I’m going to be famous. It won’t take long. “Half a day with me and you’ll be Lisbon’s main attraction,” promises our guide, Daniel. Hard to imagine given the city’s faded imperial beauty: its tumbledown tiled buildings, cobblestones and baroque churches, topped off with a grand castle. I buckle my helmet and swing one leg over my shiny black ride, bum landing with a thwack. My mortified friend sinks lower into her seat.

In a world of ever more zany city tours – St Petersburg’s roof climbs, LA’s celebrity-spotting jogs, Copenhagen’s Segways – Lisbon’s motorcycle and sidecar is the pick of the crop. One of the first urban sightseeing excursions, it remains a brilliantly practical way of taking in the seven steep hills of this joyfully inexpensive city pegged by gourmands as the next epicurean hotspot.

Keen to check out the architectural wonders, flurry of new eateries and rumours of €5-a-litre caipirinhas, we’ve chosen this vintage Russian transport over the yellow open-top tourist bus, rickety No.28 tram and vertiginous, knackering walks.

I’m perched on the back, my friend Alex is in the sidecar. A twist of throttle and we’re bumping across the cobbles of the Alfama district, the spotlight finding us at speed. Locals stop and stare, and a group of sniggering teens point and take pictures. I wave. Alex’s helmet slips over her eyes. We’re not dignified but we are famous.

Heads lolling, boobs bouncing, we zoom through the warren of narrow streets, ducking underneath washing lines of floral granny undies as we hurtle up to the medieval São Jorge castle. The combination of Moorish historical fortress, catapult (the souvenir shops are top notch in Lisbon) and 1940s motorbike makes me feel like a female Indiana Jones.

Alex instantly punctures the illusion: “We look like the Two Fat Ladies.”

Thankfully, where we fail, Daniel triumphs. Our effortlessly cool tour rider has got the nonchalant explorer look down to a T. Kitted out in Ray-Bans and a leather jacket, he’s both relaxed dude and expert guide, lacing historical facts and anecdotes with witty jokes.

We remount, take in a few miradors, and cruise downtown to Chiado, pulling up at the roofless Carmo Church and Covent. A striking but eerie site, the fallen ceiling of the structure is a stark reminder of the 1755 earthquake that flattened much of Lisbon. Today the sunshine floods through the open roof. The peaceful setting also marks the location of the Carnation Revolution of 1974, when a group of young idealistic army officers and flare-wearing youths spearheaded the downfall of 
Prime Minister Marcelo Caetano and the authoritarian Estado Novo regime.

The convent is just one side of the city’s history. Sunglasses on, the pace picks up on the open road to Belem, with a brief pit stop at the Belem Tower to marvel at Lisbon’s best example of sumptuous 16th-century Manueline architecture – its ship-like silhouette was designed as a decoy to pirates on the Atlantic. Further up the road we stroll around the handsome Jerónimos Monastery, another staggering symbol of crazy gothic Manueline design and the riches of European colonialism. It’s hard to drag our eyes from the intricate detail, but the equally outstanding, if more understated, Pasteis de Belem bakery beckons.

Floored by the aroma of coffee, cinnamon and custard tarts, we rest in the maze of blue-tiled rooms, faces sprinkled in flaky pastry as we munch through plates of pasteis de nata. The bakery echoes with the natter of old dears who’ve come for a catch up, leaving hours later with a day’s worth of gossip and boxes of pastries piled higher than their heads. With sales of up to 20,000 heavenly parcels a day, it’s a delicious conveyer belt of Lisbon’s finest tarts. You won’t regret getting in the queue.

Giddied by sugar and with our sightseeing tour coming to an end, we’re dropped off by Daniel at the River Tagus. Now we get to explore independently. And inconspicuously. Map in hand, we clamber our way up the hills of Bairro Alto, and ride the Elevador da Gloria funicular back down (in hindsight it makes more sense to do this the other way round). It turns out that Lisbon is enjoyably, although calf-quaveringly, walkable, and the civilised wrought iron kiosks (there are countless in the city) make handy rest points for an Alentejo ham sandwich and a refreshing Sagres beer.

It’s the first Sagres of many, and the drinking continues that night as we check out the other important sites of Lisbon. After a brief dalliance with fado – Lisbon’s signature sorrowful music – it’s on to the upbeat pulse of hip and happening Bairro Alto, which we fondly rename ‘Bally Ally’ after one too many. Here in the backstreets of the city, the narrow roads are packed with bars serving 50c beers and litres of caipirinhas. The rumours are true. Your hangover awaits.

Embracing the electric festival atmosphere, Lisbon’s residents spill out onto the pavements until the early hours. Laughter mingles with bands treating revellers to impromptu kerbside jams. In this part of town it really doesn’t matter which bars you go to, which is handy, because I can’t remember any names.

After a night on the turquoise tiles, the Cascais beach is our place to recuperate. 30 minutes by train from the city centre, the small town has several pretty coves to choose from. Bleary eyed, we soak up the sun and take a dip in the bracing water, keeping one eye on the sea view and another on the preening pro footballers tensing their abs and posing for selfies.

It’s hard to imagine them stuffing down custard tarts, or riding in a sidecar, gelled hair blasted by the breeze. But who cares? The motorbike and sidecar's a glorious way to start your sightseeing in a city that’s hugely generous with its charms. It’s the vain footballers’ loss. And our win.

Lisbon Food Tour

Conquering Lisbon one dish at a time, we take a gourmet walking tour with Celia, a food journalist and founder of Eat Drink Walk. She knows Portugal’s food scene inside out, and shows us the best spots for 10am cherry brandy, 12pm wine and a mid-afternoon port. Don’t fret, though, you eat enough of the city’s delicacies to soak it all up, including tempura beans, salty pork sandwiches and, naturally, custard tarts. Prices start from €69 for a half day tour, including copious amounts of food and drink. eatportugal.net

Pensao Amor

The queues can be hefty at this cool bar, but for good reason. Formerly a brothel (the location was handy for sailors docking on the River Tagus), the 18th-century historical building now has mirrored walls, frescoed ceilings and knockout cocktails. It demands a visit purely for the bathroom, where the walls are covered with X-rated ornaments. It’s on Rua Nova do Carvalho, Lisbon’s liveliest street once Bairro Alto starts to calm at night.

Cervejaria Ramiro

If seafood is your thing then dining at Ramiro – the ‘seafood temple’ – is a compulsory activity. Efficient waiters charge around the loud and lively Lisbon institution, doling out platters of the day’s catch, from salty percebes (the coastline’s famous barnacles) to crab. As my friend slips into a food coma, I squeeze in a prego – a garlicky steak sandwich some locals choose to finish a meal with instead of dessert. Avenida Almirante Reis 1, cervejariaramiro.pt

Memmo Alfama Hotel

Tucked down a side street in Alfama, this chic hotel is a minimalist’s dream. The alfresco terrace is a winner: by day we lounge by the pool watching the ships docking on the river. At night the terrace is sultry, with twinkly views over rooftops. Doubles from £100 a night including breakfast. memmoalfama.com

LX Boutique Hotel

A seriously peachy accommodation option, where Lisboa-themed feature walls collide with turquoise zings, and the trendy staff (square glasses and wrinkle-free skin) lay on complimentary wine and sushi for guests. The location in Cais do Sodré is ideal for those keen to sample the city’s nightlife. Scramble up the slope for the good-time vibes of Bairro Alto, then roll back down the hill to your cosy bed. We rise early, throw open the white wooden shutters, and make the most of the indulgent breakfast complete with deliciously decadent Portugese pastries. Doubles from £63 a night, including breakfast. lxboutiquehotel.com

EasyJet flies to Lisbon from five UK airports, starting at £34.99 one way. easyjet.com