48 Hours in San Juan, Puerto Rico!

This week we spent three nights in San Juan, Puerto Rico, finally making good on a trip we originally scheduled to take in spring 2020 but had to scrap because Covid hit. The purpose was to visit one of Teddy’s oldest friends, and someone I knew from high school as well, Caton Burwell, who moved to the city with his wife Lizzie and their four kids in 2018. Lizzie was raised in Puerto Rico before she went to boarding school, and when they decided they no longer wanted to be in Alexandria, VA, this was their choice. All four kids are now bilingual and settled in a house in town with friends and activities. 


We arrived on Wednesday evening from Orlando. We had spent the previous four nights and Easter with Teddy’s family in Vero Beach, FL. All the cousins and siblings and everyone came to town for the weekend, and we had fun swimming in the pool and ocean. James and I even peeled off for a wildlife pontoon ride through the Pelican Island Nature Reserve because he is studying birds this year. We saw dolphins and a tortoise and lots of birds, including the very endangered American Oystercatcher.


When we landed in San Juan, Caton picked us up in his beat up 4Runner. He, like Teddy, looks exactly like he did in high school. A beach-ified version: Linen button down, croakies, tan, mandals. The “Island Ted” version of Caton. We checked into our hotel, the AC Marriott in Condado — on the beach, about halfway between Caton’s neighborhood and Old San Juan — and met Caton and Lizzie for dinner down the street at Via Appia. 


They ordered their drink of choice — rum and tonic with lime — so we did too, then got some Italian food and caught up. They’re planning a big trip this summer to Spain, France and Morocco and had a lot of questions about packing and using travel agents. Four kids is….a lot. 


When we got back to the hotel, James told us he wanted a hotel minibar for his birthday. The smell of foreign surface cleaner — in our lobby, in our room — was so familiar. Reminds me of my years in France, and of course, all our travels. 


On our first full day we hit the breakfast buffet, which also came with all kinds of deja vu, and walked to the beach in front of our hotel to let the kids swim and play for a bit while we watched. The water is turquoise with mild waves, and the crowds weren’t really crowds. More like a smattering. Low-key and pleasant, which surprised me — I figured a beach in a city would be somehow unpleasant, but it was clean and if you didn’t look behind you to see tall buildings, you might not even realize you were even in a city. 


Lunch was nearby outside at Paulina Escanes, a higher end Mexican-influenced spot that served tacos and a souffle-ish cornbread specialty called Torte de Elote Escanes. The kids got to have Cokes. There’s been a movement lately in our family to “normalize” things that we once treated as forbidden — screen time, candy, Coke, even orange juice. We were starting to see that they were sneaking things and hoarding them, so our new approach is to remove the mystique. Sure, have a Coke, see if I care.


When school got out, we headed to Caton’s house (I went on foot, Willa, James and Teddy came in an Uber because they wanted to have some rooftop swim time after lunch). It’s a gated typical tropics house with tiles and white walls, small pool in the backyard. We met Natty (7), Annie (9) and Juliette (13) — their oldest, Church, is a 9th grader at boarding school and wasn’t there. We also met Skip the jack russell terrier, Gladys the housekeeper, busy chopping garlic and making rice for dinner, and Camilla, the graduate student babysitter they hired simply to have an extra driver around for all the after school activities. Again, lotta kids to manage. 


On the wall of the kitchen was a white board that helped the family stay organized and reminded everyone of a few key principles: “1) Be early (not on time), 2) take personal responsibility, and 3) protect the team (united front).”

Annie went off to ballet with Camilla, while the rest of us piled into Caton’s beat up 2009 minivan from back home and made the after school rounds — first to horseback riding, which for some reason they referred to simply as “Horse” (as in, we have to be at Horse by 4:50). Then we hit Natty’s baseball practice, which James joined while the rest of us left to walk down a nearby beach. James has come a long way since this time last year, when he suffered a sudden-onset phase of clinginess and anxiety that took us about 5-6 months of hard work to undo. We think it came about from some combination of Covid and this one time we lost him in Brooklyn for five interminable minutes). All the efforts paid off — he’d now he’s Mr. Independent and Autonomous. Such a relief. If anyone needs advice on the matter I can share what we did!


That night the kids all swam together in the pool, shrieking and screaming and having a blast. Natty couldn’t remember James’s name and kept shouting J names like “Jack” and, my favorite, “Jeffrey,” to get his attention. Then we ate dinner together outside — a kale salad, rice and beans and a beautiful filet of red snapper which Caton prepared on the grill. By 9 pm Caton was driving us home to our hotel.

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Friday morning, our second and last full day in town, I did something I loved doing in new cities: I went to a spin class. It turned out to be terrible in all the right ways — a homemade operation above a Starbucks with a resident cat and an instructor wearing a SoulCycle t-shirt. The music was 80s American hairband (not reggaeton, as I was hoping), and the crowd was a mix of housewives and 20somethings. I got in a good sweat, though, and added it to my list. 


Around 9:30 am we Uber’d to Old San Juan, which took about 10 minutes. There are two 16th century forts in town — El Morro and San Cristobal — and we started at the former and walked to the latter, making stops along the way through the old quarter. It felt like a more spiffed-up and maintained — Americanized? — version of Cartagena. Parts of it even made us think of Valparaiso, but only because of the colors and the street art, not because it was crumbling like Valpo. It was not crowded at all, and Caton said we must have caught it between cruise ship stops.


The kids started whining, so we stopped at a bead shop. Willa spent 20 minutes designing her own necklace and James asked the shop lady if it was possible to make a bracelet he found smaller to fit his wrist. She removed some beads and rewired it to be a custom fit. Then we got smoothies. Gotta have some stops in there to break up the whining and recharge. 


Lunch was back out near Caton’s at Uno, a beachside restaurant with tables in the sand. Run by some Americans, popular with tourists and locals alike. According to Caton, Puerto Ricans are on “joke time” on Fridays, treating the day like year-round summer Fridays. They’re even known as “Viernes Sociale,” he told us (social Fridays). He and Lizzie joined for nachos, ceviche and samosas. They had brought their huge wagon of beach gear — boogie boards, paddle ball, chairs, cooler, etc. — and we posted up under some palm trees for about two hours. 


Between Florida and Puerto Rico, the kids have reacquainted themselves with/grown really comfortable again with ocean swimming. Diving in waves, riding waves, etc. Glad to see it. They got gelato and we watched people learning how to kite surfer, with Caton giving an expert play by play (see how she’s turning into the wind/tacking left/etc.). Skip the jack russell was there with us.


We had to get up and go, though, because Caton promised a local Domenican baseball coach in his neighborhood that Teddy would come by and give his high school guys some pitching instruction. This, we all had to see. Most of our crew walked to the ballfields near Caton’s place, which were in a housing project on the beach. Teddy and his high school Spanish (with translation help as needed from Caton and Lizzie), proceeded to spend an hour showing half a dozen gawky Puerto Rican teenagers how to fine tune their windups and fastballs. Willa and Annie went off to play on a playground while Natty and James played catch. It was awesome.


That night the four grownups went for a nice dinner out at Vianda while the kids stayed home with Camilla the grad student babysitter. Again, six months ago, this would not have flown with James. Now, I had to say “James!” four times to even get his attention to say bye as I was walking out the door. He just wanted to play with his new buddies. 


Dinner was proof that when it comes to catching up with old friends you haven’t seen in a while, you really need three meals together to cover all the ground and get past the pleasantries. How many times have you gone out to eat with old friends and left saying, “We didn’t even get to talk about XYZ!” or “There’s so much more I wanted to tell you/hear about!” A nice prolongued visit like this meant a satisfying catchup and reconnection. We have prioritized these since returning from our travels and made good on our promise to make them happen regularly. 


Now we are flying home feeling like we got a nice long visit to a cool and intriguing part of the world. Here’s what I wrote about it on Instagram: 


This week we visited San Juan, Puerto Rico to see friends from DC who relocated to the city in 2018. It was a trip we’d originally booked for spring 2020, but, like so many other people, had to scrap because of Covid. We were so glad to finally cash in our raincheck. It was a short trip, but we still got to tag along with our friends’ daily operation (minivan dropoffs to after-school activities, meals at neighborhood spots, walking the dog), as well as peel off to see the historic old quarter and learn about pirates and Ponce de Leon. In the Stories you’ll see Willa buying ice cream, James crashing baseball practice, Margaret trying a spin class and Teddy giving some neighborhood ballplayers pitching tips. It was a reminder that while we do punctuate our travels with sightseeing highlights, our favorite way to experience a place is by checking out everyday life and talking to and meeting the people who live in town. To those intrigued: San Juan is about as easy as it gets for east coast American travelers looking to feel far from home…English is an official language, no passport needed, USD is the currency, a direct flight is 4 hours from NYC, tourist infrastructure is well established, people are welcoming and kind, good mix of history/exploration and beach relaxation. Go see for yourself!