Malaga, Spain
Credit: Getty Images

Malaga, Spain

Malaga has served as the gateway to the Costa del Sol, Spain's sun-kissed seaboard, for 2,800 years. Much has changed – a portion of the seaside strip has been blitzed by cookie-cutter condominiums – but this Phoenician outpost has retained the jaunty Mediterranean appeal that once attracted stars like Brando and Sinatra to its busy tapas cafés and beaches crowded with beautiful women.

Buttressed between the mountain range with which it shares a name and a marina lined with massive yachts, Malaga is probably best known for the Alcazaba, a 14th-century Moorish citadel with a panoramic view of terra-cotta roofs spreading over the old town. The intricately decorated premises are almost as impressive as the view and thoughtful landscaping. A trek down the hill lie the exquisite ruins of a roman theater – discovered in 1951 during renovations to the city library. That was both big news and par for the course. One of the oldest continuously inhabited cities on Earth, Malaga is under perpetual excavation. Orange signs here tend to indicate archaeology, not road work.

Mere yards from the ruins, there's an homage to Malaga's most celebrated son, Pablo Picasso (Antonio Banderas comes in a rather distant second). Both the Museo Picasso and the nearby Museo Casa Natal, where the great painter was born, showcase the salubrious surroundings where Picasso developed his aesthetic during the late 19th century as Spain lurched towards modernity.

Also in Malaga's punchy portfolio, the new Museo Automovilistico. Home to one of Europe's finest vintage-car collections, the museo is built inside a striking 1920s tobacco factory where its exhibits are parked in a quasi-chronological starting grid. Belle Époque carriage wagons sit a few rows away from Bond-era Aston Martins and a Rolls-Royce Silver Spirit pimped out with Swarovski crystals. History buffs can also salivate over some more infamous models, including the 1939 Packard 12 made famous by FDR to a disconcertingly mint Mercedes 540K commissioned for the leaders of Nazi Germany.

But the city is more than the total of its museums and monuments. Post siesta, los Malagueños emerge onto their city's marble esplanades and make a beeline for one of town's bustling bodegas. El Pimpi, a one-time convent turned raucous wine cellar, is one of Malaga's most iconic haunts. Copas of fortified muscatel are paired with queso de oveja (sheep's cheese) and revered jamón ibérico de belotta – a sublime cured ham produced from free-roaming pigs who gorge on wild acorns.

Then the flamenco dancers come out in force and the evening begins in earnest. This city can go from zero to olé in a matter of seconds.

More information: Both Iberia and American Airlines fly to Malaga (via Madrid), while Delta operates direct flights from JFK in peak season. Amid the array of hotels and haciendas, check in to $125-a-night Molina Lario, a four-star hotel created from two revamped 19th-century townhouses featuring a killer rooftop pool-lounge. Don’t forget that Malaga also makes a super springboard for some passport-stamping trips to nearby Gibraltar and Morocco.