It doesn't seem right to compare Bordeaux, which dates from Roman times, with She's All That, the Freddie Prinze Jr movie in which the jock remakes the nerd into a prom queen.

So let's go classier and suggest the city, whose ornate 17th and 18th century architecture and wide waterfront have been hidden by decades of grime and decaying warehouses, is similar to the alluring bookstore proprietress in The Big Sleep who casts off her glasses and unpins her hair: "Hel-lo," responds Humphrey Bogart, lifting his glass to her. In the finest of traditions, Bordeaux has had a makeover.

The region is one of the most vaunted wine producers in France but until recently many of visitors gave the city itself a pass. Prostitutes and shady characters strolled its rundown waterfront, black grime obscured the architecture.

The experience was a little defeated. But a recent regeneration project, backed by mayor (and former French Prime Minister) Alain Juppe, has scoured buildings, turned the area by the Garonne River to a sweeping promenade with a shallow pool reflecting the Place de la Bourse and resurrected its graceful beauty.

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Even the sex shop I passed on the waterfront on the way to dinner was tucked into a delightful 18th-century carved limestone edifice, its neon sign glowing almost decorously in the night. A new whisper-quiet tram, free from overhead lines in the central city, whisks visitors and locals around its 35kms tracks (expanding to 45kms). On 28 June, 2007, it was named as a Unesco World Heritage Site.

Oenophiles may sputter into their vin rouge to hear it, but just making the rounds of Medoc, Margaux or Saint-Emilion isn’t the full Bordeaux experience anymore.

Within the city limits, there is the earthy terrine-like grenier medocain made of pig’s snout and ears to taste, chocolate from historic chocolatiers to be eaten, canelés – the traditional fluted cakes once made by nuns for the poor in the 1800s, now a bordelais standard – to learn about (“It must be crusty outside, but inside mellow, yellow,” describes my guide with intensity and passion. She also points outs a shop where I can get the traditional copper molds to make them affordably rather than paying a premium price at the ubiquitous chain Canelés Baillardran.)

This is one shortcut you won't want to miss to get the most from Bordeaux: enlisting the Bordeaux Tourist Office. It runs tours and walks every day of the week, taking in everything from the area's most famous wine regions to bike tours and monument tours by horse-drawn carriage.

The guides have overarching knowledge about the history and architecture and reveal unusual and interesting features of the city, such as the foodie tour which includes a visit to the renown local cheese shop in town that ages its wares in its own cave (Jean D’Alos). "The cave is from the old convent from the 11th century", my guide tossed over her shoulder as we walked in.)

Recently on a bright chilly Saturday autumn morning I waited at the tourist office with visitors from Japan, England and the US, for a walk around the old wine merchants district. Our guide, in a distinctive lime green puffy coat, lead us round the old wine merchants area, known as Les Chartrons.

Wine merchants, or négociants, had imposing buildings here, where they lived, ran the business, made wine and, in ground-floor cellars, aged their vintages. These days only the gorgeous houses, built on marshland, remain. Except for one. Calvert is the only wine house still operating in Les Chartrons. We toured the restored historic building and wine-making facilities and finished with a tasting in the cellar.

Then we wandered back, through streets whose design still mimics the cellars below them, coming across the La Fête du Vin Nouveau and de la brocante, a wine and flea market festival, where she pointed out a knickknack shop that's also a bar (see need to know).