This charming spot in Old San Juan is a cafe by day and bar by night. Spearheaded by chef Martin Louzao, the menu changes constantly, driven by what’s in season. While the food is memorable on its own, every detail has been thought out, from the beautiful amber glassware to the unique tiles made from coffee beans. Located on a charming, tree-lined street adjacent to the Catedral de San Juan Bautista and Hotel el Convento, Caleta Cafe’s dreamy location is the perfect backdrop for sipping on a glass of wine as the evening comes on.

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-infused take on 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 Brauhaus in Coamo. Everything pairs well with the selection of bar food, including some truly wonderful french fries, wings, and an excellent Cubano.

After a long hiatus, chef Gabriel (Gaby) Hernández finally reopened Verde Mesa in 2023. The restaurant returns to its core mission as a seasonal, vegetable-forward establishment, but the kitchen team has reemerged with renewed creative force. Hernández can be found at farmers markets every week, sourcing ingredients like pomarossa, jobo, star fruit, and breadfruit. The menu, which takes cues from the Mediterranean, features small dishes that are most fun when shared. Save room for the purple cloud: a fruity, creamy, meringue-based dessert.

In Old San Juan, Deaverdura is a staple of comida criolla, the Puerto Rican cuisine that blends local Taíno ingredients with Spanish and African influences. Pasteles, carne frita, tostones, and more create glorious smells wafting from the kitchen into the street, which explains why this corner stop is always drawing a crowd of locals and visitors alike. While the menu is meat-focused, there is seafood and they’re always able to do vegan and vegetarian dishes as well.

Natural wine bar El Vino Crudo operates in an expansive space in Old San Juan that maintains all the character of the old city while coming off beautifully minimalist and modern. It operates as both a shop and bar, so take the opportunity to pick up some bottles for the beach, especially since the importers are attuned to the hot weather, providing lots of light reds, rosés, and skin-contact wines. El Vino Crudo is a chill experience in a city where drinking spots tend to get rowdy, making it a respite to enjoy a glass with olives, local cheeses, and other seasonal Italian dishes, such as an herby citrus salad or bucatini carbonara. Check the bar’s Instagram for pop-ups by guest chefs.

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 menu changes quarterly but it always starts with a selection of crudos such as squid ink ceviche or aged tuna with Meyer lemon, followed by items like tamarind brown butter anchovy toast or grilled sepia. 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 octopus, fried cauliflower, and cochinita pibil and mushroom tacos. 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.

They don’t take reservations at this narrow Miramar ramen joint, so arrive early — though if you have to wait, it’s well worth it for their house-made noodles, intensely spicy vegan broth, various mazemen preparations, and katsu. The appetizers, such as fried trumpet mushrooms, potato croquettes, and edamame, are filling, so order accordingly. This is an excellent spot for those who don’t eat meat, as there are three vegan ramens to choose from.

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 Award. 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.

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.

Diego San Miguel opened this bakery in Cupey, a San Juan suburb, and in a few months made it a destination where items sell out daily. Options include sourdough breads, a selection of wines, cheese, and other high-end pantry options, as well as some pastries and local sweet breads, such as Mallorcas. Thursday night pizza is a real draw, when the line extends into the parking lot for New York-style pies, often made by local guest chefs.

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 red snapper tiradito, ají amarillo ceviche, or octopus tempura rolls.

Regina evolved from a spot at an outdoor food hall to a tiny outpost on Calle Taft and finally to a full-scale cafe and restaurant. Among the city’s traditional panaderias serving Cubanos and media noches, Café Regina fills a void for light, creative takes on breakfast and lunch dishes, signaling this approach with an airy, bright space. On the rotating menu, check out the avocado toast, which may come adorned with black garlic and pickled radishes, or sandwiches on quality breads stuffed with fun ingredients like artichoke mayo and onion jam. Pair your meal with a cold brew or frothy cappuccino.

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.