An Old San Juan stalwart since its opening in 2013, La Factoria has expanded in the years since into an institution, often appearing on the list of the World’s 50 Best Bars. It is still a go-to for its Lavender Mule, where lavender gives floral balance to a Moscow mule; the La Champeta, with Don Q Añejo rum, pineapple, and fermented ginger; and the Garibaldi Criollo, where Campari is infused with acerola, a Caribbean cherry. If wine is desired, Vino, right behind the main bar, provides a selection.

Beer bar Lúpulo is always blasting the best playlist and serving a wide array of beers on draft as well as in bottles and cans. Focus your drinking efforts on local breweries, such as those from Boxlab in Aguadilla on the island’s west coast or Zurc Brauhouse in Coamo. Everything pairs well with the bar food selection, including some truly wonderful French fries and an excellent Cubano.

Old San Juan’s Plaza de Armas bustles during the day as locals, visitors, and  office workers descend on the area’s coffee kiosks. At night, though, it tends to quiet down. Here, far from the dives of Cristo and San Sebastían streets, wine bar Pío Pío serves a big menu of sparkling wine, paired with seasonal small plates like oysters Rockefeller; beef tartare; and a salad of chrysanthemum greens, silken tofu dressing, hazelnuts, and chayote. There’s even a Negroni  piragua, a decidedly adult take on the local street cart treat of shaved ice and  flavored syrup. 

Tiny but mighty, Spiga is a beloved Old San Juan gem that bakes its own sourdough loaves daily for sandwiches and toast, as well as chocolate chip walnut cookies no one leaves without. Breakfasts of scrambled eggs with tomato, spinach, and feta are simple, but made special by the bread; for lunch, there are daily house-made pastas, occasional lasagna, and satisfying salads.

This French bistro in Old San Juan is known for its weekend brunch, with mushroom and blue cheese quiche, but the dinner, too, lives up to the hype. Here, the classics are on offer, from duck confit to coq au vin to trout amandine, in a convivial atmosphere that will take you out of the touristic restaurant path just one block away.

Seafood bar meets wine bar at Celeste in Puerta de Tierra, an area nestled between Old San Juan and Condado. Chef and proprietor Sebastián Martínez Tully prepares elegant dishes inspired by Puerto Rico’s bounty. The squid ink ceviche, aged tuna with Meyer lemon, tamarind brown butter anchovy toast, and grilled sepia are not to be missed. The carefully curated wines come from small wineries. 

This upscale cocktail bar on Calle Cerra hosts an eclectic mix of artists, industry professionals, and anyone looking for a superb cocktail. In an area known for outdoor hangouts with cheap drinks, Machete serves up classic cocktails and creative house drinks made with beets and carrots. The bar food here is top notch, including a perfectly cooked burger, cochinita pibil tacos, and fried cauliflower. Arrive early for a seat or expect to stand for the entirety of the night. There’s an outdoor patio in the back worth checking out.

Chef and owner Carlos Portela’s menu changes almost daily and is driven by the produce, fish, and meat available from his local purveyors. The prix fixe menu could be anywhere from 15 to 24 courses, and the experience can last up to five delectable hours. The wine pairings, chosen and poured by chef Portela himself, are equally impressive. Dining at Orujo is like going to a jazz concert and a symphony rolled into one, with bursts of improvisation and moments of exact precision.

Chef Ruben Guzman’s superb cooking over an open fire makes the Miramar Food Truck Park a must visit destination in San Juan. Signature dishes include the choripán sandwich with chimichurri, roasted chicken thigh, and grilled catch of the day, often spearfished by chef Guzman himself. The grilled eggplant is a superb vegetarian option.

After shutting down her Miramar restaurant when the pandemic hit, chef Natalia Vallejo returned with a bigger space at Cocina al Fondo, where she quickly earned a James Beard semifinalist nomination. A charming renovated  house with an ample backyard provides a stunning setting for her updated, vegetable- and seafood-forward takes on Puerto Rican cuisine, skipping over well-known staples like mofongo to focus on deeper cuts. Vallejo serves a terrine of beet and goat cheese with toasted bread, pastelillos (or empanadas) filled  with pumpkin, ají dulce (a local sweet pepper) fried tempura-style, buñuelos of mashed root vegetables, perfectly cooked catch of a day, a vegetarian pastelón, and much more on the newly expanded menu. Dessert, a cocktail list by Karla Z. Torres, and a thoughtful wine selection aren’t afterthoughts, but complementary to Vallejo’s cooking. 

When the occasion calls for a fancy dinner, there is none better than 1919, where chef Juan José Cuevas uses local produce, meat, and seafood to create exquisite tasting menus that can be made vegetarian or vegan upon request. Located inside the luxe Condado Vanderbilt Hotel, the food has far more substance than the big hotel-style environs might suggest, as Cuevas cooked at New York’s legendary Blue Hill before returning home to Puerto Rico to give local ingredients the fine dining treatment.

Long before the doors open, there is a line outside full of patrons waiting to grab a prized seat at San Juan’s newest pizza spot. Helmed by chef Francis Guzmán of Vianda and his longtime friend from culinary school, chef Stephen Reyna, La Santurcina is exactly the pizza place San Juan needed. The Neapolitan-inspired sourdough pizzas are topped with quality ingredients, and many are vegetable-forward, like the Beetaroni and Zucchini Ricotta. The fried olives and lemon-caper wings are great starters.

Simply put, Mexican food in San Juan has never been great. But Los Guapos, from chefs Xavier Pacheco and Gaby Antúnez, is turning the tide with fresh ingredients and care. The burritos, chilaquiles, and micheladas are especially superb, making it a go-to for weekend lunch. 

This industry hangout came back from the pandemic with a natural wine selection and revamped (but still exceptional) cocktail lineup. The new drink menu features a martini infused with sesame, a daiquiri made with the local agricola rum Ron Pepón, and a spicy hibiscus margarita. Thankfully, the food menu is just as well executed, with bar food you’d expect like wings and burgers, plus veggie lo mein, smoked gouda croquettes, and a barbecue portobello sandwich.

Chef Kelly Pirro has created a menu with a focus on Southeast Asia, which is a refreshing alternative to the abundant Chinese and Japanese restaurants. Thai curries, banh mi, a healing tom yum soup, and satisfying laab. This is also one of the most vegetarian, vegan, and gluten-free-friendly restaurants in San Juan, making it a safe bet when one has a varied party to entertain.

Tucked behind Cocina Abierta (worth a visit on its own), Oriundo is chef Martín Louzao’s newest experimental concept. Louzao, a long-time restaurateur and creative, pays homage to Puerto Rico’s forgotten and underutilized ingredients in a monthly dinner series. Seatings are announced on the restaurant’s Instagram page and sold out within hours. Each dinner includes prix fixe menus for omnivores, pescatarians, and vegetarians, along with thoughtfully selected wine pairings by sommelier Michelle Negrón. A few recent pop-ups paid tribute to pana (breadfruit) and the Caribbean land crab. Top chefs from the Caribbean and Latin America frequently make appearances, showing up with native ingredients of their own. If you can score a reservation, you’re in for a memorable experience. 

After staging with chefs Gastón Ocurio and Rafael Osterling in Peru, chef Rafa Ubior returned to his native Puerto Rico to open Sur, a Nikkei spot in the heart of Santurce. Here, chef Ubior fuses classic Japanese and Peruvian cuisines with locally sourced ingredients and a strong focus on sustainably sourced fish. The raw bar doubles as a cocktail bar where you can sip on a superb Negroni or grape pisco sour, paired alongside a red snapper tiradito, ají amarillo ceviche, or octopus tempura sushi roll. High Kitchen, the sister restaurant and food pantry next door, serves the best fried chicken in town (weekdays, lunch only).

After an inspiring month-long trip to Israel, chef Rául Correa opened Tía Dora alongside longtime friend and sous chef, Juan Lebrón. The duo plate up Mediterranean-inspired dishes that are a pleasant addition to San Juan’s dining scene. Dishes are meant to be shared. Start with any of the spectacular mezze, including labneh with confit tomatoes, followed by lamb kebab, pasta with local mushrooms and coconut ragu, and salmon with chermoula. Located in Ocean Park, Tía Dora is a great post-beach option.

Minutes from the San Juan airport, Piñones is a rustic neighborhood deeply rooted in African tradition. It’s famous for its beachside shacks hawking endless frituras, or fried foods, including the favorite, Kiosko el Boricua. Locals line up for the handmade alcapurrias, a green banana and yautia fritter filled with meat or crab, pastelillos filled with the same, and fried rice with jueyes, or crab. Wash them down with a cold Medalla, the local light pale lager that cuts the fat of the frituras and cools you down in the sun.