Punta Cana, A Work Retreat in the Caribbean (and My Ongoing War With Southwest)
My first time leaving the country for somewhere tropical, an all-inclusive work retreat on the white sand of Bávaro, where I finally met the coworkers I'd spent years working alongside, and confirmed my lasting opinion that Southwest is terrible.
The Dominican Republic was my first real tropical trip abroad, palm trees, turquoise water, the whole postcard. The catch? It was a work retreat, so paradise came with a to-do list.
Paradise, but make it a work trip
This was an all-inclusive resort trip out on the Bávaro coast of Punta Cana, the Dominican Republic’s flagship strip of big beachfront resorts on the island’s easternmost tip, where roughly twenty miles of palm-lined Caribbean beach just keeps going. It’s the definition of a relaxing place. And it was relaxing, except that it was also work. So there was this slightly surreal tension to the whole thing: you’re somewhere built entirely for switching off, but during the day you still had to, you know, work. Chill and not-chill at the same time. A weird but genuinely fun way to see the country for the first time.
The best part of the work angle: I finally got to meet my coworkers in person, the people I’d been working alongside for nearly three or four years by then. There’s something special about putting real faces and real laughs to names you’ve only known through a screen, and doing it on a beach in the Caribbean is not the worst way to do it.
They’d been an entirely virtual team to me until that point, names and voices on a screen, nothing more, so simply being in the same physical place, sharing meals and a beach with them, was the whole gift. That’s the thing I’ll remember most about the work side of it.
The beach itself
Bávaro Beach is the real draw of this stretch, powdery white sand, calm opaline water, palms leaning over all of it. Even on a working trip, that scenery does its job on you. The classic thing people do from here is the all-day boat trip out to Saona Island, with the shallow natural “pool” full of starfish, I don’t know that I had time for the full excursion given the work, but the resort coast alone was plenty of Caribbean for a first taste.
In the end I kept it simple and stayed around the resort, no big off-site excursion. My rhythm was lovely in its own quiet way: work during the day, then the beach every single evening. For the few days we were there (about four in all), I got to just sit on that sand night after night, watching the water. And the food at night was delicious, the genuine upside of an all-inclusive. For a first taste of somewhere this unique and original, it was a really fun way to do it.
A word about the flights
I have to register a formal complaint, because it became a theme of my life: I flew Southwest for at least part of this one, and it earned its reputation early, we sat on the runway for about an hour before leaving because they’d bungled their own schedule. I didn’t like Southwest much then, and it’s turned out to be a recurring pattern. I have come to believe, firmly and repeatedly, that Southwest is terrible (the Las Vegas trip years later only sealed it). This trip may well be where that conviction was born.
The takeaway
My first tropical trip abroad was a funny hybrid, half retreat, half job, but it gave me the Dominican Republic, a beach I won’t forget, and the rare gift of meeting longtime coworkers face to face. And it confirmed an airline grudge I’ve been nursing ever since. Worth it.