How To Eat & Drink Your Way Through A Delightful Week In Puerto Rico

A few months back, my husband and I were searching for a vacation spot with a few non-negotiables: We wanted to travel to a destination neither of us had been to before and didn’t want to fly more than a few hours from home. My definition of relaxation is being by the water; he likes to hike and snorkel. We both love trying new restaurants, wandering around cities, and exploring museums and historical landmarks.

For a minute, finding a place that ticked all those boxes felt like a Herculean effort, but then I realized neither of us had never been to Puerto Rico, with its beautiful beaches and rainforests — and, of course, the capital city San Juan. Plus, it’s an easy flight from New York. We were sold.

We got an offer to stay at the Condado Ocean Club, a boutique hotel on the Atlantic Ocean about 15 minutes from the San Juan airport. The decor is bright and airy — whitewashed with pops of blues — and although the waterfront area is small, and the surf is rough, the shoreline is a beautiful spot for a morning stroll. (Regardless, you’ll probably want to spend most of your time chilling in one of the lounge chairs lining the infinity pool, margarita in hand.) We stayed in an oceanfront room with floor-to-ceiling windows which, when we opened the curtains every morning, revealed dramatic views of the blue-green Atlantic.

As much as we could have enjoyed hanging poolside our entire stay, we did a lot of exploring, from hiking El Yunque National Forest and walking all over Old San Juan to taking day trips to nearby beach towns. Oh, and we ate. Ahead, all the culinary highlights from our five-day trip in and around San Juan.

Make Friends Waiting In Line At Bebo’s Cafe

We arrived in San Juan just before dinnertime, so we grabbed a glass of rosé at the hotel bar, Social. The space is modern and sleek, with cool grays and ocean tones, and we promptly hit up the friendly bartenders for restaurant recommendations. (Past me used to plan vacations and meals within an inch of my life; nowadays, I’m still intensely Type A but I also enjoy seeing where the day will take me — and I’ve learned that local recs are often the most spot-on.)

They conferred before writing down a slew of suggestions on a napkin for us. We wanted traditional Puerto Rican fare for our first meal, so we landed on Bebo’s, a no-frills spot where we chatted up locals and fellow tourists as we all waited for a table. We shared empanadas before moving onto a tender ropa vieja with rice and beans and sliced avocado (for me) and chicken in garlic sauce (for him).

Eat Tacos & Stroll To The Shore

For lunch the next day, we checked out another local rec, Acapulco Taqueria Mexicana, a cozy two-level taqueria. We grabbed a high top on the main level, where we started with guacamole and micheladas and then ordered, you guessed it, tacos: carnitas, made from Michoacán-style confit pork and served with onion and cilantro, and chicken, which was marinated in achiote, orange, and chipotle.

Afterward, we strolled over to Pirilo Pizza Rústica, where we had a glass of rosé and made friends with a couple sitting next to us who, coincidentally, happen to live in our neighborhood in New York. We capped off the afternoon with a short walk to Ocean Park Beach a few blocks away.

Enjoy A Cozy Supper At One Of San Juan’s Buzziest Spots

As we headed up the steps and into Casita Miramar, located in the upscale, mostly residential Miramar neighborhood, it felt as though we were walking into someone’s house. It’s a maze of rooms, but once we were led to our table we enjoyed complimentary crackers and pumpkin/root vegetable soup before moving onto an appetizer of white bean hummus, which we spread onto crusty sourdough. The restaurant’s known for its goat stew, which is braised for three hours in red wine and sofrito, as well as carne frita — a confit and smoked pork duo with garlic, red onions, and plantain crunch. Just don’t forget to make a reservation, or else be prepared to wait an hour or more.

Dine Al Fresco & Enjoy The Ocean Views

Mid-trip, we were tired from a long day of hiking in El Yunque National Forest and a late lunch at La Parilla, a restaurant overlooking the beach in Luquillo, so for dinner we kept things easy by popping down to Social again. The menu features Puerto Rican cuisine with a modern, global twist. I had a Mediterranean salad with grilled chicken (the dishes change seasonally — a peach and prosciutto option is on offer right now) but I can’t say I wasn’t tempted try their spicy tuna tacos or the ribeye, which is served alongside chimichurri and truffle mac and cheese.

Pro tip: Grab a seat outside overlooking the ocean like we did, where you can take in the salty air and listen to the crashing waves as the sun goes down.

Have Lunch At A San Juan Classic

The first thing to know about La Casita Blanca, one of San Juan’s most popular and well-known restaurants, is that you should expect a bit of a wait: Even at lunchtime on a weekday, like when we went, you can expect to find folks lined up outside for a table. Once you’re inside, however, you’ll find the same homey vibe as its sister restaurant, Casita Miramar. The decor here is airier, with white shiplap walls and plenty of plants nestled among copies of the restaurant’s cookbook, and we once again felt like we’d just stepped into a friend’s house.

As waiters brought around chalkboard menus, we were offered complimentary soup and shrimp crackers, similar to our experience at Casita Miramar. We tried the chicken stew and the beef stew, as well as alcapurrias, Puerto Rico’s answer to fritters, which are made from masa dough and filled with savory meat. Don’t leave without trying the restaurant’s goblet-size portions of sangria.