Lisbon

Lisbon’s Alfama district, with its labyrinthine alleyways, hidden courtyards and curving shadow-filled lanes, is a magical place in which to lose all sense of direction and delve into the soul of the city. You’ll pass small grocers, brilliantly tiled buildings and cosy taverns filled with easygoing chatter, accompanied by the scent of chargrilled sardines and the mournful rhythms of fado drifting in the breeze. Round a bend and catch sight of steeply pitched rooftops leading down to the glittering Tejo, and you've never been so easily hooked.

Less than an hour by train from Lisbon, Sintra feels like another world. It's a quaint village sprinkled with stonewalled taverns and a whitewashed palace looming over town. Forested hillsides form the backdrop to the story-book setting, with imposing castles, mystical gardens, strange mansions and centuries-old monasteries hidden everywhere among the enchanting woodlands. The fog that sweeps in at night adds another layer of mystery, and cool evenings are best spent wine-stocked and fireside in one of Sintra’s charming B&Bs.

Born in a working-class neighbourhood of Lisbon, the melancholic music of fado has been around for centuries. Despite its years, fado remains a living art, heard in tiny restaurants and elegant music halls alike. A lone, powerful voice coupled with the 12-string Portuguese guitarra are all the tools needed to bring some listeners to tears, as songs recall broken hearts, unfulfilled dreams and lost days of youth. In fado, raw emotion often conveys more than mere lyrics can; even non-Portuguese speakers find themselves moved by great fadistas.

Few Lisbon images are as iconic as those of the city's vintage electric trams. These adorable yellow-and-white elétricos having been shaking, rattling and rolling around the city since 1901 (they were horse-pulled before that). And none of the system's five lines are coveted more than tram 28E, which criss-crosses the city centre between the westside's Campo de Ourique and Martim Moniz, passing many of Lisbon's must-see sights, astonishing lookouts and symbolic neighbourhoods along the way – all for the bargain-basement deal of €2.90!

With the astounding Unesco World Heritage–listed Mosteiro dos Jerónimos and Torre de Belém as its signature sights, the suburban neighourhood of Belém packs a whole lot of 'wow' into a very small area. From the exquisite contemporary art collections to fairy-tale coaches, Belém's museums will dazzle you. From painstakingly preserved Manueline monasteries to Age of Discoveries fortresses, its architecture will floor you. And then, just when you're done with sightseeing, cocktails and pomegranate-pink sunsets await down by the river.

Sweet-tooths the world over come to Lisbon to sample the city's real-deal pastel de nata, the famous egg-custard tarts invented by Catholic monks at Mosteiro dos Jerónimos and most famously served (as pastéis de Belém) at Antiga Confeitaria de Belém since 1837 (and everywhere else in town these days). These crisp pastry nests, filled with custard cream, are baked at 200°C until crusted golden, then lightly dusted with cinnamon on their way to a happy ending in nearly 15,000 mouths per day (50,000 on Sunday).

Some of Portugal’s most captivating works of art are out on the streets – free viewing for anyone who happens to stroll past. A great legacy of the Moors (and originating from Egypt), the azulejo (hand-painted tile) was adopted by the Portuguese and put to stunning use over the centuries. Lisbon is positively covered in this public eye candy, with azulejo-adorned buildings all around town depicting everything from elaborate historical scenes to something as simple as a street name. The best place to start looking is Museu Nacional do Azulejo.

Portugal is home to some of the world's best (and cheapest) wine. And Lisbon has a long list of intimate wine bars that do a phenomenal job pairing local juice with fantastic artisanal cheese and charcuterie boards, chosen by enthusiastic sommeliers who are particularly skilled at turning a bit of wine and cheese into a fantastic travel memory. If you hit just one bar, make it BA Wine Bar do Bairro Alto, but Wine Bar do Castelo and Lisbon Winery shouldn't be missed, either.

It's worth a trip to this unique rural tourism option in the pastoral hills just outside Mafra, where 18 ruined stone cottages of a 300-year-old village have been meticulously restored, down to the finest detail. What were once village wineries, barns, bakeries and homes are now cinematic countryside escapes – a rustic living museum that's as perfect as it gets for a romantic, wine-fuelled getaway from Lisbon's hustle and bustle. Toast to simpler times with a glass of port at sunset, shared with little more than a few roaming peacocks.

Having rocketed from sleepy fishing village to upscale beach resort, lovely Cascais, 27km west of Lisbon along the stunning Atlantic coastline known locally as A Linha, makes for a splendid city getaway. Flush with gorgeous urban beaches and even wilder surrounding ones, upmarket resorts and boutique hotels, travel-worthy restaurants (including the Michelin-starred Fortaleza do Guincho) and a bevy of excellent cultural attractions, it's no wonder it's a favourite relocation spot for expats. Throw in great surf, fun bars and a charming old town as well and you might just find yourself lingering a few days.