Back in the summer of 2016, my life was pretty great.  My bar had been open for about 6 months and was doing amazingly well; my marriage was at the top of its game; my alcoholism hadn’t fully taken hold yet and I was still living a life of freedom and (relative) normalcy.  And after over a year of our lives revolving around our business, especially the half where the bar was actually open and we worked 12+ hour days, every day, we decided it was time for a vacation.  August is the slowest month in New Orleans, after all, and if we didn’t get a little time away, we were probably going to die.

How we picked Puerto Rico, I can’t remember.  Maybe because it was exotic but easy?  No passport necessary?  They speak Spanish, and so do I?  But whatever the reason, our first trip post business opening was set for mid-August – I booked flights, bought a guide book, and after a tiny bit of research and recognizing that I didn’t have time to fully plan this trip in advance, I booked the first two nights at a nice hotel and a convertible mustang rental car and decided to leave the rest a la minute.  I probably thought I would plan more on the plane, or in those first couple days in San Juan, but that was not to be.  This would be a real adventure.

After a couple flights and checking into our posh beach hotel outside of town, we started to recover from the past few months, and we started to explore.  We went to Old San Juan and sought out some authentic food, from a little hole in the wall where not much English was available.  We hiked along a beach-side trail and drank water straight from the coconut.  We sat at beach bars and drank tropically boozy drinks and just stared out at the water, lost in the rhythm of the waves and the heat of the sun and the quiet.  We found stillness, and quiet, and peace.  It had been a long year.

After those first couple days, we had a week with nothing planned, to fly by the seat of our pants around the island in our insane bright orange convertible.  It really was a fun car to have for that week, even if it was a bit impractical and ridiculous.  Every evening, we would decide where we wanted to go the next day and spend the next night.  I would book the lodging, and we would sit at dinner pawing through my increasingly worn-out guidebook to plan the days adventures.  It was easily one of the best weeks of my life, and it has become the blueprint for many successful (and one very unsuccessful) vacations.  (You cannot do it this way in Cuba.  Just trust me, it’s too hard, you will wind up in tears of frustration and anxiety.  Make firm plans in advance or rue the day!)

One day we went ziplining, and then tried to find this rum distillery in the tiny town of Jayuya, way off the beaten path in the center of the island.  The GPS directions weren’t working, and no one in the town spoke English, and I learned the difference between “mopo” (mop) and “mapa” (map).  In the end, after speaking to two gentlemen drinking beers at the little tables in the back of the gas station (where I had been directed to find the mopo), they got in their car and actually led us to our destination.  It was amazing.  And then we got to the distillery, and still no one spoke English, so I had to translate the tour explanations!  I didn’t know my Spanish was so good until then, though it helped that Puerto Rico has a more Spain-Spanish accent (I struggle with central American dialects), and also I made up a lot of shit when I couldn’t understand, so that the lady wouldn’t know I didn’t understand.  “I don’t know what she just said, but I think it was something about those pipes,” I might have said quietly to my then-husband.

After that, we drove even further into the mountains, where we trekked through the rain to find that day’s accommodations – a wee little coffee plantation owned by a German ex-pat.  I should note that the roads in the middle of the country are quite narrow and windy.  And sometimes not in the best condition.  And possibly made of dirt in patches.  Anyway, we made it to the farm in the dark rainy night, definitely questioning our choice of vehicle.  But we had an amazing dinner in Ponce that night, and in the morning the sun was shining, the chickens were chickening, and we had the most spectacular freshly made breakfast and tour of the operation.  And some of the best coffee I’ve ever had to boot.

Then we really found our groove.  We ate obscene amounts of pork on Pork Highway – literally a stretch of road lined with lechoneras, shops roasting whole pigs with open air seating and often live music.  We stayed at an inn in Rincon where our back porch hung out over the open sea.  We hiked to an enormous waterfall where some brave dudes climbed to and dove off of the heights, surfacing in the calm pool below.  We went out of our way for unusual gelato flavors, and for a million tiny fishes in dough, and for a second trip to Pork Highway.  We stayed in a treehouse overlooking a mountain lake.  We went repelling and spelunking in a local cave.  

We took a tiny little prop plane puddle jump to Vieques island, where the wild horses roam, and where we paddled in bioluminescent bays full of dinoflagellates, and rode horses on beach (and in the sea a little bit) and hiked to lighthouses and black sand beaches.  And we just existed, slowed down and rested.  (We just happened to be there at the very end of August, mere days before the official tourist season ended and the island went into hibernation mode, so everything was still open but it was also very quiet and empty.)

And that was it.  We spent one more night in San Juan* before flying back to New Orleans and going back to the grind.  The end of what still lives in my memory as one of the best trips I’ve ever taken.  So why was it so great?  Why does it serve as a blueprint for a wonderful vacation to this day?  I think that there is an element of magic in these perfect memories, a je ne sais quoi piece of luck or the universe being in alignment or something.  But also, it was a trip where there were no wrong answers.  There wasn’t a checklist in my mind of the things we had to do.  We didn’t know what to expect, so there were no expectations getting in the way, ready to be unfulfilled.  We just relaxed and let it happen as it happened.  We were fully present and lived in the moment.  We had no preconceived notions of how the trip should be, so it got to just be whatever it was.  And thus, it was perfect.

*Side note because I’m a nerd and I just have to put this in here somewhere – originally, the Island was supposed to be called San Juan and the city Puerto Rico, which makes much more sense given that the city is a “rich port” city.  But that first European map maker fucked it up and reversed it, and the mistake stuck!

Below are the details I can come up with of the places we went on this trip. Please keep in mind that this trip was 8.5 years ago, so I am reconstructing from memories and pictures and the old guidebook that went with us. (Yes, I have kept every guidebook that I’ve ever owned.) I cannot tell you for sure what even still exists after so much time (and a pandemic, and eight hurricane seasons) but I know that they were all well worth the visit I paid them back then.

SAN JUAN AND AROUND

THE NORTH COAST

THE CENTRAL MOUNTAINS & PONCE

THE WEST COAST

VIEQUES ISLAND

• Esperanza – the town on the southern shore of the island, this is much more the touristic and ex-pat area and is a lovely place to hang out.
• Isabel Segunda – the other town, on the north side, holds the airport and ferry terminal, a nice lighthouse (Punta Mulas) and is filled with a much more local vibe. We had a great meal here at Bieke’s Bistro, a nice little spot with a menu chocked full of local seafood.