Like most men before getting hitched, I snatched defeat from the jaws of victory plenty of times, but few fails rival what transpired in 2006 when my friend Scot and I visited South Beach. I had arrived first and met two women visiting from Uruguay, and they agreed to meet us for drinks later that night at the Clevelander. The sharply dressed Uruguayan ladies arrived at the Art Deco bar shortly after we did.
“So, where are you from?” asked Scot, a bulky Chicago native with a tough-guy tone.
“From Uruguay,” said the first woman. “Do you know where that is?”
The correct answer should always be, “Yes, I hear it is a wonderful place.” That was not my friend’s response.
“No,” he said. “I don’t know any of the countries down in South Africa.”
“Ha! He’s kidding,” I stammered, my chuckle as unconvincing as a low-budget telenovela.
“Huh?” replied Scot, bemused.
The women exchanged a split-second glance before one of them remarked, “Actually, we stopped by to say we are not able to hang out tonight, but thank you for the invite.”
“No problem,” I said. As the ladies darted for Ocean Drive, I glared at Scott and said, “South Africa isn’t even a continent!”
“What you gonna do?” replied Scot with a nonchalant shrug.
With this exchange burnt into my frontal lobes, a call I received a month later almost seemed surreal.
“Hey Dave, you ever been to Uruguay?” asked my friend Eric. “Punta del Este is like the South American riviera, and I am going for New Year’s Eve. Are you interested?”
The Portlandia-raised Angeleno wanted a wingman who knew Chile from Chad, and I agreed to go, but the experience would show I apparently can’t tell Chloe from Chad. But we’ll get to that later.
Ibiza-style Punta del Este sits on a peninsula, but the Punta reference typically entails a stretch of coastline that extends 20 miles northeast past La Barra to Jose Ignacio, the poshest of the beachfront towns. The famed Bikini Beach sits on the outskirts of La Barra, and Lonely Planet said you must “tan it, wax it, buff it” before daring to step upon its fine sand. In decades past, this coastal strip reportedly hosted the likes of Che Guevara, Brigitte Bardot and the Rat Pack, and its current celebrity clientele led the travel press to dub Punta the St. Tropez of South America.
“If you want to get wild on the beach, the place to come is Punta del Este,” said host Natalia Cigliuti in a 2001 episode of Wild On E! filmed at Bikini Beach. Five years later, Punta had only become more festive, and New Year’s Eve in the middle of summer is the peak of high season.
After arriving in the capital city, Montevideo, we had to take a bus to Punta del Este. I sat next to a woman who also came down from Los Angeles for New Year’s Eve. “I won’t go to a nightclub unless we have a table and bottle service,” she said, as the beat-up bus rolled down the highway. The woman had spent New Year’s Eve here several times before, and she told me about the exclusive villa parties and luxury night clubs. Eric and I looked like thirtysomething backpackers who didn’t know the meaning of bottle service, so obviously no villa party invites were forthcoming.
Jetlagged and exhausted, we arrived in La Barra and quickly headed out for a drink at one of the waterfront bars. The beach, with DJs spinning dance music on the sand, was packed yet still manageable. As is often the case, the first day after a long flight is more low key, and we spent most of our time jumping from bar to bar. Day two, however, meant hitting the beaches and enjoying the South Atlantic, but what happened that morning is still very much up for debate.