We saved the best part of our South American trip for last– the beaches of Uruguay.

We spent the final eight days and seven nights of the 3-week trip driving along the coast of Uruguay. After a hectic schedule in Peru and a week of late nights in Buenos Aires, it was time for some laid-back days, spectacular views, fresh seafood, and an open-ended schedule full of possibilities. For me this spells roadtrip. The beaches of Uruguay are perfect for a roadtrip. The entire coast from Colonia, Uruguay to the border with Brazil is only 300 miles long. I may be yearning for a roadtrip, but if the sun is shining and the beaches of Uruguay are calling I don't want to drive more than a few hours a day. Some days I might not want to drive at all.

Piriápolis, Punta del Este, José Ignacio, La Predera, Cabo Polonia, or Punta del Diablo? Crashing waves, miles of sand dunes, or rocky shoreline? Fishing villages, blazing hot nightlife, or lonely lighthouses? The entire coast, and all the beaches of Uruguay are beautiful. I researched them thoroughly before we left. Still, we couldn't decide exactly where we wanted to go and how we wanted to spend our time. As a compromise, we only booked one place to stay for the middle two of the eight days of our roadtrip.

I know this type of travel can be stressful for a lot of people. It's a bit worrisome to get into your car in the morning, drive haphazardly through a country you've never been to, where you don't speak the language and don't know where you're going to stay every night. However, for me this type of travel always reaps the greatest rewards.

In my experience, when you book too much of your trip ahead of time you usually end up in (over-priced) generic resorts that frankly could be anywhere in the world. Sure, they're clean and respectable and you're guaranteed to get a meal that's palatable. What you rarely get however, is a completely authentic experience.

lighthouse

There are drawbacks to this type of travel. There's always the chance you'll end up at a fleabag in some dump of a town. I'll admit that's happened to me before. Still, I consider that to be part of the adventure. To limit the chances of this happening, I've adopted a rule from my good friend Liz (the most intrepid traveler I know). She follows what we've come to call the 4-O'Clock Rule. Which simply says: whenever you're on a roadtrip with no specific plans, you start looking for a place to stay at 4-o'clock each day. It doesn't matter what you're doing or how much fun you're having– you must start the search by 4pm. Inevitably it will take hours to find a suitable place to stay. Because no matter how much research you do, or how lax your standards of acceptable luxury are, the first few places will just not work out. Maybe they're all booked up, or maybe the sheets stink. There could be issues with the plumbing, or perhaps the guy at check-in just gives you the creeps. There are a multitude of reasons to just say no to the first accommodations you come across. I guarantee if you start looking for a hotel after 4pm, it will be well after dark by the time you find a place to lay your head for the evening.

The 4-O'Clock Rule was particularly useful on this trip as we were visiting during the chicest, most fashionable two weeks of the high season in Uruguay. Which meant we were competing with models from Brazil, soap stars from Argentina and a few of the wealthiest jet-setters in the world for a decent place to stay. Of course, I knew how popular the beaches of Uruguay were going into the trip, but I was just not prepared for the throngs of beautiful people we encountered.

The pretty people of Uruguay

The Beaches of Uruguay

As this was a roadtrip, we opted to take the longer coastal road along Ruta 1 in order to see as many of the beaches of Uruguay as possible. It's an easy to navigate, paved highway, so we sailed through the beaches of Shangrilá, Logomar, Solymar and El Pinar. They were pretty, but far too close to the capital city of Montevideo for our purposes.

Atlántida, was our first stop. It's a bit more laid back, and less monied than some of the other areas we visited. Reminding me a bit of party-hard Rosarito, Mexico. So I thought a room there would be easy to snag. I was wrong. Fortunately it was barely 4pm and we still had hours to search before panic set in.

Next stop Piriápolis. Imagine Miami Beach, St. Tropez, and Ipanema all rolled into one old-school Mediterranean-style, balustrade-lined promenade. There were so many tanned, waxed, buffed, bikini-clad boys and girls plopped on the beach that I swear you could walk from beach towel to beach towel without ever touching the sand. Needless to say, the grand old Belle Epoque-style Argentine Hotel (with its sentry of winged-lions, heated river-water pools, casino, and summertime ice-skating rink), as well as every other hotel we stopped by nearly laughed in our face when we inquired about a room for the night. As I said this was the highest of the high season.

Piriáplois, Uruguay in the summerGrand Old HotelKen Eskenazi in UruguayWe had a better luck (thanks to the geo-tracking feature on Booking.com) at a quiet beach in the Ocean Park area of Puenta del Este. We snagged the last beachside cabin at Cabañas del Este just before sunset. Our first evening along the beaches of Uruguay was spent laying in the sand dunes watching the Milky Way, while drinking cans of beer and eating sandwiches we made with supplies from the nearby mercado– we couldn't bring ourselves to drive too far away from this remote little beach.

You can't talk about the beaches of Uruguay without bringing up Punta del Este (simply referred to as Punta).

In the 1950's Uruguay (and its hush-hush banking regulations) was the Switzerland of South America. A booming economy and gorgeous beaches allowed Punta del Este to compete with Havana and San Juan as the bon vivant's favorite Latin American summertime destination. However, a dictatorship and subsequent economic woes left the area mostly forgotten by the beautiful people it once beckoned. The political and economic changes in the last decade have helped Punta lure the world back to its beaches. It seems the jet-set hedonists, with their diablo-may-care attitude, are leading the pack.

In the winter Punta del Este is home to about 10,000 people. During the summer, the population swells to around 150,000. This tells you something about the area and its amazing comeback, because Punta itself is relatively small– confined to a narrow peninsula that divides the Rio de la Plata from the Atlantic Ocean. It's also the place where the coast of Uruguay makes a sharp turn and begins to run north-and-south as opposed to east-and-west. Meaning there are two styles of beach. On the Atlantic side is Playa Brava. It's wild, with raucous waves that attract a young surfy-set. Whereas Playa Mansa is calmer and better-suited to swimmers, and those who want to show off their (water-proof) Rolexes. Miami Beach-style high-rise condos and hotels, as well as the bars and restaurants that fuel Punta's all-night parties, act as a glittering backdrop.

Punte Del Este

It was tempting to spend the night along the main drag of Punta Del Este. But the high energy, glamor-seeking crowds, as well as the thought of another Buenos Aires style night of thump-thumping dance beats convinced us to carry on with our roadtrip. I also have to admit I was saddened by the graffiti defacing the hand in the sand monument at Playa Brava. This sculpture from Chilean artist Mario Irarrázabal has come to define Punta Del Este. I was sorry to see the strong visual statement (known as Hombre Emergiendo a la Vida - Man Emerging into Life) so poorly appreciated. Hopefully the marring of this impressive piece of art is temporary– but we didn't stick around to find out.

PunteDelEsteHand

Instead we chose to cross the roller-coaster bridge into La Barra. When talking about the beaches of Uruguay, I suppose you'd call La Barra a slightly sleepier suburb of Punta. It's just to the north and has shops full of beachware, home furnishings, antiques and other luxe oddities, as well as hotels at all price points, and several good restaurants. As with Punta there are two choices of beach. You'll find quiet water at the mouth of the lagoon, and more waves on the Atlantic.

The road into La Barra is lined with bars and restaurants that attract flashy cars and trendsetters. From great ice cream (Freddo), to a modern cafe with a view (FLO Cafe and Bar), to dancing in the sand at Crobar, there are many great choices here for nightlife. However, with a little more work and a set of wheels you'll find far better dining options in the more rural, wooded area along the lagoon. We enjoyed a wonderful meal and a tour of the chef's subterranean wine cellar at Al Forno. We had pizza from the wood-fired oven, slices of smoke-charred lamb, and fresh fish baked with vegetables in a cast iron box. We also enjoyed creative Pisco cocktails in a beautiful patio setting (as well as lively conversation with our super friendly hostess) at the nearby Peruvian restaurant Nuna.

La Barra, Uruguay

From La Barra we concentrated on day jaunts into the wine country of Garzón and the not for the faint of wallet José Ignacio ('Nacio to those in the know). I'll admit 'Nacio is my kind of beach town and one of my favorite beaches of Uruguay. It has a casual, feet in the sand elegance, not unlike Martha's Vineyard or parts of the Hamptons. However, with rooms at Casa Suaya and Playa Vik fetching 4-figures a night, we opted to see the sights without hitting the hay.

Jose IgnacioJose IgnacioThe other reason we decided to leave this beautiful section of the beaches of Uruguay behind was because it was time to check into the only accommodations we booked in advance. We had two nights at Posado San Antonio and we wanted to get checked in and onto its stretch of endless beach as soon as possible.

The chic, but rustic four-room guesthouse is located down and around (and over and through) several dirt roads. You'll bounce past fields of hay and cattle ranches and soon realize you're deep in gaucho country. Posado San Antonio may not be far from the (semi) busy road of Ruta 10, but it's a world away from most places you've ever been.

The posada is situated in a cluster of beach houses that range from decrepit looking, thatched lean-to sheds to modern masterpieces of architecture. Each sitting on large parcels of land, most with views to the sea. Privacy is not issue in San Antonio. I read that this stretch of beach is favored by Argentine movie stars because it still has the kind of isolation that's just not possible in Punta or 'Nacio anymore. In fact I probably shared sunscreen with one of them without even knowing it. Which is, I guess, the point of San Antonio from their perspective.

Ken Eskenazi, Uruguay

The posada itself is a simple structure with a lot of style. The current owner renovated it from a large carpentry barn, into four two-storied suites with a communal great room and kitchen where guests can mingle and dine. The outside patio looks over a pool fashioned from a giant metal tank. Just another example of the rustic charm of Posado San Antonio.

Posada San AntonioPosada San Antonio

I could have spent more time at Posada San Antonio. In fact we were tempted to stay on for the final three days of the trip. But the weather wasn't co-operating (our car got stuck in the mud during a came out of nowhere rainstorm– don't ask). So we decided to check into Hotel Las Brisas in town. Town in this part of the world is La Pedrera.

La Pedrera is a seaside village located in a rural area of eastern Uruguay known as La Rocha. It may well be the next bohemian-chic hideaway. The beaches of Uruguay come cheaper here (for now) and their entertainments are more relaxed than Punta and environs. The town is stunning in a simple sort of way. The beaches of Uruguay here, are as good as they get. The bluffs lining these beaches are dotted with a sturdy, but beautiful style of adobe brick home– with thick walls and shutters built to withstand the elements. It has long been a tourist mecca, but the type of tourist is changing as the beaches of Uruguay get rediscovered.

La Predrera

Traditionally La Pedrera has attracted dread-locked backpackers, surfers and nature lovers. It's still attracts this crowd, but these days the hippies are learning to mingle with travelers like me. Because we're all looking for a type of simple authenticity that's becoming quite rare as the homogenized world embraces the pure-luxury, all-inclusive vacation.

La Predrera, Uruguay

None of that has happened quite yet in La Pedrera. The street here closes down to traffic after 8pm. That's when pedestrians ramble up and down the cobblestones, ducking into sidewalk eateries while drinking cheap beer from liter bottles or sipping hot Maté through a silver straw. Puppeteers, musicians, and artisans set up make-shift stands– creating a boisterous scene full of music and light. It was fun to watch La Pedrera's main street fill to full each evening with lusty-eyed teenagers hanging out in board shorts and bikinis, calculating each others every move. It's a mating dance I recognize from my own youth.

But as I said, for all this youthful activity La Pedrera is quite small, and still accessible to all of us. Walk a half a block in either direction and the the lust, laughter and lights are replaced by the smooth sound of the ocean, and the twinkling glimmer of Orion (standing on his head, from this American's perspective). All in all it's quite a special place. GREG

Greg Henry (Sippity Sup) in UruguayBeaches of Uruguay