This year is a milestone anniversary for Virginia and me, and she spent most of the past year planning a trip to Indonesia and Singapore — part beach time and quiet, part city life and amazing food. And then COVID-19 happened and everything changed. Certainly bigger concerns than our vacation loomed, but we wanted to try to celebrate somehow. After canceling our existing flight, hotel, and restaurant reservations, we decided to try for a week in Puerto Rico — it offered beaches, good food, and domestic travel for simplicity.
Saturday
We were up very early for breakfast at home as we didn’t want to spend much time in the lounge and weren’t planning on getting food on the flight. We decided to ask about upgrades and got no help there. However, we tried again at the gate and hooray! We were able to change seats and had a comfortable flight to San Juan (and second breakfast).
We arrived in San Juan with no problems and immediately got a taxi to our first hotel, the Caribe Hilton. (Aside: because of the last minute planning, we used two free nights at different hotels and accepted that we’d be hopping hotels from night to night.) We checked in, dropped our bags, and had a late lunch at one of the hotel’s restaurants, Lola’s/Rustica – halibut with chorizo/pigeon bean stew; steak with risotto, and the house red wines.
We spent the afternoon outside, starting with a walk to Vieja San Juan, which took about 30 minutes from the hotel. After getting our bearings, we made our way to Don Ruiz for excellent pour-over coffee and pastries. After that, we continued to wander around the old city, trying to keep to ourselves. We happened upon Casa Melaza, a small rum bar and store that I had briefly seen a reference for, and we walked in for a tasting. We ended up trying seven or eight rums, buying a bottle of Don Q Seleccion Especial, selected specifically by Casa Melaza. Quite tipsy, we thanked our host and went back to the hotel (walking to the eastern edge of the old city and then taking Uber from there.







After freshening up, we went out for a late dinner at Santaella, which was amazing! We had morcilla curlers, goat cheese quesadilla, shrimp in garlic cream sauce with plantain trifongo, fried whole red snapper, and mud pie with a bottle of Guarachi Sunchase Chardonnay 2015. We got back to the hotel around 12:30am and crashed for the night.
Sunday
The hotel had only a breakfast buffet, which we were trying to avoid, so we started with coffee and pastry outside, enjoying the sunshine. We then packed, checked out, and walked over to have a fuller meal at Jose Enrique, a well-known farm-to-table restaurant. We met the most gregarious server we’ve possibly ever had, who attempted to persuade us the food was almost as good as his grandmother’s. We didn’t try his grandmother’s food, but what we had – morcilla, criollo, and egg; beef stew; mamposteao (browned rice with beans and ham), and cocktails – were just amazing.
However, during brunch we all got an emergency alert on our phones saying that the governor of Puerto Rico had instituted a curfew and was shutting down nonessential businesses. That was quickly followed by our restaurant reservation for that night being canceled. We thanked everyone at the restaurant and left to pick up our bags and switch hotels.
Hotel number two was the Intercontinental near the airport. We checked in and spent a couple of hours on the beach, soaking up as much as we could. Because restaurants were closed, we ordered room service for dinner – Greek salad, spaghetti carbonara, and a bottle of chardonnay. Not quite what we expected, but satisfying and filling.
Monday

We ordered a basic breakfast – a pastry basket with a pot of coffee – in the room, followed by some much-needed exercise to stand up and move around a bit. We decided to not linger longer and instead make our final hotel change of the trip, this time to the St. Regis on the northeast shore, about 30 minutes outside San Juan.
When we arrived, we were warmly but apologetically greeted by the general manager and staff, who upgraded us three levels to an oceanview suite (we presume at least partly due to their lack of guests). They also explained that due to the governor’s emergency declaration, the resort was basically shut down: we could use the beach at our own risk, but nothing else was open. We settled into our room and ordered lunch – mahi mahi sandwich, Cuban sandwich – before spending some time on our room’s balcony, enjoying the afternoon heat.
Dinner that evening was a green salad; snapper with chorizo and pigeon peas; orzo “risotto” with asparagus and mahi mahi, with a bottle of chardonnay as a welcome gift from the hotel (thanks to Virginia’s status).
Tuesday
We ordered a full breakfast to go with our complimentary pot of coffee and ate out on the balcony. After breakfast, we went out to the beach and sat for awhile. I took a brief walk until I ran into a staff member, who informed me that the governor’s proclamation included closing the beaches. I ran back to tell Virginia and we headed inside.
While having a light lunch in the room, we discussed whether it was worth staying if we can’t leave our (admittedly luxurious) room. We decided it wasn’t and changed our flights to the following day. We also let the hotel know, and they were gracious and understanding about it. Finally, we placed a grocery order to arrive two days later so we didn’t have to immediately go out when we got home. Having set our plans, we sat back with the last of the rum we had purchased and read through the afternoon.

We went more all-out for dinner – shrimp cocktail; kurobuta pork chops with coconut polenta and mushroom escabeche; Filet of beef with mashed potato and Gorgonzola; chocolate flourless cake with mango, coconut, and cilantro, with a bottle of Simi Alexander Valley Cabernet Sauvignon. Everything came out very well and we polished off everything.
Wednesday
We were up early to have breakfast and pack for home. We made sure to thank everyone we could see, checked out, and took a taxi back to the airport. Our flight home was full but thankfully uneventful. Having seen pictures of O’Hare’s Terminal 5 and the hours-long lines there, we were thankful we’d decided to stay domestic so we could leave more quickly. We picked up to-go food from Farmer’s Fridge and got a Lyft car home. Not the trip we wanted, but we enjoyed good food, soaked up some sun, and saw enough to want to return. Most importantly, we were safe, healthy, and home.

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