Passport: Costa del Sol

Two major sites, both incomparable, explain Ronda’s rise on the travel radar. The first is the steep gorge, El Tajo, that slices the city in two. The 390-foot canyon is spanned by three ancient bridges, the Puente Romano, the Puente Viejo, and the most famous and most spectacular, the towering Puente Nuevo, one of Spain’s most photographed structures. Adjacent to the bridge on its north side is the Parador de Ronda, built inside the town’s former city hall. The Parador’s highly acclaimed restaurant is the perfect place for an excellent meal and breathtaking Ronda views.

Ronda’s other main attraction is its historic bullring, officially known as Real Maestranza de Caballeria de Ronda. Regarded by most as Spain’s (and the world’s) first official bullfighting ring, the Real Maestranza offers guided historical tours, and also houses a bullfighting museum. Each year in early September, the bullring hosts the pomp-and-pageantry-filled main event of Ronda’s weeklong Feria Goyesca celebration. The ring and Ronda itself once captivated the likes of Ernest Hemingway and Orson Welles, and in a gayer bit of lore, Madonna came here in 1994 to shoot the bullfighting scenes for her “Take A Bow” video (she was denied access by Real Maestranza de Caballeria de Ronda officials).

Still a small town at heart, Ronda doesn’t offer much in the way of overt gay life. It does, however, have a mile-long pedestrian shopping street called Calle Vicente Espinel, which boasts an outlet of Springfield, a sort of Spanish H&M with nice modern urbanwear at sometimes shockingly low prices.

To round out your Ronda experience, stop in at Finca Descalzos Viejos, a fantastic small winery in a converted early 16th-century monastery just outside the city center. As charming owner Flavio Salesi pours you a glass of one of his superb wines and you look out over the exquisite vineyards below, it’s easy to see how being a Descalzo Viejo (or Old Barefoot One) here centuries back wouldn’t have been such a bad thing at all. In fact still today, whether viejo or joven, there just aren’t a whole lot of things better in this world than being descalzo on the Costa del Sol.

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Passport: Costa del Sol