Colonial and contemporary come together in vibrant style with a capital’s historic heart

The small and the significant, the ancient and contemporary all stand side by side and often converging to produce an identity with a vibrant past around Viejo San Juan, or Old San Juan.

For its residents or those who work here, this mixture forms part of the daily landscape of their lives. For the traveller arriving for the first time or returning again, the intricate weave of different periods and worlds is central to what makes Old San Juan such a continuously intriguing exploration.

The distinct ambiance of this colonial city is also derived from its physical separation from the Puerto Rico mainland­­—being stretched across a narrow island that lies off modern-day San Juan. The city is bounded by the Atlantic Ocean to the north and to the south by the Bahia de San Juan (San Juan Bay), and there is a marked change of tempo and character as you arrive across one of the three connecting bridges from the busier and broader avenues of the new city and into the narrower, often sloping and winding streets of Old San Juan. Movement and activity are certainly present along its main arteries and at commercial venues, but it all remains as a part of the living flow of the old city.

The intriguing mix of past and present might confront you in any number of ways once you arrive into this original heart of the Puerto Rican capital. That ability to reinvent itself through the transformation of every type of original structure into some new identity surfaces in almost every type of structure to be encountered here. The very fact that all of Old San Juan is a World Heritage Site certainly encourages that phenomenon. Thus, what was once a colonial era home now becomes a contemporary cafe or boutique or restaurant, an ancient fort is turned into a gleaming museum, or a former school becomes a hip boutique hotel.

The more imposing monuments may often be those that initially catch the visitor’s eye. Even here, the legacy is romantic: founded by none other than Spanish explorer Ponce de León in 1521, Viejo San Juan was early on enclosed by walled fortification that includes the vast Castillo de San Felipe del Morro, or “El Morro” Fortress. From this site built to guard the San Juan Bay, soldiers fought off attacks by both the English and the Dutch. Today, you can still explore its vast interior on guided tours, stroll its wide exterior spaces, or attend cultural events—one of which is appropriately a kite festival, a local passion which puertorriqueños enjoy here frequently. The other inescapable landmark is its sister fort to the east, the 17th-century Castillo San Cristóbal, which is also maintained by the National Park Service and allows visitors to roam its maze-like interiors and dungeons. The finest moment may be had as you stand near the top of its 150-foot walls and soak in the fabulous vistas of the old and new urban terrain.

The more personable highlights to be savoured, however, emerge in the town’s public and private spaces that allow for plentiful human interraction. So for instance, even a city square reflects the flow of centuries here: at the Plaza de Armas, the original main square once used as military drilling grounds, is now a plaza that serves as a central meeting location with its street artists and food vendors livening it up daily. The tree-lined Plaza de Colón, named after Columbus and bordered by fine and casual dining spots, is an excellent refreshment pause after visiting the adjacent fortress of San Cristóbal, while also providing a vivid picture of everyday Puerto Rican life. But, if knowing which key points of interest to include on any outing by foot around Old San Juan is essential to experiencing it as a destination, just as key to understanding its character and landscape is to allow for some random diverging along its narrower pedestrian streets while traversing the town from one point to another. If anything, Old San Juan is a vast museum of many dimensions and many actual physical levels as well—and not just within the confines of its landmark fortresses, but in its many steeply sloping cobbled streets. A series of outdoor steps leading upward on a pedestrian byway, bordered by brightly hued and balconied two-storey colonial buildings, the occasional resident enjoying the still of the afternoon by his front door, and the town’s ubiquitous cats guarding almost every doorway along the street is simply one of the truest images of Old San Juan that endures in the memory.

Of course, some of the more prominent avenues provide their own particular collection of both landmarks and present-day life. While the northern parameters of the town are dominated by the forts, the southern edge of Old San Juan brings along a splendid taste of old Europe with its broad Paseo de la Princesa that skirts the waterfront facing San Juan Bay. A stroll along this tree-shrouded promenade leads from the grey and white La Princesa, a neoclassical building originally constructed as a prison but now renovated as home to the Puerto Rico Tourism Company and also a gallery for contemporary Puerto Rican art, to its other end that leads into the Paseo del Morro, a shoreline path beneath the ciy walls. Along the way, footnotes to San Juan’s more turbulent past are commemorated in striking sculptures such as La Rogativa, a recreation in bronze of a famed procession of women that helped ward off a British invasion in the 18th century.

Other principal streets running both north and south or east to west have established themselves as focal points for dining and gallery enclaves of island arts. Food enthusiasts are frequently drawn to such dining hubs as Fortaleza Street, for instance, which is also the scene for an annual culinary event showcasing many of the area restaurants and bistros.

While contemporary Puerto Rican cuisine, or criollo nuevo, is a centrepiece of the menu at local establishments, the many worlds of Old San Juan come together again for the palate too with the presence of dining spots devoted to the best from other points around the Americas to Europe and Asia.

What to shop for locally, on other hand, could include either the practical, the pleasurable or the decorative— be it handmade cigarillos and authentic panama hats, to be found in the small shops on streets such as Fortaleza or Cristo, or authentic mementos that include the small detailed santos— handcarved saints and scenes—and the flamboyant vejigantes (festival masks).

Finally, that multi-layered texture of style and period that comprises the city is just as evident in its elegant-to-hip selection of upscale accommodation. A quintessential landmark in that category has to be the Hotel El Convento, which sits along Calle Cristo and adjacent to the main Catedral de San Juan Bautista. This former Carmelite convent was lovingly renovated in the post-war period, initially by Robert Woolworth, heir to the Woolworth fortune, to exude colonial elegance with features such as marble chessboard floors and mahogany furniture.

Today, after several more renovations, this structure of over three centuries stands as one of the most visible reinventions of identity around Old San Juan. As Robert Woolworth’s daughter Priscilla observes of its present life: “Because I’m drawn to anything sustainable, I was thrilled to hear that during the recent renovations of the El Convento, many antiques that my father had chosen locally or brought from Spain at great expense and which had been stored away, have been resurrected and returned to their original spots. Decorating with antiques is actually very eco, as those pieces are re-used, re-loved and re-appreciated by new generations.”

Also transforming older edifices into smaller boutique stayovers are the eclectic Da’House Hotel on San Francisco Street, a former national arts centre building which draws on a mix of antique and modern in its furnishings along with original artwork pieces from Puerto Rican artists, and the nearby Casablanca Hotel on Fortaleza, which as its name suggests is inspired by North African design and ambiance. Across from Da’House and not to be missed is the very special Nuyorican Cafe, which comes alive as the day winds down with theatrical and musical artists performing jazz and latin beats. While Old San Juan dreams of yesterday, its vibrancy and identity derives from its willingness to engage past with present and fuse them together to produce its own unmistakable style.

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