The first time I heard about Punta del Este, a well-known luxury travel magazine referred to it as “the Hamptons of South America.” Also sometimes compared to ritzy beach destinations such as Monaco and St. Tropez, the city attracts a wealthy crowd during the southern hemisphere summer months. A high proportion of visitors are well-off Argentines from Buenos Aires, many of whom escape the city on their yachts. My interest was officially piqued.

Since my birthday falls in late January, I am always seeking warm weather getaways to celebrate. Coincidentally, my good friend Karen shares the same birthday with me, and we also share a close circle of mutual friends. It seemed preordained that we’d celebrate our 2020 birthdays together since I was still traveling full-time and Karen wanted to do get out of the U.S. and visit somewhere new. Did I mention it was Karen’s 40th?! Enter Punta del Este.

While it was difficult to convince a large number of our New York-based friends to join us for a birthday bash in southeastern Uruguay on a Tuesday night, we succeeded in bringing aboard our incredible travel-obsessed friend Lindsay. It helped that Lindsay was able to tie the trip in with some business meetings in Buenos Aires. Corporate travel for the win!

How We Got to Punta del Este from New York

I’ll admit, it was not easy for us to get to Punta del Este from the U.S. I could not find a direct route from any NYC airport to PDP (Punta del Este’s airport), and there was really only one or two daily flights from Buenos Aires. Given our various travel requirements (Lindsay’s meetings, Karen’s work schedule, my, well, nothing), I proposed that we meet in Buenos Aires for a couple nights, then take a quick fifty-five minute Aerolineas Argentinas flight to PDP in the afternoon. The plan worked out perfectly, especially since we were already in BA and the flights to Punta del Este operated out of AEP, the city’s local airport. (Read more about my BA recommendations here. For the record, if you wanted to skip BA and expedite your trip to Punta del Este, you could simply fly into EZE, then Uber to AEP.)

The AEP>PDP Aerolineas flight left a lot to be desired in terms of legroom, but at least it was less than an hour long
I also appreciated the views when flying out of AEP vs. EZE

Where We Stayed in Punta del Este

Most of the hotels in Punta del Este proper are beachside high rises complete with casinos, nightclubs, etc. There are also some boutique hotels and houses for rent, but none of these really aligned with our special birthday vision.

Then we found Hotel Fasano Punta del Este. Located inland about 40 minutes from PDP and 20 minutes from central Punta del Este, Fasano is a bit off the beaten path. But we fell for the laidback farm vibes juxtaposed with modern, high end architecture. The entire property was huge, featuring multiple restaurants, a pool, a gym, a river club, and more – yet it was still extremely private and uncrowded. It seemed like the majority of the commercial plans had yet to be realized, and we weren’t complaining. We rarely saw other guests or residents and loved riding around in a complimentary golf cart to explore the massive expanse of land available for our use.

Our room at Fasano Punta del Este
View from our terrace, overlooking some of the private villas available for purchase
Sunset view showcasing one of the property’s three restaurants

Fasano is a Brazilian brand, and I had stayed at the glamorous Hotel Fasano Rio de Janeiro during my first visit to Brazil. Both Fasano properties boasted impeccable modern design suited to the surrounding environment and incredible amenities (in particular, the rooftop pool at the Fasano in Rio is one of my favorite hotel pools in the world – read more about my time in Rio here).

The relaxing lower pool at Hotel Fasano Punta del Este – very different vibe than Hotel Fasano Rio, but still quite nice

While I had no complaints about the hospitality at Hotel Fasano Rio, unfortunately the service at the Punta del Este property left a little to be desired. After more time in Uruguay, I realized that this was most likely due to cultural differences, as the Uruguayans we met were all very laid-back and chilled out, and we experienced slow service nearly everywhere we went. The locals just didn’t understand that we New Yorkers were used to getting exactly what we asked for – immediately.

Enjoying aperitivo by one of the pools during our first night in Punta del Este.
Frighteningly, Lindsay and Karen almost got locked out overnight after going for a post-dinner swim – despite the fact that some staff members saw them going out to the pool. Fortunately, Lindsay had her phone and was able to call the front desk to let them back inside.
One more sunset view

What We Did in Punta del Este

We planned to spend three days in Punta del Este (Sunday-Wednesday), which gave us enough time to do everything we wanted, but I would probably recommend tacking on an extra day or two if you want to spend more time lounging by the pool or the beach. We decided to rent a car, which was expensive, but it was also expensive to take taxis (which we did a couple nights when we wanted to drink), and driving was required to explore the area. Basically, everything in Uruguay was expensive, especially for Latin America. Anyway, here’s everything we did during our visit, in chronological order:

Dinner at Locanda – The more casual of the two restaurants at Hotel Fasano, Locanda is in a relaxed setting overlooking the countryside and the Maldonado River that flows through the property.

The bar at Locanda
Enjoying some Fernet and Frangelico digestivos

Lunch at Bikini Beach – The stylish manager at Hotel Fasano recommended Bikini Beach to us, so we decided to start there on our first full day in Punta del Este. The restaurant/beach club was just okay, but it was on the beach and it did have a cute dog that came over to make friends with us. We also enjoyed exploring the small town (if you could call it that) of Manantiales up the street. There was some good shopping; I ended up buying two cover-ups at a Roller Rabbit shop.

Me with our new little friend at lunch

Seeing Los Dedos de Punta del Este – Admittedly, this sculpture of fingers reaching out from the sand on Playa Brava (“los dedos” translates to “the fingers”) is a tourist magnet, but we kept coming across pictures of the iconic and somewhat creepy sculpture when researching Punta del Este. We of course had to see it for ourselves.

We took this selfie while waiting in line for our “proper” shot with Los Dedos, which still included a bunch of random strangers
View of the skyscrapers along Playa Brava in Punta del Este

Drinks at Casapueblo – This hotel/art museum/restaurant/bar is located in Punta Ballena, about twenty minutes east of Punta del Este. Built by an Uruguayan artist in the late 1950s, the twisting, whitewashed structure is built into a steep hill, and immediately reminds one of Greece.

View looking down at the pool at Casapueblo

We unfortunately arrived too late to see the museum, but we were able to snag a table overlooking the sunset. The bar seemed to be popular with locals of all ages, and I delighted in watching both young kids and senior couples dancing to the live music as the sun went down.

Our corner table was the perfect vantage point for both the sunset and some heartwarming people-watching
Another beautiful sunset

Dinner at Virazón by the port – Back toward Playa Brava and Los Dedos, the port of Punta del Este is where much of the action happens in the evening, and we figured we had to go there at least once at night. We had Hotel Fasano make us a dinner reservation at Virazón, one of several well-regarded restaurants by the port, and we were seated at a table indoors by the window (it was extremely windy, so we couldn’t sit outside). Maybe it was because we were in a high-trafficked area, but the service at Virazón was among the best that we received throughout the entire trip. All the food was fresh and tasty (salad and fish for me). They even called us a cab to take us back to Hotel Fasano. Definitely recommend Virazón.

Birthday brunch – Our last day in Punta del Este was also Karen’s and my birthday! Despite my previous complaints about the service at Fasano Punta del Este, they did a great job going above and beyond, setting up a special brunch for us by the pool. Huge credit goes to Lindsay for secretly coordinating everything and following up with the hotel staff multiple times to ensure that everything went as planned.

Yep, that’s our birthday
Lindsay drove us in the golf cart to our “surprise”
Starting the day off right with poolside brunch, complete with mimosas
After brunch, we rode down to check out the River Club, where we were oddly the only guests

Drinks at El Chiringo Anastasio Beach Club – After brunch our plan was to head to Jose Ignacio, a relaxed beach town about thirty minutes east from Punta del Este, for a day of beach club-hopping. Our first stop was El Chiringo Anastasio, a laidback beach club with surfer vibes. We didn’t eat here, but the drinks were well-made and the service was decent. The scene wasn’t crowded, but it didn’t feel dead like Bikini Beach had.

It was windy on the beach, but we didn’t mind
Two Campari Spritzes and a rosé enjoying the beach view

Lunch at Parador La Huella – Next we had 3pm reservations at Parador La Huella, a short walk down the beach from El Chiringo Anastasio. Ranked #28 in the world on 2020’s World Best Restaurants list, Parador La Huella seemed like THE place to be in greater Punta del Este. The classy beach shack was packed with diners, the overwhelming majority of whom were Latin Americans.

We checked in with the hostess, then waited… and waited… and waited. We watched table after table getting seated before us, while the hostess continually assured us that our table would be ready soon as our impatience grew. I noticed another group of Americans also waiting for a long time and we started chatting with them. Fellow New Yorkers, we vented about the slow service and debated whether it was a coincidence that we were still waiting while groups of Latin Americans were seated before us. Was this discrimination?! I finally made my way inside to the bar to get a bottle of rosé for us to drink during the interminable wait. That helped, although I couldn’t help but think that if we were in NYC and waiting so long for a reservation, the restaurant would have offered to comp us drinks – at least.

Finally, our table was ready… a cool ninety minutes later(!) While the whole experience was rather annoying, we quickly forgot our frustration when we settled into our cozy outdoor table and ordered the restaurant’s signature grilled fish, alongside fresh veggies and, of course, more rosé. We also made friends with a cute Uruguayan family sitting next to us – a mother who looked way younger than she must have been, along with her two cute adult sons. Despite the unacceptably long delay in being seated, the food and ambiance at Parador La Huella did not disappoint. If I were to return, I would probably aim to get an earlier reservation to minimize delays at this crowded spot – and maybe try to go with some locals to see if that improves the service at all…

Finally seated at La Huella!

Drinks at Las Piedras Beach Club – Our final stop in Jose Ignacio was Las Piedras Beach Club, which is actually affiliated with Hotel Fasano in some way. A quick drive from Parador La Huella, the laidback beach bar had a luxe vibe, but was completely dead. We had the place to ourselves for the couple hours we were there. No problem, at least we had a prime view of the sunset.

Like so many of the places we visited in Punta del Este, we were the only guests at Las Piedras. No idea why!
We could make our own fun. Final sunset in Uruguay

Dinner at Fasano Restaurant – For our birthday and final night in Punta del Este, we decided to stay in and dine at Hotel Fasano’s highest end restaurant, the eponymous Fasano. Described as “regional Italian,” the meal was excellent, albeit pricey. They also gave us a cute mini chocolate cake with a candle as a birthday dessert.

Another successful birthday in the books

The next morning Karen and I had to wake up early to drive to the Montevideo airport and catch a flight to Santiago, Chile (the only options LATAM offered were in the late morning or early evening, and we were eager to start the Chile leg of our trip ASAP). Approximately a two hour drive through the Uruguayan countryside, we passed green pastures and a ton of cows (apparently, Uruguay has more cows than people). It was an easy ride, with well-maintained roads and very little traffic. In general, driving in Uruguay was very relaxed, and that was one area where I appreciated the laidback mentality of the country!

We had given ourselves plenty of time at the airport because we had to return the rental car, check in for our flight, and go through exit immigration. My previous experiences traveling via air throughout Latin America (and with LATAM) had often not been smooth, so I wanted to be sure we had a time buffer. After a minor delay trying to find the Hertz rental car office, we were pleasantly surprised by our experience at Montevideo’s Carrasco Airport. Checking in was a breeze, we sailed through immigration, and the lounge was nearly empty. Once we headed to the gate for our flight, we found some comfortable reclining seats that enabled us to watch the (very light) traffic on the tarmac while we waited to board. Carrasco was officially my favorite airport in Latin America.

So impressed with the Montevideo airport

My final musings on Punta del Este: while the chilled-out vibe and slow service sometimes drove us crazy, it was no different than the “island time” mentality of other beach destinations that don’t subscribe to the chaotic and rushed city lifestyle. The expansive stretches of beach combined with the vast green countryside offered some beautiful, calming landscapes. Uruguay in general felt very safe, especially compared to other places in Latin America. On the flip side, it was also by far the most expensive country I had visited in the region. So, it had its pros and cons, but definitely more pros, and I’d absolutely return. But next we were ready for a change of pace: Santiago and Valparaiso, Chile.