Along the rain-slicked cobbles of Lisbon, rows of delighted tourists are stopping at the sight of me. Some whip out their long lenses to get a close-up shot. A teenage boy almost falls over himself to thrust out an emphatic thumbs up. This lavish attention isn’t down to sudden film-star status. It’s my vehicle that’s causing commotion: an English Squire sidecar, trusty companion to a Moto Guzzi vintage motorbike – a temperamental Italian who announces its virile presence with an unapologetic roar. This is alternative Lisbon at its best; a thrilling ride through the city.

Astride this eye-catching 1930s hulk is Pedro, my guide from the Sidecar Touring Company. Sporting a bushy grey moustache and pointed yellow cravat, he looks like he knows a thing or two about vintage style. If you're thinking of visiting Portugal, get in touch - we can pair you with an experienced travel expert to plan a trip for you.

Life on three wheels

A twist on vintage sums up Portugal’s charismatic capital, where street art is revered as much as the oil-paintings that dwell in its cathedrals, liberal values are prized alongside long-held traditions and music drifts from outdoor cafes that seem to belong to a more gentile era. And as the city’s relaxed rhythm is best experienced at a rumbling pace, our old-fashioned double-act is a fitting way to see it and definitely one of the more unusual things to do in Lisbon.

Plus, Pedro rules the road, whistling to send pigeons flapping out of our way and beeping at pedestrians with similar effect. I grip the Squire’s sides as we accelerate onto the fast three-lane Avenida da Liberdade, whizzing past the regal Parque Eduardo VII. As we nudge into the Baixa (downtown), the evaporating rain intensifies the colours of blue-and-white azulejo tiled buildings.

I’m grateful for our three wheels. Built on seven hills (or eight according to some), these streets rise and fall and criss-cross and curve like a ball of tangled thread. I get the impression that if I tried to retrace my path on foot, I might discover it had morphed, Labyrinth-style, into something else anyway.

Alternative Libson - the author in sidecarThe author Siobhan in her trusty sidecar © Siobhan Warwicker

Exploring Chiado

Our first stop is the Chiado district, where Pedro takes my arm over the slippery tiles of Rua Garrett (each district in Lisbon has its own unique pattern on the mosaic pavements). We step into the dark-wood-panelled gloom of a long and narrow café, candelabra casting a glow over the waiters as they move deftly across the chequered floor.

When Café A Brasileira opened in 1905, it swiftly became the epicentre for a collective of writers, artists, and free-thinkers, who would gather and debate between sips of absinthe and bica (espresso). A bronze statue of Lisbon’s famous poet Fernando Pessoa, in his trademark fedora hat, ponders eternally outside. One of the most significant literary figures of the 20th century, Pessoa was a regular at the café, where he could be seen feverishly writing beneath a trail of cigarette smoke.

A Brasileira isn’t unique in its lingering heritage. At least 50 shops in Lisbon have been selling the same products, from the same venue, for more than a century. Fearful of those precious businesses being squeezed out, in 2016 the council introduced the Shops with a History initiative (Lojas com História), to prevent eviction and fund restoration of stores with cultural significance. Chiado is home to several long-standing stores, including Livraria Bertrand, the world’s oldest bookstore (est 1732), which rubs shoulders with the retro-fitted Barbearia Campos barbershop, in operation since 1886.

Shops and services aside, resilience has long been part of the fabric of Lisbon. This is a city that rose from the rubble, rebuilt almost from scratch after the devastating earthquake of 1st November 1755. An estimated 8.7 on the Richter scale, it resulted in around 60,000 deaths and shook the earth with such force it caused the water of Scottish lochs and Norwegian fjords to tremble.

One of the few surviving structures in Chiado from pre-earthquake days is the Carmo Convent, an imposing, cream-stone Gothic church that stands wistfully over Rossio Square and the Baixa below. Still missing its roof after it collapsed onto worshippers that fateful morning, it was left open to the stars to commemorate the dead.

Back in my sidecar, we judder through steep Bairro Alto to Cais do Sodre, damp air amplifying our engine’s growl behind the rattle of the yellow number 28 tram, packed with people like sardines in a tin can. Once a salty sailors’ quarter, good times are rooted in this playful district, as noisy wine bars spill outside onto Rua Rosa, the colourful main street.

Alfama's alternative charms

On to Lisbon’s oldest neighbourhood – the one area that survived the earthquake – rough-and-ready Alfama, where laundry from the shuttered apartments is strung high above live music bars and cavernous porches. It’s a squeeze for our Wallace and Gromit set-up. I hold my breath at the prospect of meeting a car head-on, knowing that if we are forced to reverse, Pedro must disembark and haul our hefty machine back by hand.

Luckily, Alfama is sleepy during the day, its residents having a reputation for nocturnal tendencies. As the birthplace of Fado, a mournful sort of local folk music, its distinctive culture is still celebrated nightly. Dancing, music and feasting into the early hours is an almost daily occurrence but reaches its peak during the annual sardine festival (Santo Antonio), which sees garlands strung up across the narrow streets and throngs of people dancing in the streets all night long.

Alternative Lisbon - Alfama districtAlfama's steep streets © David Evora Marquez/Shutterstock

Life on the river

Trading on seafood is just one way in which Lisbon has been shaped by its location on along the western edge of mainland Europe. Even before we reach it, the River Tagus seems omnipresent, the city’s hills and strange angles giving way to cinematic river views that often take me by surprise.

Cruising down the riverfront Avenida Brasilia, we peel off our jackets to enjoy the briny-tasting breeze as the sun tips into full beam. Within 10 minutes, the Unesco-listed 30m-tall Belem Tower appears at the lapping water’s edge. Built as a defence tower in the 16th century, it’s a monument to Portugal’s pioneering role in the Age of Discovery, when explorers would set sail from Belem to seek power and wealth in all corners of the Earth.

It’s in Belem that I find the biggest crowd of tourists yet. They are clutching dainty yellow pastries, topped with a dusting of cinnamon and sugar. The hub of the action is Pasteis de Belem, known as ‘home of the Portuguese custard tart’ since it opened in 1837, serving a secret recipe from the monastery next door. It’s popular for a reason – its tarts are delicious. Biting into my still-hot pastel de nata, the centre oozes as flakes of fresh pastry float to the floor. Thousands make this pastry pilgrimage each day; by the time the ovens are switched off, around 20,000 will have been sold.

More visitors than ever are tuning into Lisbon’s delights. They’ve brought with them a flux of hotels and by 2022, a new airport is due to open too. Policies of preservation such as Lonjas com Historia may not hold back the tide of change forever. But when I imagine Pedro zooming around on his days off, in his favourite Sixties Vespa – wife in a sidecar of course – I know the soul of the city will never change. Long live fun-loving, eccentric, alternative Lisbon.

Find places to stay in Lisbon

Half-day sidecar tour is included with a stay at the Four Seasons Hotel Ritz Lisbon when you book for three nights or more (from around £419 per night B&B).

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