Fourteen days from Madrid to Lisbon: the old road west

Get in, drop bags and go to the middle. Plaza Mayor is an enclosed rectangle of arcaded brick with nine gates, built outside the medieval walls in the seventeenth century, and it has been used for bullfights, markets, royal proclamations, autos-da-fe and executions. It is now cafes and tourist shops, and it is still the right first sight of the city, particularly through the Arco de Cuchilleros in the south west corner.

Five minutes east is the Puerta del Sol, which is the actual centre: the kilometre zero plaque from which every Spanish road is measured, the clock the whole country watches on New Year's Eve, and a permanent crowd. Look at it, do not linger.

Then the Mercado de San Miguel, an iron and glass hall from 1913 just off the Plaza Mayor, now a food market rather than a produce market and unashamedly aimed at visitors. Go anyway, early in the evening, have a couple of things and a glass of vermouth standing up, and use it as a starter before dinner somewhere on Cava Baja at ten.

Give the morning to the museums. Three of them stand within a kilometre of each other on and around the Paseo del Prado: the national collection with its Velazquez, Goya and Bosch, the Thyssen next door filling in everything the Spanish crown never bought, and the Reina Sofia at the bottom of the hill with Guernica in it. Nobody sees all three properly in a day. Pick one for the morning and put a second in after lunch if you have the appetite.

The Reina Sofia is the one to pick if you can only do one, and not because it is better: Guernica is hung in a room of its own with the preparatory sketches around it, and standing in front of a painting that size with the drawings that made it is worth more than another gallery of court portraits.

In the afternoon walk into the Retiro, which starts directly behind the Prado. It is a hundred and twenty hectares of formal park with a boating lake, a rose garden and a pavilion made entirely of glass, and on a Sunday there are drum circles and puppet shows and half of Madrid in it.

Finish at the other end of town at the Royal Palace, which has three thousand rooms and is the largest working royal palace in western Europe, though the king does not live in it. Go at the end of the day for the light on the Plaza de Oriente rather than for the queue at four.

Thirty three minutes on the train from Atocha and you are in a city on a granite spur inside a loop of the Tagus, which was the capital of Visigothic Spain, then a Moorish city, then the seat of the Castilian court until Philip II moved it to Madrid in 1561, and has been essentially frozen since.

Go to Santo Tome first, before the coaches. It is a small parish church holding one painting: El Greco's Burial of the Count of Orgaz, painted in 1586 for the chapel it still hangs in, showing a local nobleman being lowered into his tomb by two saints while the entire cast of contemporary Toledo watches. It is the best argument anywhere for seeing a painting in the room it was made for.

The cathedral is five minutes away and is the other reason to come: a French Gothic cathedral begun in 1226 on the site of the great mosque, with a sacristy full of El Grecos and a baroque skylight cut through the vault behind the high altar that looks like a special effect and was built in 1732.

Then the Jewish quarter. Santa Maria la Blanca was built as a synagogue in the twelfth century by Muslim craftsmen for a Jewish congregation under a Christian king, which is the whole history of this city in one building, and it was later a church. Horseshoe arches, whitewash, and nothing else in it.

An hour and forty minutes from Chamartin across the Castilian plateau, and Salamanca appears as a low gold town above a river. The station is fifteen minutes' walk from the centre.

Go straight to the Plaza Mayor, which was finished in 1755 and is the reason people come: an enclosed baroque square with arcades on all four sides, medallions of Spanish kings and other notables set into the spandrels, and a town hall on the north side. It is the social centre of the town rather than a monument, and at eight in the evening every student in Salamanca is in it.

Then the cathedrals, which are two buildings joined at the hip. You enter the new one, begun in 1513 and still Gothic in a century that had moved on, and walk out of a side door into the old one, a squat twelfth century Romanesque church with a dome of overlapping scales. On the newer building's Puerta de Ramos, a restorer in 1992 carved an astronaut into the stonework, and finding it has become the town's small game.

Cross the Roman bridge at the end of the afternoon. Fifteen of its arches are original, it carried the Via de la Plata, and from the far bank the whole town stacks up behind the river in exactly the light the stone was made for.

The university's Escuelas Mayores has a facade covered in carved stone so fine it looks stamped rather than cut, and somewhere on it, on a skull, sits a small frog. Finding it without help is a rite of passage and students will tell you it guarantees you pass your exams. Inside, the lecture hall of Fray Luis de Leon is preserved with its original benches, and the old library above the courtyard holds tens of thousands of books printed before 1800.

Two minutes away is the Casa de las Conchas, a fifteenth century mansion whose facade is studded with more than three hundred carved scallop shells, the badge of the order its owner belonged to. It is a public library now, which means you can walk into the courtyard for nothing and sit in it.

In the afternoon, the Convento de San Esteban, a Dominican monastery begun in 1524 with a facade carved like an altarpiece and a staircase inside by Diego de Siloe. Columbus lodged with these friars while he was trying to get his voyage funded, and they argued his case at court when the university's own committee had turned him down.

Then back to the square for the evening, which in Salamanca genuinely is the plan.

The coach leaves Salamanca in the morning and takes about four hours down the A-66 through Extremadura, which is oak pasture, black pigs and very little else for two hundred kilometres. It follows the line of the Roman road, the Via de la Plata, which is what put every town on this route where it is.

Merida in the afternoon is easy, because everything is in the middle of it. The Templo de Diana is a first century temple that was never actually dedicated to Diana, standing in a small square with most of its columns still up. In the sixteenth century a nobleman built a Renaissance palace inside it rather than knocking it down, and the two are still fused together, which is worth the visit on its own.

Five minutes downhill is the Alcazaba, a ninth century Moorish fortress thrown up on the bridgehead out of recycled Roman blocks, with a cistern in the middle reached by a double staircase lined with Visigothic carvings. Everything in this town is made out of the thing before it.

Then walk twenty minutes north to the Acueducto de los Milagros, a stretch of aqueduct three tiers high in granite and brick stripes, running across a park at the edge of town. White storks nest on the top of it in spring and they are enormous and completely unbothered.

Buy the combined ticket at the theatre entrance and start there. The Roman theatre was built around 15 BC by Agrippa, held six thousand people, was buried to its upper tiers for centuries and excavated from 1910, and its stage wall is still standing two storeys high with its columns and statues in place. It is the single most complete Roman theatre in Spain and it is still used, every summer, for classical drama.

The amphitheatre is directly next door and shares the ticket. It opened in 8 BC, held fifteen thousand, and unlike the theatre it has been left as an oval bowl of stone benches with the animal pens and the drainage channels exposed in the middle. On a weekday morning out of season you will have it to yourself.

Across the road is the National Museum of Roman Art, which Rafael Moneo built in 1986 directly over an excavated Roman street, in brick arches echoing the ruins outside. The mosaics are hung on the walls like paintings, three storeys high, and it is one of the best museum buildings in Spain regardless of what is in it.

The coach goes west to Badajoz, over the Guadiana and into Portugal, and reaches Evora in about four hours including the change. The country on the Portuguese side is the Alentejo: cork oak, wheat, whitewashed villages and almost nobody, and it goes on for the whole journey.

Evora is small and walled and everything is uphill from the gate. Go to the top first, where the Roman temple stands in a square with fourteen granite columns still standing and Corinthian capitals of Estremoz marble. It is first century, it was probably dedicated to the imperial cult rather than to Diana whatever the signs say, and it survived because it was walled up and used as a butcher's shop until 1836.

Behind it is the cathedral, built between 1280 and 1340, which is a fortress with a church inside it: granite, crenellated, two mismatched towers, and a rose window over the door. Climb to the roof terrace, which is the best view in the Alentejo and shows you exactly how small the town is and how large the plain around it.

Then eat. Alentejo cooking is bread-based, pork-based and much heavier than the climate suggests, and it is the best food on this route.

Go out to the Almendres cromlech first thing, fifteen kilometres west on a dirt track through cork oak. Ninety five granite stones stand in two joined ovals on a slope facing the sunrise, raised in stages from the sixth millennium BC, which makes the oldest of them roughly two thousand years older than Stonehenge. There is no fence, no ticket, no building and usually nobody there. Some of the stones have carvings on them and you can put your hand on any of them.

Back in town for the Capela dos Ossos, which is attached to the church of Sao Francisco and is exactly what the name says: a small chapel whose walls and pillars are entirely faced in the bones of about five thousand people, monks and townspeople dug up from crowded cemeteries in the sixteenth century. Over the door is an inscription telling you that the bones inside are waiting for yours. It is not a folly and it was not meant as a horror; it was meant as an argument.

In the afternoon walk the Prata aqueduct, which was finished in 1537 by Francisco de Arruda, who had worked on the Belem tower in Lisbon. It comes into the town over the rooftops and then, where it reaches the streets, the townspeople simply built houses, shops and a cafe into the arches, which are still lived in. Following it out through the walls takes about an hour.

Then a long dinner. This is the last night before the last city.

An hour and a half on the train from Evora, over the Tagus and into Oriente station, which puts you at the eastern end of the city. That is convenient, because the two things worth doing this afternoon are both out that way.

The Museu Nacional do Azulejo occupies a convent founded in 1509 and tells the whole story of the Portuguese tile, from Moorish geometric work through Dutch blue and white to the industrial panels on the metro. The convent church is a gold and tile interior that stops people at the door, and the last room upstairs holds a twenty three metre panel showing the entire Lisbon waterfront as it looked shortly before the 1755 earthquake destroyed most of what is in it.

Then walk fifteen minutes west to the Panteao Nacional. The church of Santa Engracia was begun in 1682 and not finished until 1966, which is why the Portuguese expression for a job that never ends is a work of Santa Engracia. It is a vast white marble dome over a Greek cross, holding the tombs of presidents, writers and a fado singer, and the terrace at the top of it looks over the whole of Alfama and the river.

Eat down in Alfama afterwards, and get an early night. Tomorrow is uphill.

Go up first. The Castelo de Sao Jorge is on the highest hill in the city, on a site that has been settled since the eighth century BC and fortified by everybody who has held Lisbon since. The ticket buys you walls to walk and the whole lower city, the river and both bridges from the ramparts. The first hour after opening is worth setting an alarm for.

Walk down through Alfama, the quarter the earthquake spared, which has no plan at all: lanes a metre wide, stairs everywhere, washing overhead, and the 28 tram grinding past close enough to touch. Stop at the Miradouro de Santa Luzia, a tiled terrace with bougainvillea over it and the whole quarter dropping to the water below.

In the afternoon, Sao Vicente de Fora, started in 1582 and finished in 1629, which is a Mannerist monastery with two things worth the ticket: a cloister covered in eighteenth century tile panels illustrating La Fontaine's fables, and the former refectory, which holds the tombs of nearly every Braganza monarch, the dynasty that ruled Portugal from 1640 until the republic in 1910. They are lined up in a room like furniture.

Keep the evening for fado. It was born in these streets, the tourist versions are on every corner, and the thing to look for is a small room with a cover charge and a rule about photographs.

The train from Rossio takes forty minutes and climbs into a wooded hill range that is wetter, cooler and greener than anywhere else near Lisbon, which is why the Portuguese court and then the nineteenth century rich built here. Buy the Pena ticket before you go and take an early train; this is the busiest place in Portugal.

The Pena Palace is a nineteenth century romantic fantasy in yellow and red on the top of the highest crag, built for Ferdinand of Saxe-Coburg from 1842 on the ruins of a monastery, with Moorish domes, Manueline windows and a drawbridge that does not work. It is absurd and it is wonderful, and the park below it is enormous and almost empty because everybody photographs the terrace and leaves.

Walk twenty minutes along the ridge to the Moorish castle, which is a ninth century wall running along two summits with nothing inside it. That is the point: you walk the wall, up and down, with Sintra below on one side and the Atlantic on the other, and there is no queue.

In the afternoon, down in the town, Quinta da Regaleira is a house and garden built between 1904 and 1910 by a rich collector with an interest in the Templars, the Masons and alchemy. The garden is full of tunnels, grottoes and a spiral initiation well nine storeys deep that you walk down and come out of somewhere else entirely.

Belem is five kilometres downriver, and the reason to go is a single building. The Jeronimos monastery was begun in 1501, paid for by a tax on the spice trade that Vasco da Gama's voyage opened, and built in the Manueline style, which is late Gothic with ropes, corals, artichokes and navigational instruments carved into it. The church is free and the cloister is not; pay for the cloister, which is the finest room in Portugal. Da Gama is buried just inside the west door.

Ten minutes downriver, the Torre de Belem stands in the water: a small fortified tower from the same decade, part lighthouse and part customs post, with a carved rhinoceros head under one of the turrets copied from an animal the king was sent in 1515. The queue is worse than the monastery and the interior is small, so judge it from the causeway if the line is long.

On the way back into town, stop at the Museu Nacional de Arte Antiga, which is the national collection and is unaccountably quiet. It holds Bosch's Temptations of Saint Anthony, the St Vincent Panels that nobody can fully identify, and a set of Japanese folding screens showing Portuguese traders arriving in Nagasaki in the 1590s, painted by people seeing Europeans for the first time.

Then a custard tart, which is the whole point of Belem for a substantial number of visitors.

Spend the last morning in the best museum in Portugal, which most visitors never reach because it is a twenty minute walk north of the centre in a modernist building in its own garden.

Calouste Gulbenkian was an Armenian oil negotiator who took five per cent of the Iraq Petroleum Company and spent seventy years buying art with it: Egyptian sculpture, Islamic manuscripts, Chinese porcelain, Rembrandt, Rubens, Turner, and a room of Lalique jewellery he commissioned directly from the maker. He left the whole collection to Portugal, which had given him refuge in the war, and the foundation built this to hold it.

It takes two hours and the garden outside takes another one, with a lake and enough shade to wait for a flight in.

Then the airport, which is fifteen minutes away by metro from the museum's own station, or Oriente for the train back to Spain if the trip is not finished.