Travel Guide: San Juan, Puerto Rico
I was born and raised in Puerto Rico but my ambitions have taken me away to New England for the last 15 years. Darcy and I visit Puerto Rico as often as our schedule allows, usually two or three times a year. It’s lovely to spend a few days in the sunny weather with nothing to do but be with folks I love.
I get asked for recommendations all the time, by friends and friends-of-friends and guests at the restaurants. Our Google map-enabled list has all the places we like to eat & drink in San Juan, which is mostly what we do there, and we update it with every visit. There are a few on the list that I’ve been recommended but haven’t tried yet. Big thanks to my friends who tip me off to the new hot spots! Below, I am giving you my highlights with more ideas for your next vacation.
SEE THE FULL LIST
FOOD & DRINK
It should go without saying that my Google maps list has A LOT of good places to eat. I do my best to include notes with every place I have saved, so below are merely a few picks I want to expound on…
Have breakfast at La Ceiba: I have never seen a Spanish deli like this one and I find it has so many similarities to the Jewish delis of NYC. It is a very visible and modern legacy of the Spanish colonial period through food and pastries, and it’s just a vibe too… Imagine: Old men with Basque and Catalan family names who meet there daily. Lottery ticket sellers. Moms on a mission picking up coffee & pastries and bratty teenagers glued to their phones. It’s all there. Get the croquettes, the quesitos, the Spanish tortilla, a bocata ibérica, some coffee and whatever else looks good. Don’t sleep on the provisions and knick-knacks: I snagged all my authentic Valencian paella pans here for less than $5 a piece.
Dine in the patio at Cocina al Fondo: This was one of the longest-awaited restaurant re-openings post-pandemic and we loved our experience. The restaurant is housed in a small single-family house with a beautiful backyard. All happening on a side street off of bustling Avenida Ponce de León, a block behind a Marshalls store. Picture lush tropical landscaping, wrought iron patio sets and twinkling string lights, tall trees casting a cool shade, good music and drinks… All the food was tasty, well-seasoned and creative, and the dishes made excellently resourceful use of local ingredients. Chef Natalia Vallejo is a rising star with multiple James Beard nods. This is a one-of-a-kind experience! Plan ahead, only open Th-Sat and you’ll need reservations by text message.
Try fritters in Piñones: I loveeeeee Donde Olga and it has become a ritual for Darcy, Papi and me to waste a few hours here. Piñones can get ridiculously backed up on the weekends so I only visit on weekdays (but that said, the weekends are A VIBE). I drool at the sight of crab meat alcapurrias, the bacalaítos are fire, and I always get the octopus salad with a fistful of lime wedges and a thimble of hot sauce. Wash everything down with many, many icy Medallas. Marvel at the rustic open kitchen, where a seriously skilled fryer is shaping alcapurrias with a machete and a seagrape leaf. After your snack, hop back in your car and drive deeper into Piñones (just follow the road you took in) and see some beautiful beachy landscapes. Once you reach the bridge over the river, turn around and hit kiosks on the other side of the road on the way back to San Juan.
Eat fresh seafood for lunch at La Cueva del Mar: This place is reliably open, good for large groups and families, there’s valet parking and it has an extensive menu mostly focused on seafood but varied enough to please a vegan (my Papi). I love going for a late lunch and getting the fish tacos or the crab rice and making the most of mojito happy hour!
Dinner & pre-game at Pirilo’s Pizza: Pirilo’s is just a few minutes’ walk from our place so we end up there often. The pizza is very good, they are always open, the small plates are fire, prices are affordable and they have quaffable bottles of wine for $22-30. It is a great spot to start the night! Also great for families; not great for folks with limited mobility (the dining room is upstairs).
Fuel up at the local coffee shops: I am most partial to Gustos in Miramar for their outdoor seating, but there are many good options to try out. Check out Café Regina, Café Comunión, Café con Cé and Spiga.
NIGHTLIFE
Swanky night out at The Cannon Club in Old San Juan: This place is down the street from us and I am recommending it solely on the irresistible draw it has from street level. I have literally never been inside, even as I have walked past it so many times… I enjoy the buildup of intrigue with this one: The music spills into the street, there is sweet cold air conditioning, everyone looks so dapper. One day, I’ll wear something fabulous and step inside.
Sunset cocktails on a rooftop with a view at Bar Cathedral: Views of the San Juan Bay at sunset are pretty beautiful. The food here is by chef María Mercedes Grubb, who is very talented, well-regarded by the local community, and has great taste and flair.
Party on the street at La Placita: Everybody likes La Placita even though (or because?) it can be kind of a shitshow. It’s crowded and raucous. But drinking on the street is such a vibe! There is good food here as well; just look around at the restaurants in the perimeter of the square.
Cocktails and industry networking at La Penúltima: This bar on Avenida Ponce de León is one of the spots where local industry folks come to decompress, talk shit and have a stiff drink. I love this place, I love the patio where you can sneak out for a smoke without leaving the space, I love the insidery feel it has and I love being an anonymous fly on the wall when I’m there.
CULTURE
Visit the National Gallery of the Institute of Puerto Rican Culture (ICP): My incredible best friend from high school María del Mar curates this gallery and it is the best $2 you’re going to spend. There are seminal works of art from the 1800’s and there are modern pieces reflecting today’s struggle. This organization is part of the government but not very well funded, so the support of your visit really makes a difference.
Hang out in El Morro/El Totem: What a fun one for the families with kids! I have a lot of fun childhood memories visiting the El Morro fortress and buying a cheap plastic kite to fly it high with the crazy wind on the wide open lawn. This is a vibe on the weekends: there’s usually someone selling piraguas (snowcones) or ice cream and sometimes there is a fountain for the kids to splash around!
Visit the Museo de Arte Contemporáneo: This museum is located just steps from La Placita on Avenida Juan Ponce de León. There is a beautiful courtyard with a glass ceiling inside and the art is provocative and very current. Afterwards, walk a few blocks to La Placita and enjoy a beer and some snacks around the square. I suggest Asere for mojitos and Cuban food.
Pick out a traditional guayabera for the boys: Guayaberas are linen shirts for men with intricate pintucks, buttons and other motifs, and they are considered Caribbean formalwear. I personally believe a crisply starched guayabera can make every guy look super handsome. This is a unique souvenir to bring home.
See the murals in Santurce: Around the Parada 15 area there are a lot of incredible large scale murals. The best idea is to pick a destination bar and go on foot, you will see plenty of incredible art in this humble neighborhood. El Watusi is a good spot to orient (or disorient?) yourself.
Buy local art: Old San Juan has some galleries and it doesn’t take much exploring to find them. I really like Memories of Old San Juan and have purchased art there for Little Sister. Galleries can help you package your piece for travel or coordinate shipping back home.
CHILL
Walk/run around at sunset: There are a few good walks to enjoy the dying sunlight and you will see people exercising as well as strollers. Try going around the lagoon in Miramar to Condado over the bridges or the boardwalk by the ocean at Puerta de Tierra, going from Old San Juan to the Escambrón beach, both about an hour’s walk at a leisurely pace.
Stroll down Paseo de la Princesa: Come around early morning (8 am) or sunset, otherwise it can be too sunny and warm to go on a walk outside. Paseo de la Princesa is a boardwalk/promenade in Old San Juan that —along with Paseo del Morro— covers the length from La Puntilla (southernmost tip) to El Morro. You can end your walk at Puerta de San Juan, close to the governor’s mansion. This is history and also such a vibe for any kind of photoshoot, even for the ‘gram.
Watch a foreign film at Fine Arts: I like the Fine Arts Miramar theater for Puerto Rican and International movies and make time to go with each visit. They serve wine and beer and have super plush seats. Some indie/artsy American movies are also shown with Spanish subtitles. Catch a matinée in the afternoon or plan to go before dinner.
Go to the beach: I’m not super beachy and San Juan is not known for its beaches, so I pick my beach to be conveniently close to food. El Escambrón is great and across the street from El Hamburger. Ocean Park beach is adjacent to Condado/Santurce/Isla Verde and two blocks away from La Cueva del Mar in Calle Loíza.
PLACES TO STAY
For a multitude of reasons, I strongly suggest staying in a licensed hotel in an area that caters to tourists. I strongly discourage you from staying in residential neighborhoods.
Old San Juan: Old San Juan is our homebase and there is nowhere prettier to wake up in the city. In the mornings, we descend onto the street to be greeted by the hustle of morning dropoff at the Abraham Lincoln elementary public school. I’m always smitten by the common courtesy Puerto Ricans share to say “good morning” as we walk alongside neighbors and City Hall workers and converge for coffee at Plaza de Armas. I would suggest checking out Hotel El Convento, Hotel Palacio Provincial and The Gallery Inn. Beware: Old San Juan is really isolated from other parts of town. You will need access to a car or Uber and a lot of patience if you are trying to enter/exit during the weekend.
Puerta de Tierra: There is not a ton to do in Puerta de Tierra but there is the Caribe Hilton, my favorite hotel in San Juan. The Caribe Hilton has the best, most expansive views; it has a good beach AND a good pool (IYKYK) ; it has super cool retro vibes and a lobby bar with live music; it is private and secluded but easily accessible by car.
Condado: This area has major Miami vibes and most hotels are here. Beach, drinks, loud noise, car traffic at all times. Candidly, I like it but I don’t love it. But I do love the Condado Vanderbilt! If you have a zillion credit card points burning a hole in your pocket, drop them on a suite at the Condado Vanderbilt. From Condado, you can easily walk to Santurce and Miramar and do more things.
Isla Verde: If you came to Puerto Rico just to go to hang at the beach, you could stay in Isla Verde. It is technically not in San Juan, but the next city over called Carolina. There is a string of large hotels on Avenida Isla Verde and my favorite is El San Juan Hotel y Casino. They have beautiful pools, a stunning hotel lobby bar with so much fun live music, and a pretty bumping club called Brava where you can get blasted and conveniently stumble back to bed…
GETTING AROUND
There is a public bus system called the AMA but in practice you will struggle to get around by public transit. San Juan is very car-centric and you will do better hailing an Uber or Lyft ride. The prices are generally affordable and locals are generally friendly if you are too.