It is getting cold back in New England (15-30˚ F this last week), so we were determined to head south. Last year was the first of what we’d like to establish as an annual tradition, a tropical family vacation. We went to Aruba last year (yes I will go back and write it up!) and have been eager too return to Puerto Rico (PR). PR is under-appreciated in the mainland US, and we’re almost hesitant to expound on the many reasons why.. but here’s a start!
- Huge variety of beautiful landscapes (mountains, limestone karst, rainforest, beaches)
- Relatively short flight (4 hours from Boston)
- Relatively inexpensive to get to (San Juan, along with Antigua, are the primary hubs for Caribbean flights)
- Easy (US so many things like phones and currency are the same)
- Relatively inexpensive to be there (little lower prices than US averages)
- Filled with wonderful restaurants (and you don’t have to go fancy to get amazing flavors!)
- Has some of the best beaches in the world (yeah I mentioned that already but for many this defines a tropical vacation!)
- The European vibe in Old San Juan is strong!
- Only one hour ahead of the East Coast
- Last but surely not least- the people are colorful, friendly, welcoming, and all-around great.
We have been to mainland PR and the islands of Vieques and Culebra several times, so we are able to be a bit more selective on this trip. We also only have 5 days so.. we’re staying in Old San Juan. This is also Leanna’s first trip to PR, so we want to make sure she sees some highlights!
We got to Logan around 4:30am so it was a long day. We parked in the economy lot, which is a significant distance through the cold from the terminals. The shuttle was ready for us though so no complaints.


The flight was freezing cold, so the jetway off the plane was an immediate relief. No checked bags and SJU is small so we were out into the humid, warm weather very quickly.

We’re staying right in the heart of Old San Juan, off of Calle Cristo. The streets are the classic bluish brick, which has the European look and feel of cobblestone. I could easily spend a day just taking pictures of the street.

We were starving when we arrived so we walked to El Jibarito, an old favorite for local cuisine. It has changed.. and sadly not for the better. It is super busy (we waited in line for over 30 min at 3:15pm on a Sunday), which I guess is good news in a way. The menu is still simple, but the prices have skyrocketed well beyond inflation. Most importantly, the food was hit-or-miss. None of it “bad”, but the pork that they specifically said was moist and flakey was dry. It was tasty though, and once we added some garlic cream sauce of some sort it partially redeemed itself. The garlic shrimp was delicious and perfectly cooked, although they managed to include a couple clumps of salt that caught Ashok off-guard. The mofongo was quite good, although I’d say would also benefit from some sauces! The chicken was spot-on, as was the sweet plaintain..

On the way to dessert.. we had chocolate at Montadero Chocolate, a 100% Puerto Rican chocolate shop. The power was flickering for some reason so it was hard to see the details but the flavors were strong and we had a nice chat with the proprietor.

We went to Anita’s Gelato for our REAL dessert. It was packed, with a line snaking the length of the room thrice.


We tried a ton of flavors and settled on chocolate cookie (that’s accurate but doesn’t capture the unique essence of the dark chocolate base with chocolate bits), some sort of caramel swirl, strawberry, sugar-free hazelnut (surprisingly good!), black forest, and a vanilla-based cookie. The prices were really high here too, which may end up being a theme of this trip.



When we left Anita’s, we saw that Calle de la Fortuleza was fully illuminated and a show of some sort was coming.


It ended up being a light show projected onto La Fortuleza (the Governor’s Mansion) itself. It was.. interesting and only about 5 minutes long,


Great backdrop for some group photos!


Back to the AirBnB where I think we all fell asleep within 5 minutes.. then got back up later to finish off the evening.

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