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New Twist on the Old City

History’s anything but old news at these five San Juan, Puerto Rico institutions.

Hotel El Convento Puerto RicoHotel El Convento

Hotel El Convento
Take in some of the best views of old San Juan’s bright colonial architecture, including La Fortaleza, the city’s massive 16th-century fortification, from the rooftop dipping pool of this Carmelite convent-turned-boutique property. Though the space was once home to cloistered nuns, there’s nothing ascetic about the modern experience. Elegant period decor, from Andalusian tile to handcrafted mahogany furniture, meets modern conveniences like free Wi-Fi and superplush slippers and robes. Bonus: The 58 well-appointed guest rooms flank the lush inner courtyard restaurant, Patio del Nispero, which dishes up the best al fresco eggs Benny in town.
100 Calle del Cristo, 787-723-9020

Restaurant 1919 Puerto Rico1919 Restaurant

1919 Restaurant
Ocean to table has never had such a short distance to travel. Chef Juan José Cuevas’ well-placed dining room at the Condado Vanderbilt Hotel overlooks a seemingly endless expanse of sea. (The room itself features masculine dark woods offset by bold upholstery, like the zebra accent chairs.) Chef Cuevas draws on his Puerto Rican heritage as well as a love of locavorism, honed at New York’s Blue Hill Restaurant (with stints in several Michelin-starred kitchens along the way). Standout dishes include shrimp and sepia fusilli and tropical hamachi-fluke crudo with pineapple and avocado. The Spanish Revival property – San Juan’s first luxury hotel – was built by the same architecture firm responsible for Grand Central Station.
Condado Vanderbilt Hotel, 1055 Ashford Ave., 787-724-1919

This blink-and-you’ll-miss-it hat shop, tucked between two souvenir stores on Calle Fortaleza, is big on service. The hats – classic, expertly woven panamas in a seemingly infinite variety of sizes and price points – are fitted to your head by hatter/proprietor Guillermo Cristian Jeffs, who will glue your choice of coloured ribbon to the band while you wait and give you a history lesson about the sombrero Panamá while he’s at it. Browse while you’re waiting; the small space is overstuffed with antiques, artworks and oddities. (You can purchase vintage photographs and handicrafts like religious Santos dolls here as well.)
105 Calle Fortaleza, 787-724-2445

La Taberna Lúpulo
The heavy wooden doors that lead into the colonial-style bar are centuries old, but the craft beer scene could have been transplanted from any major North American city. Over 50 draft brews share wall space with small-batch IPAs, including domestic microbrewery Dacay’s ale and European imports. If you’re in the mood for something less sudsy, opt for the fully loaded Bloody Mary. (Yes, that really is a strip of bacon and fried pickle garnish.) Don’t worry about staying out too late either. Their hangover-brunch spin on Puerto Rican classics – think batata biscuits with chorizo gravy, migas with black beans and ancho-chili crema – is the cure for all that ails.
151 Calle San Sebastian, 787-721-3772

Escuela Artes Plasticas Puerto RicoA painting class at the School of Plastic Arts 

Escuela de Artes Plásticas de Puerto Rico
Creativity and madness are said to go hand in hand, so it is fitting that the School of Plastic Arts of Puerto Rico is housed in a former madhouse (El Manicomio Insular). In addition to offering bachelor’s degrees in art education, design, painting and sculpture, the E-shaped colonial building, with its double courtyards facing the ocean, features an impressive gallery space. The site plays host to rotating displays from the various departments – fashion shows, print exhibitions and film screenings – as well as lectures, conferences and solo shows from visiting artists and faculty. 
Antiguo Manicomio, Sala de Exhibición, in front of Castillo San Felipe del Morro, 787-729-0007



Getting There

Air Canada offers seasonal nonstop service from Toronto to Jan Juan, Puerto Rico twice a week.

Comments… or add another


Monday, January 6th 2014 23:07
Sounds and looks good... Can we do this on a cruise and stop at some of these places???
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