Where to Stay, Eat and Drink in San Juan, Puerto Rico

From hotels to fine dining to gastropubs to every kind of bar, we can help make your trip perfect.

Just checking in…81 degrees and sunny skies! #VanderbiltLife #winterweather #wanderlust

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At the start of February, I was having a palm tree tattooed onto my forearm in Old San Juan, Puerto Rico. I’d escaped New York in winter to research a story; the gift of ocean views and bare arms a blessing I didn’t want to forget, and so I stole some time to visit Senzala Tattoo. I never totally escape my work, though: The guy at the front desk and I chatted about vegetarian options on the island and in New York. As the work was being done, he came over to me to gush about the food on Bed-Stuy vegan restaurant Toad Style’s Instagram, which I said he’d have to visit on his next trip up. I knew I had made the right rash decision by stopping in.

In less than two years, I’ve traveled down to San Juan, Puerto Rico—which languishes between independence from the United States and statehood—five times, for work and vacation both, growing attached to what I’ve come to consider my second home. My recommendations, then, are rooted both in knowledge and highly personal experiences: I’ve interviewed most of these chefs and done shots with many of the bartenders. But I hope I can inspire you to hop on a plane. As New Yorkers, we’re lucky to have access to many daily flights down to this island that has such addictive flavors and intense energy. You might just find yourself going back as much as I have (commemorative tattoos optional).

To stay

For luxury: Condado Vanderbilt Hotel
If you want to step into a hotel and be offered a glass of Champagne, stay at the Condado Vanderbilt. There’s an infinity pool that looks out onto the ocean, an adults-only pool and hot tub, and—best of all—excellent food, from the pool-side bistro Ola, where you can order a perfect avocado toast for breakfast, to the fine-dining 1919 (more about that later). The rooms are plush, and the bathrooms come stocked with C.O. Bigelow toiletries.

For history: El Convento Hotel

This building in Old San Juan was originally (you might have guessed it) built as a convent. Construction on the Spanish colonial space, which sits next to the second oldest cathedral in the western hemisphere, began way back in 1646, but the most current renovation happened in the 1990s. There’s a rooftop pool, a roaming cat named Trixie, and delicious food by chef Luis Castillo, who’s created a rooftop garden at the hotel where he grows herbs he incorporates into his exquisite dishes.

For meditation: The Dreamcatcher

Let's have breakfast ?outdoors #nowinter #summerallyear

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In the very quiet, secluded Ocean Park neighborhood, you’ll find The Dreamcatcher. The rooms have no TVs, there are outdoor showers, and the kitchen is completely vegetarian. Here you’re walking distance from the beach and the excellent Ashtanga Yoga Puerto Rico studio.

To eat

For fine dining: 1919 Restaurant

Some evenings, we start with dessert…. #foodie #1919Menu #TheVanderbiltLife #FineDining

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Chef Juan Jose Cuevas (a Blue Hill alum) creates magic in this restaurant’s gorgeous setting; if you’re seated well, it provides ocean views during your meal, so make a reservation for sunset. During a specially prepared seven-course vegan meal, he shocked me with a mastery of plant-based cooking that is rarely achieved—especially not by an omnivorous chef. From the amuse-bouche of an avocado gazpacho to an intensely herbaceous chilled eggplant salad (pictured up top) to a grilled bok choy that ranks among the best dishes I’ve ever eaten, the meal was incomparable. To finish the experience, pastry chef Nasha Fondeur served a mango sorbet that was just on the right side of too-sweet, complemented by local citrus.

For knives and lipstick: Gallo Negro

TTT : Tuna Tartare Tostada #valentinesmenu #uni #tuna #mexicancuisine #tacotuesday

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Chef Maria Mercedes Grubb cooks what she wants to eat, and it shows. The always fun menu can run the gamut from bibimbap to tacos to Indian-spiced fried cauliflower (cutely named Punjabi Coliflow). Grubb, who trained in New York City, has the chops to pull it all off. Don’t miss the happy hour $.99 cent menu, either, where she cooks bites like a pâte crostini, curry deviled egg and chicken wings in various flavors. Her vegan dishes, too, are must-orders. Sit at the bar, order a cocktail and hang.

For a taste of the new school: Lote 23

cold brew tonic from @caferegina_pr ?#lapiratainpr

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This brand-new food lot in Santurce has taken the typical Puerto Rican food kiosk and kicked it up a notch by bringing in both established and new chefs to hawk their bites. Don’t skip El Baoricua, from chef Paxx Caraballo Moll—they stuff Taiwanese bao buns with Puerto Rican flavors in a mash-up of cross-cultural island flavor. Order the vegan kimchi, which moves from spicy to sweet to smoky, and anything with the house-made banana ketchup. Definitely get a Café Stormy from Café Regina, which blends cold brew, cardamon, coconut, ginger beer, cacao and lime in one beautifully refreshing cup. If you’re a meat-eater, hit Pernileria Los Próceres from chef Mario Juan, who’s always cooking up something audacious. In truth, though, you can’t go wrong here.

For a gastropub: Parcela

If you’re staying at the Condado Vanderbilt and want a more laid-back atmosphere, head over to Parcela, where the always-changing menu by chef Sebastián Ramírez pairs perfectly with both beer and the great house cocktails. One recent dish was a salad of beets, pickled romanesco, goat cheese, watercress, walnut and sorrel in a bourbon vinaigrette.

For a true taste of Puerto Rico: La Jaquita Baya

Chef Xavier Pacheco sells produce grown on the island right inside his restaurant, a temple to Puerto Rican cuisine. If you don’t order the pigeon pea escabeche, please think hard on your choices—the exquisitely acidic dip served with salty tostones is a dish I dream about.

For the island’s most famous chef: José Enrique

came back before the airport for breadfruit mofongo / thx, @paxxito ! / #vegan #lapiratainpr

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He was long-listed for a James Beard Award this year and in 2013 was the first Puerto Rican chef to be named one of Food & Wine’s Best New Chefs. Don’t expect anything snooty, though: This place is casual and nondescript, while the food is anything but. A breadfruit mofongo I had on one visit had me melting into my seat. (It should be said that you should order any and all breadfruit dishes when in Puerto Rico.)

For surprisingly great Thai: Mai Pen Rai

It's going to be a great weekend! #Pho Special with all the fixin's. Limited quantity, so don't miss out!

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When you want something very spicy but a bit on the lighter side, head over to Mai Pen Rai. All your favorite dishes are here, along with a bánh mì and pho selection.

For the pescatarians: Verde Mesa

Date night in Old San Juan should be spent here, in what might be the most adorable restaurant in the city. The food, which focuses on vegetables and fish, never disappoints.

To drink

For a party: La Factoría

It’s considered one of the 50 best bars in the world for very good reason. Get there early to grab a seat and order my personal favorite, the Peligroso, which boasts Ron del Barrilito rum, Averna, Campari, Angostura bitters, dry spices and citrus. If you’re there while Carlos Irizzary is working, consider yourself lucky. You can spill a daiquiri on him and he won’t miss a beat, and if a creepy guy offers to buy you a drink, he’ll refuse for you (I may or may not have personal experience in both these scenarios).

For a classic dive: El Batey

The walls here are covered in the writing of years and years’ worth of guests. Order a Medalla (a local beer, perfect for the heat) or rum and coke, then look through the very random jukebox selection.

For molecular mixology (or a backyard beer): La Penúltima

This newcomer, on the outer edge of La Placita de Santurce area, is where you should order vegetable dumplings and a carbonated Negroni. The bartenders are knowledgeable about the latest centrifuge on the market yet the vibe is chill; you might feel like you’re back at your favorite bar in Brooklyn.

For a taste of the tropics: Jungle Bird

you ferment pineapple, i show up ? #lapiratainpr

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From the folks behind La Factoría comes Jungle Bird, named for the tiki drink but offering far more than tacky glassware and over-the-top sweetness. On a recent visit, they were serving a piña colada made with tepache—fermented pineapple—that I could live on if only it provided enough nutrients.

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Alicia is the associate editor of Edible Manhattan and Edible Brooklyn.