I stare out the window of my friend's house in the once middle-class Vedado neighbourhood of Havana. A rusted 1956 Chevrolet Bel Air wheezes past, trailed by a beaten-up Soviet-era Lada taxi rattling over the potholes. The air smells sweetly of mimosa and, vaguely, of mildew. Jalousies creak on rusted hinges, as a cooling breeze sweeps in from the sea.

"I want to live here," I sigh.

"Why not marry Jessica?" says my friend, Mari, speaking of her teenage daughter. She doesn't appear to be joking. Cuba constantly delivers such curveballs. Whenever I'm in Havana, I feel like I'm living inside a romantic novel or a Hollywood thriller.

Mari's shocker sends me in search of a drink. I head to the nearby Hotel Nacional de Cuba for a mojito and cigar (like Che Guevara, I'm partial to Montecristos) on the terrace, where a five-piece band spices things up with sexy salsa. The landmark 1930s grand dame is still the preferred hotel for visiting bigwigs - Lucky Luciano famously held a mobster summit here in 1946, ostensibly to honour an up-and-coming singer named Frank Sinatra.

Gato Tuerto is down the hill, on Calle O, so I call in for some late night musica filin ("feeling" - meaning romantic - music). This tiny 50s supper club has been spruced up for tourists, but patrons are mostly Cubans and expats, and it still feels as though Sinatra and his Rat Pack might saunter in. The lights go down whenever someone orders an Orgasmo, the flambé house cocktail.

Gato Tuerto reflects one of Havana's unique enchantments: its aura of pre-revolution redux. Throughout the city, retro nightclubs, worse-for-war Detroit imports and grimy adverts for Hotpoint and Singer, soldered by tropical heat onto weathered façades, demand double-takes at every turn.

The next day, I hail a colectivo (shared taxi) - every visitor should do so - and jam in with six Cubans as the creaking circa-1948 Cadillac cruises down Avenida Linea to the rhythm of a rumba on the radio. My destination? El Cocinero, one of Havana's trendiest paladares (private restaurants). A spiral staircase corkscrewing up through a red-brick chimney spills me onto the chic rooftop, which has been conjured into a restaurant from a former cooking-oil factory by the visionary owners. I savour gazpacho, a goat cheese baguette and garlic octopus tapas al fresco, and observe the city's farandula (bohemian in-crowd) chat over cocktails before streaming downstairs to the adjoining Fabrica de Arte, a private avant-garde cultural venue that wouldn't be out of place in Hong Kong's SoHo. The night's fare is an acrobatic dance performance and erotic art expo.

Don't believe anyone who tells you Havana is sclerotic. Or, worse, that the food is boring. Chic clubs and paladares have blossomed since 2011, thanks to Raul Castro's economic reforms.

Most Cubans are too hard up to partake of Havana's new "middle class" spots, however. And so the city is best appreciated on their simple terms: at the farmer's markets, such as at calles 19 and F, displaying mini mountains of guayaba, maranon and other strange tropical fruits; the seafront Malecon promenade, where youths gather at night, gossiping and flirting over shared bottles of rum, impervious to the salt spray crashing over the seawall; or Parque Coppelia, where an ice cream can be enjoyed in the dappled shade of jaguey trees dropping their aerial roots to the ground. Cuba's rich diversity can be observed standing in line at Coppelia (supposedly the world's biggest ice creamery) on a sultry afternoon.

A walk down any Havana street provides a kaleidoscope of beguiling vignettes. Vedado's calles 17 and 19 are lined with beaux arts buildings such as the Museo de Artes Decorativas, lavishly embellished as if the pre-revolutionary countess owner were still there, and the mansion at calles 19 and H that houses the National Union of Writers and Artists of Cuba (UNEAC). Ground zero for intellectual life in Havana, UNEAC hosts regular penas - musical and literary gatherings - which are open to all.

The six-lane seafront Malecon boulevard sweeps along the Atlantic seashore, linking Vedado to colonial Habana Vieja ("Old Havana"). It offers a microcosm of Havana life: fishermen casting off on giant inner tubes; the shiftless selling cigars; musicians practising with guitars and trumpets. With a camera in hand, what should be a 30-minute stroll can take half a day, so many are the distractions.

Habana Vieja preserves one of the great historical cities of the New World. Castles, convents and palatial mansions dating back centuries still reign majestically over plazas and cobbled streets haunted by the bootsteps of conquistadores and, infamously, the ghost of Ernest Hemingway. A stone's throw from Plaza de la Catedral, with its exquisite 18th-century baroque cathedral, is Bodeguita del Medio, where Hemingway supposedly supped mojitos. The reality is he rarely drank there, but try telling that to the groupies that make a beeline for the venerable, graffiti-strewn bar.

Off the plaza's southwest corner, tucked into Callejon del Chorro, is Taller Experimental de Gráfica, a graphics cooperative where artists engrave and print one-of-a-kind pieces on antique, hand-primed presses. Adjoining the workshop is Dona Eutimia, one of the best paladares in which to enjoy down-home creole cooking, such as ropa vieja (braised lamb prepared with garlic, tomatoes, and spices) served with heaps of white rice and black beans.

A FEW WEEKS AFTER Mari's offer, I am back in Havana and pay her a visit.

To my relief, Mari tells me that she and her husband, Jorge, have reconsidered having me marry Jessica. Then she throws me another Cuban curveball: "Jorge and I can divorce and you can marry me."

I smile.