Why go now?
Cultural, cutting edge and full of character: the Portuguese capital lays on centuries of history, then throws in barrios that bubble with bohemian flair and forward-thinking projects such as the transformation of neglected buildings by large-scale urban artworks ( cargocollective.com/crono). A stand-out example is on Avenida Fontes Pereira de Melo (1). Bolstering the city's style-maker quotient is Experimenta Design ( experimentadesign.pt; until 27 November), a festival of modern aesthetics and diverse events that started earlier this week.
I flew to Lisbon from Luton with easyJet (0843 104 5000; easyJet.com), which offers one-way fares from £26.99 and also flies from Gatwick, Bristol, Edinburgh and Liverpool. Lisbon is also served by TAP Portugal (0845 601 0932; flytap.com/UK) from Heathrow, Gatwick and Manchester; by BA(0844 493 0787; ba.com) from Heathrow; and by Bmibaby (0871 224 0224; bmibaby.com) from Manchester (Mar-Oct).
The airport is 7km north-east of the city. The easiest way into town is on the Aerobus ( carris.pt), which departs every 20 minutes between 7am-11pm, stopping at a dozen destinations, and terminating at Cais do Sodré train station (2). A single fare is €3.50 (free for TAP Portugal passengers on presentation of a boarding pass), taking 25-30 minutes. The ticket is valid for the rest of the day on the city's bus network. A taxi is marginally faster, costing around €15.
Get your bearings
Like Rome, Lisbon is set on seven hills, but pre-dates the Italian capital by about 400 years. The city shoots up either side of the flat Baixa district, which channels down towards the broad, Tagus river. An epic earthquake destroyed much of the city (and around 35,000 lives) in 1755. Lisbon was then redesigned by the then-prime minister, the Marques de Pombal – most notably Baixa, as a district of broad avenues and spacious squares. Moorish quarters, or barrios, still mark out the hills: the Bairro Alto (nightlife) and Chiado (shopping) on the west, and multi-cultural Mouraria, ancient Alfama and Castelo, with the 12th-century Sao Jorge Castle (3), to the east.
The transport system comprises a four-line metro (metrolisboa.pt), buses (carris.pt) and idiosyncratic trams, many of them more than 100 years old. The easiest way to get around is with a one-day travel card (€4.60; first buy a rechargeable card for €0.50). The Lisbon Card (€17.50 for 24 hours) is available from the tourist office (4) on Praca do Comercio (00 351 210 312 7000; askmelisboa.com; daily 9am-8pm).
Four Seasons Ritz Lisbon (5) at 88 Rua Rodrigo da Fonseca (00 351 21 381 1400; fourseasons.com/lisbon) lives up to expectation. Huge rooms overlooking Parque Eduardo VII (6) and old-fashioned glamour set the scene, while a swanky spa and high-hitting restaurant, Varanda, keep things current. Doubles from €320, including breakfast.
Design junkies should check into Fontana Park (7), providing sharp lines and dark hues in a converted metalworks at 2 Rua Engenheiro Vieira da Silva (00 351 21 041 0600; fontanaparkhotel.com). Doubles from €90, B&B.
Lisbon frequently tops worldwide hostel polls; Traveller's House (8) has won the "Hoscars" for the last four years. Located at 89 Rua Augusta (00 351 21 011 5922; travellershouse.com), it offers dorm beds for €18 and doubles from €54, both with breakfast and lashings of style.
Take a hike
Start at Parque Eduardo VII (6), a sloping ribbon of green – named after the English king who visited in 1902 – that ends at Praca Marques de Pombal (9), with its bronze statue of the Portuguese prime minister. Continue south down Avenida da Liberdade, the 90m-wide boulevard modelled on Paris, lined with the likes of Prada and Armani and shaded by a canopy of trees. The road ends at Praca dos Restauradores (10), a touristy congregation of eateries.
Continue south to Praca Dom Pedro IV (11), also known as Rossio, a large square dedicated to Pedro IV of Portugal, the first ruler of the empire of Brazil – note the iconic black and white wave mosaic floor, also seen beside Rio de Janeiro's beaches.
Cross to the square's eastern periphery and continue south down Rua Augusta, a busy, pedestrianised thoroughfare lined with old-fashioned shops. Head under the arch built to commemorate the 1755 earthquake and finish at the Praca do Comercio (4), an enormous square that ends at the mighty Tagus.
Take a view
Switch back up Rua do Ouro and stop at the 45m-tall iron monolith that is the Elevador de Santa Justa (12). Built by an apprentice of Gustave Eiffel in 1902 to connect Baixa with the lofty Largo do Carmo, the lift and viaduct now double as a tourist attraction (00 351 21 361 3054; carris.pt) offering elevated views of the city. Returns €5, or use your travel card. Open daily 7am-9pm.
Lunch on the run
Jose Avillez's CV takes in stints with Ferran Adrià and Alain Ducasse and a Michelin star at Lisbon-lux restaurant Tavares. Now, in Chiado, the young chef has created an informal address of his own with Cantinho do Avillez (13) at 7 Rua dos Duques de Braganca (00 351 21 199 2369; cantinhodoavillez.pt). Contemporary Portuguese dishes such as steak sandwiches, Alentejo-style black pork (both €7.50) and scallops with avocado (€7.25) are served in a perfectly pitched atmosphere of laid-back sophistication.
Chiado is Lisbon's elegant and easy-going shopping district. On the pedestrianised Rua do Carmo (14) H&M, Footlocker and a bustling mini-mall jostle for space with stand-out stalwarts such as Luvaria Ulisses at number 87a (00 351 21 342 0295; luvariaulisses.com), which has been selling hand-made gloves since 1925. Around the corner at 7 Rua Garrett, Paris em Lisboa (15) is a wood-fronted shop dating back to 1888, specialising in linen (00 351 21 346 8885).
Shoot skywards at the Tivoli Lisboa hotel (16), 185 Avenida Liberdade (00 351 21 319 8900; tivolihotels.com) to the rooftop, where you emerge from the lift at the Euro-chic Sky Bar. The sunset views are breathtaking, encompassing the pink-tinged city as it shelves into Baixa and down towards the Tagus. An Absolut Vanilla in the Sky cocktail costs €10.
Dining with the locals
Plywood walls and black tiles offer a modern take on Portuguese dining at the sleek Restaurante 560 (17), 78 Rua das Gaveas (00 351 21 346 8317; restaurante560.com). Taking its name from the barcode prefix that identifies Portuguese products, it offers a Lusitanian-focused menu that starts with octopus carpaccio or grilled fig and goat's cheese salad and works its way through black spaghetti with prawns and cuttlefish, and partridge pie, to finish with pineapple and coriander sauce. A three-course meal for two with wine costs around €70.
Sunday morning: out to brunch
Deli Delux (18) at 8 Avenida Infante D Henrique (00 351 21 886 2070; delidelux.pt) is a bourgeois food emporium with a small café that spills onto a terrace, sometimes right up against docked cruise ships. Nevertheless, it's a popular spot and offers fresh continental breakfast for €9.50, or €13 if you add scrambled eggs with Serrano ham, smoked salmon or asparagus (10am-4pm at weekends).
Go to church
Continue along the Tagus and weave up through the sinuous roads of Alfama, beneath washing-bedecked windows, to the Se (19), Largo da Se (00 351 21 887 6628), the much-modified 12th-century cathedral built by the first king of Portugal. The two imposing bell towers give it the impression of a medieval fortress and indeed the interior is a little austere. However, a mother-of-pearl safe contains the relics of the city's patron saint, St Vincent and sections of the mosque that it was built over have now been uncovered. Open daily 10am-7pm, free (though visiting the cloisters costs €2.50).
From Se (19), wind uphill to the Castelo district and the Sao Jorge Castle (3). This is where Lisbon was first occupied during the Iron Age. Pass under the Arch of Sao Jorge and wander the pretty residential streets inside Castelo's walls (sections of which date back to Roman times), then into the Castle (3) (00 351 21 8800 620; castelosaojorge.pt; daily 9am-6pm; €7). Explore the ruins of the 14th- to 16th-century royal residence, the 10 towers and camera obscura, then make for the main square, with its old cannons and impressive city views.
Take a ride
Head back in the direction of the Se (19); just before you round the corner to the cathedral, hop aboard tram number 28 ( carris.pt). Built of wood and chrome in the early 20th century, the yellow cars clunk their way down past the cathedral, swerving down vertiginous roads and dipping down into Baixa before clambering their way back up to the Bairro Alto. Watch your valuables on board.
A walk in the park
Get off the tram at Santa Caterina and walk up Rua do Seculo, through the romantic Praca do Principe Real (20) and across to the Botanical Gardens (21). The gardens (00 351 21 392 1893) at Rua da Escola Politecnica are accessed via an avenue of palm trees. Enter a haven of shady walkways, beds planted with 10,000 exotic trees, plants and shrubs and a large pond full of ducksand lily pads. Open 10am-6pm on Sundays, 9am-6pm other days; €1.50.
The icing on the cake
From Cais do Sodre station (2) board a train to Cascais. The 40-minute trip (€3.90) takes you on a scenic journey along the Tagus towards the Atlantic. Landmarks along the way look familiar, even to the first-time visitor – the 25 April suspension bridge is a doppelganger for the Golden Gate Bridge (and built by the same company) and Cristo Rei could pass for Rio de Janeiro's Christ the Redeemer. You'll also pass the fairytale Belem Tower, languishing just offshore, as well as the enormous gothic-renaissance Jeronimos Monastery. The train pulls into the pretty little seaside resort of Cascais, with sandy coves ideal for soaking up the sun, or sunset.