The interior of Jeronimos Monastery

Lisbon, the majestic city said to have been founded by the mythical Ulysses, spreads along the banks of the Tagus River and across some 32 square miles of hilly Portuguese terrain.  Its bumbling tentacles spread far into the distance, drawing once autonomous towns into the urban sprawl of Portugal’s biggest city.

At first glance Lisbon seeps history from every brick and cobbled pavement, almost reaching the ranks of Rome in the sheer number of fading monuments glimmering with classical beauty. Take a closer look at your surroundings, however, and a more varied collage of architecture emerges. Against a mountain backdrop the Medieval Castle of São Jorge looms over the busy streets of Baixa, with its advertising slogans and familiar high-street logos, and on the skyline, behind the rust-red 19^th-century 25^th of April Bridge, flashy modern towers and the pinnacle of a steel sailboat construction are anchored in the concrete jungle of Lisbon’s newest district, Parque das Nações.  This latest addition to the Lisbon cityscape was constructed in preparation for Expo 98 and is designed to impress. With a remarkable repertoire of arresting silhouettes modelled on the sea and sailing motifs the Parque das Nações is, however, as rooted in Lisbon’s sea-faring history and lust for discovery as Jerónimos Monastery, where sailors once prayed for mercy and safe passage before submitting themselves to the high seas.

The ancient and modern blend in a startlingly comfortable symbiosis, flamboyant grandeur mixing with chic minimalism. Perhaps it is not so surprising given Lisbon’s long history of architectural inconsistencies. In the Belēm district alone the 16^th century Jerónimos Monastery, laden with fantastical carved creatures and spear-like gothic spires, towers indignantly over scores of terraced apartment blocks with their uniformed exteriors clad in colourful tiles, reminiscent of long-ago Arabesque influence.

Across the main thoroughfare the chiselled tank of stone that is the Centro Cultural de Belēm (CCB), one of Europe’s largest cultural centres, squats on the waterfront, a squalid prison-like building in comparison to the lurid lavishness of the religious sanctuary. Permit yourself to pay each a visit, however, and you will learn that each has a wealth of cultural treasures to offer. While the monastery delights with towering columns and ostentatious gilt, the Berardo Museum of contemporary and modern art (located within the confines of the CCB) presents gems of a far more provoking ilk, ranging from Basquiat to Picasso to Warhol.

Even from the earliest ages Lisbon was a city whose timeline could be traced by the styles of its structures. Evidence of each successive period in Lisbon’s cluttered history is emblazoned across the city, from the fortressed Castle of São Jorge constructed by the Moorish invaders to the post-earthquake re-incarnation of the city in Baixa accomplished by Portugal’s Prime Minister, Sebastião José de Carvalho e Melo. The Moorish-style narrow medieval streets of the Alfama district sit side by side with this downtown district of Baixa, which forms the tourism and shopping hub of the city. Created after the devastating earthquake of 1755, Baixa flaunts the wealth of Lisbon’s one-time monarchy and is home to many grand monuments, such as Gustave Eiffel’s fantastical Gothic-revival Elevador de Santa Justa, which links downtown Lisbon with the trendy Chiado district, made popular in the 19^th century by coffee-slurping intellectuals who frequented the areas’ numerous cafes and bookshops.

One of Lisbon's distinctive yellow trams

Strolling down the bustling Rua Augusta you will be tempted by sun-baked terraces littered with metal chairs and tables that croon alluringly with an invitation to briefly rest your weary legs and sip silky coffee and suddenly, before you know it, the sun will be setting and dinnertime will be upon you. If you are clever, bypass the lure of the bustling commercial streets and delve deeper into Lisbon’s cultural heritage by handing over a paltry €1.45 to catch a mustard-yellow antique tram, which will rattle through the city on jittery tracks as the breeze flutters through the open windows and sunlight flickers through the gaps in the busy building-lined streets. As the tram slows for traffic on the busy main street gaze longingly at the Pastēis de Belēm cafe, which sells traditional custard tarts from a rabbit-warren of blue and white tiled rooms, before wistfully watching the creamy delicacies slip away when the tram again clatters onwards.

As I careered around the bends in my 1930s carriage the warm autumnal sunlight bathed the tile-fronted buildings in Belēm with a spritely energy and gave the monumental edifices in Baixa a regal grandeur. Among haunting dusty alleys and pristine wide avenues I encountered the immaculate Museum of the Orient, a hulking tribute to one-time colonies in Asia, and wondered at the grand Praça do Comércio’s pastel-coloured buildings, reminiscent of St Petersburg’s monumental squares, as I juddered along on my solid wooden bench.

Historical divergence is not only apparent between buildings scattered across the city, however, but also within the buildings themselves, with even the most traditional edifices exhibiting less than conventional characteristics. This is peculiarly obvious at the 19^th century Valle-Flor Palace, now resurrected as the Pestana Palace hotel, where the gold and champagne facade is primarily influenced by French chateaux of the 14^th to 16^th centuries but the interior displays showy gothic flourishes on the carved chairs in the dark, atmospheric drawing room. In the spacious gardens, which overflow with exotic plants with glossy jungle leaves and jewel-coloured petals, a striking contribution from the Portuguese colonies in Asia is also apparent in the form of a delicate crimson tea pavilion. Strolling down the path from my elegant room in the modern wing of the hotel I glided through time and continents as I passed the oriental pavilion en route to breakfast in the divinely French dining room.

The pleasing dichotomy of fading and fresh architecture stretches even to the furthest reaches of Lisbon’s surrounding towns, with the upper-class tourist enclave of Estoril happily mixing the remnants of past glory with flashes of new-fangled innovation. The grande dame of this seaside spot, the extravagant Hotel Palacio Estoril, has deigned to follow this trend, adding to its portfolio the crowd-pulling Banyan Tree Spa, the first European venture from the world-renowned chain.

The romantic Penha Longa estate

Structures further inland are no safer from trendy modernising tastes than the coast, even those that have been inhabited since the 15^th century like the Penha Longa hotel estate on the outskirts of Sintra. Here the Monastery of St Jerome, a salmon-pink suite of religious buildings, is situated alongside the breezily contemporary Arola restaurant, which screeches chic with big, bold monochrome letters. In a defiantly modern setting I supped on traditional delicacies with refreshingly modern twists, such as Bravas Potatoes shaped into miniature cylinders with a squirt of creamy aioli and thinly sliced black pork sprinkled with jalapeño peppers with rich San Jorge cheese. Clearly no-one has told the proprietors that the city is the time-honoured place to break with convention.

Nowhere, however, is the combination of minimalist modernity and flamboyant classicism more striking than from the rooftop of the Altis Belēm hotel, which sprawls luxuriously over Belēm’s elegant harbour like an updated version of an exclusive Long Island beach mansion. Reclining on a cartoon-like boxy sun bed on the roof of this robust cuboid building, all shining and splendid in gleaming glass and tonal grey and diamond-white textured stone, your eye is immediately drawn to the ornate facade of Belēm Tower. Its purpose as a defence against enemy attack is shrouded by its over-accessorised fairytale turrets, the ultimate in 16^th century Portuguese Manueline excess. Here the stark simplicity of modern taste collides with the extravagant excess of a long-past era and delivers the perfect expression of a Lisbon once more looking expectantly into an age of discovery.