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The first time I was in Lisbon I stumbled upon a shooting. I was wandering through the narrow streets of the Alfama quarter when I was stopped short by a series of wooden barricades blocking an intersection. On the other side of the barrier stood a stocky, swarthy, thickly moustachioed man wearing a trilby hat and a curiously old-fashioned black suit. He was very still, aiming a pistol at something out of my view. From my subsequent position, under a car, I saw him hold this deadly pose for a further 10 seconds, until someone shouted: "Cut!"

The only thing being shot was a film: I later found out that Marcello Mastroianni was in town. With its boulevards lined with colonial-era mansions, medieval old city and Moorish relics, Lisbon cries out to be a film set. It evokes a powerful sense of ... I just had to stop myself from writing "faded grandeur". This is not only the phrase that every guidebook about the city seems to use, but it is also not very accurate. Visiting Lisboa (its Portuguese name) eight years after the shooting scene, I was struck by how visibly it has jerked itself into modernity. An enormous amount of development, funded in large part by Portugal's entry into the EU, has given the city a decidedly forward-looking, stylish quality.

Lisbon experienced a shaky 20th century as the country dispatched its monarchy by firing squad and exile, endured 30 years of quasi-fascist dictatorship and then shed that in turn in the "bloodless revolution" of 1974. It now seems to be assimilating a fascinating past into an ongoing story. A good place to begin exploring this history is Alfama, the oldest remaining part of the city and the starting point for both my visits.

I most enjoyed allowing myself to get lost in the quarter's cluster of cobbled, precipitous streets, whose 12th century layout makes them too narrow for cars to enter. The district is like a village incongruously stuck in a modern metropolis. It is peppered with tempting hidey-hole cafes and bars, kids playing soccer in wonkily shaped squares and fishwives (genuine ones) sitting on porches frying the ubiquitous cod and shooting the breeze: "Look, Jacinta, more of these bloody tourists!"

Like Britain, Portugal is no longer a colonial power but, unlike Britain, it does not seem to mind. I asked one young Lisboan man in a bar in the Barrio Alto what he thought about Portugal's status in the world.

"Well, you know," he said, with a shrug, "we founded Brazil. That's not bad." Indeed, in the late 15th and 16th centuries Portugal was at the forefront of European expansionism. Its territories in Africa, India and China brought the plunder flooding in and its monarchy was the richest in Europe.

This period of distinctive wealth also saw the advent of Portugal's most distinctive architectural style. Manueline architecture, named after the reigning king Manuel I, is a variation on Gothic with a floridity expressing the material and natural wealth the Portuguese found in their colonial acquisitions. Along with motifs such as ropes, nets and seaweed, which refer to the great sailing feats of colonisation, the designs include botanical elements such as corn, artichokes and laurel leaves, and beasts both real and imaginary.

The UN considers a number of the Manueline buildings, mainly those clustered around Lisbon, to be so significant that it has granted them world heritage status. We began our tour of these sites a few kilometres from the city centre, in Belem. This is now a mellow seaside district, but it was from here in 1497 that Vasco da Gama set sail for India, returning with a cargo of pepper approximately comparable in value then to a modern-day shipload of prime Moroccan hashish.

By the waterside, the Torre de Belem represents Lisbon's purest example of the Manueline style. The tower was built for a thoroughly pragmatic purpose, to safeguard the expeditionary ships from those of jealous rivals, which makes its exuberant exterior design seem all the more indulgent. If you imagine a tank with chrome fender, sunroof and stretch-back fins, you get something of the idea. Its most prominent Manueline note is a thick stone rope wrapping around the entire facade, like a ribbon around a giant Christmas present. A further noteworthy feature is the carving of a rhinoceros poking from an external wall - apparently the first African animal to be depicted in European sculpture.

Five minutes' walk from the tower stands another Manueline classic and one of Portugal's greatest monuments: the Jeronimos monastery. As a third-generation atheist I have tended to feel a certain rebellious frisson in the many and varied temples to higher powers that I have visited throughout the world. However, I realise at the same time that, for much of human history, passion and creativity were necessarily expressed through a religious frame.

Jeronimos is a heavenly example of such expression - a kind of poem written in limestone to the awesome novelty of the new world. I was particularly struck by the church's six slender columns branching into fine rib-vaulting at the ceiling, which you realise after staring at them for a while (and with a little help from your guide) are meant to be nothing other than palm trees. The walls are thick with naturalistic carvings that seem to portray the journals of wandering Vasco, whose tomb lies inside. The carving loses all restraint in the inner courtyard, a petrified bestiary complete with dragons, griffins and a leering assortment of gargoyles.

At the risk of blasphemy I must also recommend a visit to a shrine promising earthly, rather than spiritual, satiation in the form of the Antiga Confeitaria de Belem (Rua de Belem 90), a mere stroll from the monastery. This bakery and cafe, a rabbit's warren of rooms in exquisite blue azulejos tile, packed to the gullet with Lisboans, specialises in pasteis de nata. These sublime little tarts of flaky pastry surrounding a dollop of custard are served warm, and you sprinkle them with sugar and cinnamon at your table. The confeitaria has been making them to a prized secret recipe since 1837 and now serves up 10,000 a day.

My Belem bakery experience confirmed me in my belief that Portugal leads Europe in confectionery concoction. German tarts are comforting but lean towards the dowdy; the French are dainty yet perhaps too delicate; the Italians risk being excessive. Portuguese tarts are unalloyed pleasure - the sensual, sticky underbelly of all that Catholicism.

Byron famously called Sintra a "glorious Eden" and, although he was wont to gild anything from boys' bottoms to Greek nationalism, this hilltop town outside Lisbon really is paradisiacal. The former summer residence of Portugal's royalty, it boasts a pleasantly breezy climate due to its elevation and a beautiful old town surrounded by thick woodland. If you make only one day trip from the capital, you should come here; trains run regularly from Rossio station.

Among Sintra's important historical sites, the Quinta da Regaleira is perhaps the most striking. This luxurious 19th-century estate was the fancy of the fabulously rich coffee heir Carvalho Monteiro.

"Moneybags Monteiro", as he was popularly known, had numerous artistic interests and engaged the Italian architect and set designer Luigi Manini to realise them in his fantastical home. The principal residence is thus a compelling, if sometimes overwhelming, exercise in architectural eclecticism including Gothic, Renaissance and neo-Manuelin styles.

Don't miss Moneybags's initiation well in the gardens. A moss-covered, spiral stone staircase leads down to the bottom of the well, 27 metres below. There, a tunnel hewn into the rock takes you eventually to the open air and the artificial Paradise Lake. Moneybags meant the well to refer to Masonic and Knights Templar initiation ceremonies, although Freud might also have had something to say about this inverted tower bored deep into the earth.

Some magnificent examples of the architecture that Monteiro sought to revive lie a further hour north from Lisbon. The Convento de Cristo is the most important Renaissance building in the country and was originally the Portuguese headquarters of the Knights Templar and the Knights of Christ. These two martial orders slashed and torched for Christendom, in a way that sounds oddly familiar, and helped to wrest Lisbon from the Moors in the 12th century.

Nearby, the 13th century Alcobaca monastery was home to less active men of god. For centuries monks lived and prayed here under a vow of silence, communicating by hand gestures. An enormous kitchen built in the 17th century to feed the 300 resident brothers is an impressive sight in itself. This pre-industrial cafeteria is dominated by a huge soaring chimney and also contains voluminous marble fish tanks built in the flow of a local river in order to keep the stock fresh.

I hoped the kitchen brought the monks some relief from their austere-sounding existence; the monastery put me in the mood for more hedonism, and I headed back to Lisbon for another bout of pleasure at the Confeitaria de Belem.

A version of this article first appeared on Guardian Unlimited.

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