By Travel & Leisure
October 09, 2014

Situated on a narrow island north of Condado and Isla Verde, Old San Juan offers a timeless escape steeped in centuries-old history and infused with modern appeal.

A city within a city, Old San Juan is connected to mainland Puerto Rico through a series of three bridges, the Puente Dos Hermanos, the Puente G. Esteves, and the Puente San Antonio. Away from the busy Condado beachfront and the gaudy casinos of Isla Verde, it’s a peaceful haven of charming colonial architecture, fascinating history, and unforgettable dining, which you might miss sipping pina coladas poolside. Deemed a National Historic Landmark District last year, more than 40 years after being listed on the U.S. National Register of Historic Places, Puerto Rico’s oldest settlement offers a delightful collision of old and new best explored on foot.

Explore Surprising Contrasts
Within its hilly streets, the link between past and present reverberates in small restaurants with a cosmopolitan edge, old-school bars, and antique-clad hotels. Under the bright sun, the tiny cobblestone streets provide a looking-glass-like step back in time with facades painted pastel blues, pinks, and yellows and wooden balconies packed with bright flowers and chipped terracotta pots. Nearby opulent palaces channel an era of once powerful families, like the Ponce de Leons, however, amid the fading grandeur there are constant pops of fresh energy as you discover boutiques and cafes. Somehow these modern shops and tiny eateries feel right at home behind the wrought-iron details and colonial spaces they inhabit. While they might be housed in centuries-old buildings, they have cutting-edge jewelry, inventive menus, and trendy statement pieces that are absolutely of the moment. Heading out to the city’s dramatic edges, the cerulean sky provides an especially stunning backdrop to the iconic forts, the Castillo San Felipe del Morro and the Fuerte San Cristobál, connected by the scenic Calle Norzagaray path. Further along the coast, on the North Wall, a small boutique hotel filled with vintage bric-a-brac offers conquistador-worthy views of San Juan Bay and the mountainous mainland in the distance.

Take in the Local Color
Returning back to the interior and taking a break from the scenic outlooks, the city’s plazas provide a lively sampling of local life. During the day, soak up the sun and people-watch with a piragua traditional shaved ice drizzled with flavored syrup from a street cart, or spend Saturday wandering through stalls at a pop-up, organic farmers market selling fresh produce, like locally grown sweet mangos, speckled dark-green calabaza pumpkins, and plantains, depending on the season, as well as flowers, handicrafts, and more in the courtyard of the Museo de San Juan. Grab a plastic chair and snack on vegetarian food from one of the small stalls, serving up Caribbean-influenced fare like burritos with papaya hot sauce, or cool off with fresh-pressed juices, like cantaloupe and ginger. In the evenings, local street musicians turn the plazas into al fresco stages playing a mix of Latin music, from salsa and merengue to bachata; which has been known to inspire a serendipitous dance session or two. In the late summer, South Fortaleza, or SoFo, becomes a culinary fairground bursting with eclectic global flavors and Caribbean fare, ranging from smoky lechon roast pork to creative ceviches. Similarly in January, the ultra-local, lively three-day street party, Festival de la Calle de San Sebastían, buzzes with parades, traditional dances, food, and music.

Cruise a New Wave
Year-round small stylish eateries offer up a delightful fusion of flavors for dinner, while classic watering holes and lounges offer inventive cocktails and of course, new spins on pina colada. There’s also a new generation of artists and gallery owners fueling the island’s burgeoning creative scene. On most Tuesdays, some 20 venues stay open late in Old San Juan for the Noches de Galerias gallery crawl. See works from celebrated Latin American and global artists, including sculptures, paintings, and photographs, housed in historic gallery spaces with distinctive architectural details like arched halls and backyard patios with fountains. After gallery-hopping, many resident art lovers crowd into popular nightspots for a party that continues well into the night. In contrast to the old town’s galleries situated in colonial buildings, just over the bridges in Santurce, there’s an emerging art and design district of up-and-coming galleries, experimental design studios, and graffiti-sprayed spaces. Away from the beach, this under-the-radar neighborhood is still making waves: Every few months, leaders of the local scene host the Santurce es Ley street fest to showcase what’s going on in the cutting-edge creative community. An artistic spirit permeates both of these creative enclaves creating a timeless link between old and new. Miles from the beachfront trinket stores and tourist shops, in Old San Juan and even Santurce, you might just find a one-of-a-kind keepsake—a locally inspired art print, a wooden handicraft, an ornamental figurine–you’ll cherish back home.

Chef Eric Ripert and designer Matthew Patrick Smyth have long been inspired by Puerto Rico. See how their favorite details and memories create an unforgettable dining experience.