Doubles from $130. Plaza del Juego de Pelota 7, +34 925 274 690
This hilltop government-run hotel has the best views of the city. Toledo sparkles at night from the terrace bar and restaurant, which serves specialties from Castile and La Mancha. Doubles from $230. Cerro del Emperador, +34 925 221 850
AC Ciudad de Toledo
Set in a valley beside the Tagus, this former tile factory has 49 rooms and a balcony restaurant with views to the city. Doubles from $130. Circunvalación Hwy 15, +34 925 285 125
There are 10 fast trains a day between Madrid's Atocha station and Toledo. The journey takes 35 minutes. Buses depart Madrid every 30 minutes between 6am and 10pm from the South Station.
Segovia's crowning beauty is its picture-perfect medieval fortress, a fortification so romantic it was reputedly the inspiration for Disney's Sleeping Beauty castle. The fortress, or alcázar, stands guard at the tip of this hilltop stronghold, still protected by much of its original eighth-century walls.
The city achieved fame and fortune in the wool boom of the 15th century, a golden era when textile riches funded much of Segovia's noble architecture and kings ran their affairs from the alcázar. The King's Room inside the fortress records every Spanish regent between the eighth and 15th centuries, from King Pelagio - who launched the reconquest of Spain from the Moors - to Joanna the Mad, the jealousy-stricken wife of philandering Philip the Handsome.
The city's other remarkable monument is a towering Roman aqueduct built around 50AD to channel fresh water from the nearby mountains to the good citizens of Segovia. It is an impressive sight and, together with the collection of Romanesque churches, the magnificent golden cathedral and buzzing bars and cafés, makes Segovia's historic centre a pleasure to explore.
EAT & DRINK
Café-Bar El Bohemío
An intimate bar decorated like a cluttered bachelor pad, with the party ambience to match. Calle del Cronista Lecea 12, +34 921 463 223
Mandala Asian Lounge Bar
Typically Spanish bar serving all-day food and alcohol in unexpectedly sultry surrounds of red velvet, wood lattice and Morrocan pendulum lamps. Calle de Colón 7, +34 610 506 383
The mannered décor and service belie chef Silvano Hernando's avant-garde take on Castile and León staples, such as his mini-hamburger of suckling lamb. Paseo Ezequiel González 25, +34 921 461 545
Mesón de Cándido
The legendary, late Cándido was given the title of "greatest innkeeper in Castile" by King Juan Carlos I, and it's an honour his son continues to hold today. Sophia Loren, Grace Kelly and Antonio Banderas have all feasted on Cándido's fabled roast suckling pig. Azoguejo 5, +34 921 425 911
Chef Julio Reoyo gives Segovian fare a Michelin-starred makeover in dishes such as confit suckling pig with cinnamon-stewed apricots. Plaza Mayor 10, +34 921 461 742
SEE & DO
The quintessential castle, complete with drawbridge and moat. It was once a summer palace for the Castilian kings and is thought to be built on a Roman fortress.
Believed to have been built in the first and second centuries to transport fresh water 19km from the Acebeda River to the city. The only significant remains of Segovia's Roman past.
La Granja de San Ildefonso
In this village 11km from Segovia sits an 18th-century palace built by the Bourbon king Philip V as a summer retreat. The architecture and gardens echo the splendour of France's Palace of Versailles, where he was born. Plaza de España 17, San Ildefonso, +34 921 470 019
Church of San Juan de Los Caballeros
Final resting place of the city's noble families, now deconsecrated and home to the Museo Zuloaga, a ceramic arts and painting museum with lovely gardens by the old city wall. Plazuela de Colmenares, +34 921 460 613
St Andrew's Church
Graceful Romanesque church from the 12th century, one of 30 that once stood in Segovia. About 15 remain standing, though some have been deconsecrated.
The Cholesterol Route
A pleasant walking/workout track that snakes below the alcázar into the surrounding forest. Popular with health-conscious Segovians, hence the name. Enter from Calle de San Valentin.
Parador de Segovia Outside the old city but with stunning views of it (especially from the pool), this surprisingly handsome 1970s compound has 113 rooms and all the amenities of a city resort. Doubles from $215. Valladolid Highway, +34 921 443 737
Palacio San Facundo Sixteenth-century palace near the main square with 19 comfortable rooms and very helpful staff. Doubles from $160. Plaza San Facundo 4, +34 921 463 061
Hotel Infanta Isabel Once frequented by Queen Isabel en route to the royal palace of La Granja, and with décor apparently intact from those times. The hotel has dress-circle views over the main square. Doubles from $85. Plaza Mayor 12, +34 921 461 300
GETTING AROUND Trains from Madrid to Segovia take 30 minutes and run frequently between 7am and 9pm. La Sepulvedana bus line runs buses between Madrid and Segovia every half hour between 6.30am and 10.30pm. It also drives to La Granja de San Ildefonso.
Salamanca is the golden city, especially when the late afternoon sun illuminates its delicately carved sandstone façades. Perched above the granite plains of the campo charro, there's an aristocratic elegance to this place that might stem from the fact it has been a renowned centre of scholarship for many centuries.
The University of Salamanca, established in 1218, is Europe's fourth oldest after Bologna, Paris and Oxford - the "four lights of the world," according to Pope Alexander IV. The city's religious and civil buildings are the height of Spanish and European art, as seen in the intricate sandstone sculptures of its Plateresque university. There are two superb cathedrals, simply known as The New and The Old. These conjoined houses of worship are in the baroque/gothic and Romanesque styles respectively and together they form an emphatic statement of church power in the city.
The university has a similar gravitas. Salamanca produced the father of international law, Francisco de Vitoria, and enticed Columbus to visit for four months in 1487 to debate his trailblazing route to India with a university-appointed council of elders.
This is not to say Salamanca is some dull museum piece. A quarter of its 160,000 inhabitants are students so the place is constantly lively. Its bars and pubs hum with the vigour of youth and its Plaza Mayor is the archetypal main square, always busy and a delight to look at.
EAT & DRINK Víctor Gutiérrez Brilliant Michelin-starred restaurant owned by the Peruvian Gutiérrez; his passionfruit purée with mango dice, raspberry coconut ice-cream and violet is in-cred-i-ble. Calle de San Pablo 66, +34 923 262 973
Valor chocolateria Visit this sweet Spanish chain for chocolate, churros and home-baked treats. Calle de los Libreros 12, +34 923 266 421
Spain's finest hams and sausages, from nearby Guijuelo. Calle de Rúa Mayor 13, +34 923 211 874
Enjoy institutional dining in the rear salon or relaxed tapas and drinks in the front bar. Plaza Mayor 19, +34 923 281 487
El Reloj de la Plaza
Typical Plaza Mayor tapas bar known for its huevos rotos, "broken eggs", a deliciously messy fry-up of egg, potato and chorizo. Plaza Mayor 10, +34 923 216 093
For local delicacies such as Salamancan wines, handmade liqueurs and yemas, tiny sugar and egg yolk cakes first made by the Benedictines. Calle de Rúa Mayor 23, +34 923 218 900
SEE & DO
Casa Lis A museum of decorative arts (dolls, chryselephantine and glassware are its strongest suits) housed in a magnificent art nouveau mansion. Next door you'll find the General Archive of the Civil War, a sobering anthology of documents from that dark time. Calle de el Expolio 14, +34 923 12 14 25
Beautiful boots, belts and leather, handmade for the farmers of the surrounding campo charro. Calle de Rúa Mayor 32, +34 923 215 900
This handsome stone span across the river Tormes is thought to date from the reign of Emperor Trajan, circa 89AD.
The $5 entry fee includes a tour and entry to the towers and rooftop balconies for starling's-eye views over Salamanca.
AC Palacio de San Esteban
A smart conversion of the 16th-century San Esteban convent with a modern wing. Its 51 rooms overlook the rooftops of the historic centre. Doubles from $140. Arroyo de Santo Domingo 3, +34 923 262 296
Two-storey aristocratic home converted into a classic, contemporary hotel of just 13 rooms with marble bathrooms, fresh flowers and flat-screens. Room 15 has a cathedral view. Doubles from $210. Paseo Rector Esperabé 10, +34 923 218 482
Hacienda Zorita Drop-dead gorgeous estate and vineyard outside Salamanca dating from the late 14th century. This former Dominican monastery has been revived as a 30-room hotel with "wine spa". Christopher Columbus slept here in the 15th century. Doubles from about $110. Salamanca-Ledesma Highway (8.7km mark), Valverdon, +34 923 129 400
There are six trains daily from Madrid, taking two and a half hours. Trains also link Salamanca to Avila, León, Valladolid, Burgos, Bilbao and Barcelona. Matacán domestic airport is 15km from the city. Airport taxis can be scarce; call one on +34 923 250 000.