Friends, we just got back from an absolutely amazing trip to Puerto Rico a couple weeks ago. It was so good, in fact, that I couldn’t believe that we’d never thought to check out Puerto Rico — the very American island destination in the Caribbean — until now. Let me tell you about some of our favorite spots!
Getting There
Since we once again have our handy-dandy Southwest Companion Pass, aka my absolute favorite deal in the travel hacking game, booking flights from Dallas to San Juan, Puerto Rico (with a quick plane change in Florida) was a breeze. For around 27k Southwest points, which we earned through a combo of my work travel and spend on our Southwest credit card, the two of us had round-trip tickets for free.
Once we arrived, we found that Uber is a great way to get around the island, and the drivers are friendly and helpful. We took an Uber from the airport to our hotel for this trip, and between my conversational Spanish and our driver’s tourist English, she shared with us several great neighborhoods and restaurants we should check out on our visit.
Checking In
For this trip, we decided to stay at the Caribe Hilton in San Juan, Puerto Rico, and I couldn’t recommend it more highly. I’d been hearing great things about the Caribe since I started working at Hilton last year, and decided to use some of the Hilton points I’d earned using my new Hilton Aspire credit card to check it out.
We booked three nights, at a rate of 50,000 Hilton Honors points per night. And thanks to my Diamond status, we even got upgraded from a basic room to a wonderful Oceanview room with a balcony.
Even beyond just the room and view, though, this was a top notch hotel. In fact, since starting at Hilton I’ve had the pleasure of staying at 10 different Hilton properties (and across 6 of our 18 brands.) I can say without a doubt that so far, the Caribe Hilton was my favorite. From the private white sand beach to the swim-up bar to the fact that they invented the pina colada, I really loved our stay here.
Around the Island
Of course, we also didn’t spent a ton of time at just our hotel. On the day we arrived, we hit up the pool bar for a couple hours before changing for dinner and walking across the Dos Hermanos bridge, with beautiful views of the Laguna Del Condado, to reach our dinner spot.
Our first dinner was at Casita Miramar, and consisted of traditional Puerto Rican cuisine. I loved that the menu here consists of a whiteboard that they bring to your table, and is updated daily with the kitchen’s specials —no resting on laurels here! I got the Mofongo, a traditional dish of smashed plantains, seafood, and sauce. Meanwhile, the hubby chose a seared steak dish partnered with rice and beans. We both were utterly stuffed and couldn’t even finish all we ordered.
The next day, we set off to explore the Old Town portion of San Juan, starting with the Castillo de San Felipe del Morro. This fort (and many of the others in San Juan) is a National Monument, so if you happen to have a National Parks Annual Pass, you can get in for free!
The fort was very cool, and the hubby enjoyed geeking out on the old-time-y cannon placements and the like. But despite the fact that we were visiting at the end of January, and despite the fact that we had set out around 9:30 that morning, by the time we were done with the fort it was getting H-O-T.
We walked a few blocks to see some key old town sites (like the Plaza Colón and the Calle de Fortaleza), but by 11:30 or so we were in need of some air-conditioning! Luckily for us, we stumbled upon the adorable Café El Punto, which had one air-conditioned room in their primarily patio-service restaurant. And this actually ended up being one of our favorite meals in San Juan — the giant avocados alone made the stop worth it!
The afternoon was clearly asking to be enjoyed at the beach, so we didn’t fight the urge and headed to the private beach at the hotel. The water was warm and inviting, but did have a fairly strong current — I’m not sure that folks with small kiddos would have felt comfortable there. But for us, it was perfect.
That evening, we headed out of the touristy area of town to the up-and-coming Santurce district. Here we enjoyed happy-hour hopping at a few sidewalk cafes, taking full advantage of the people watching opportunities around La Placita, a locals hangout. I will say that we felt very comfortable and welcome here, but English was much rarer in this part of town — those without at least some basic Spanish skills might find this area a bit more nervewracking.
After happy hour, we headed to our main attraction for the evening, dinner at Vianda. This place is probably San Juan’s most hyped restaurant, having been written up in the New York Times, Eater, and others. The praise is warranted; we were quickly seated by one of the owners, warmly welcomed by our waitress, and stuffed with all our delicious selections for the evening. If I have one criticism, it’s that you’re not likely to find a lot of Puerto Rican cuisine in the dishes themselves, solely in their ingredients. Still, it was very, very good.
On day 3, we decided it was time to head further afield, and so we scheduled a Snorkeling Excursion and Beach Break to Icacos Island, via Catamaran. While we definitely enjoyed the snorkeling and on-board lunch sections of this trip, we felt like the beach break was a bit too long — after all, we had a perfectly good private beach back at our hotel! And also, with two seperate bachelorette parties on board, the fellow passengers got a bit too drunk as well…we would have preferred a quieter sailing. Still, it was nice to get to see more of the island.
Finally, on our last night in San Juan, we headed back to the Old Town to see some sites we’d missed the day before: strolling down the Paseo de la Princesa to see the many local vendors and the Raíces Fountain at sunset, watching the cruise ships set sail from the Bastión de las Palmas de San José.
Last but not least, we also managed to score a table at Verde Mesa, the restaurant credited with kicking off the farm-to-table movement in Puerto Rico. The key to getting in here is showing up when they open; while they don’t take reservations, they dole out wait times based on when you join the wait list…our 6:10p arrival meant a 7:00 dinner time. (However, those we noticed arriving at 7 were being quoted a return time 0f 8:45…)
Verde Mesa was my favorite meal of the trip, and that was among some very, very stiff competition. It was so good that I actually forgot to even photograph what the hubby was having, but I enjoyed a beef tenderloin served with kale salad and other roasted veggies. It was absolute perfection.
The following morning we had to get up early and bid adios to our newfound love of Puerto Rico. But if you’ve been thinking about booking a trip yourself, GO! As you all know, we travel a lot, and this was honestly one of the best return-on-investment trips we’ve made in a long time. I can’t wait to go back.
Been to Puerto Rico? Tell me what to do on my next trip in the comments!
