While every street of Old San Juan is bedecked for Puerto Rico's favorite holiday, the Governor's Mansion (La Fortaleza) may be the most splended address of all. Originally built as a fortress, this part of the city later became the governor's residence. The mansion (shown here) is the oldest governor's mansion still in use in the Western Hemisphere.
Walking the streets of Old San Juan is a constant source of delight, given its rich architectural heritage. Every corner reveals new wonders and vistas.
Each block in Old San Juan reveals another brilliant burst of color, not to mention decorative touches, such as these marionettes.
The streets of Old San Juan are as picturesque as the technicolor rows of buildings, paved with the city's famous (and historic) blue cobblestones.
The fascinating blues of Old San Juan's cobblestones have their origin in metals. Originally made in England and containing iron ore, the stones made their way to Puerto Rico, like many cobblestones, as ballast in ships. The iron gives the stones their color, which shifts depending on the heat, sun, and humidity. It's a never-ending show.
San Juan is experiencing a true culinary revolution, and José Santaella's eponymous restaurant, Santaella, in the trendy Santurce neighborhood, is one of the restaurants leading the charge. Santaella has embraced and subsequently utterly transformed traditional Puerto Rican fare. His restaurant also houses one of the city's most popular, and sophisticated, bars.
One of the chefs at the leading edge of Puerto Rico's culinary revolution is José Santaella. Celebrated chef Eric Ripert recently wrote the forward to Santaella's cookbook, Cocina Tropical: The Classic & Contemporary Flavors of Puerto Rico, and is a frequent guest at the chef-driven restaurant.
Traditional Puerto Rican Christmas fare includes lechon (roasted pig), pasteles (vegetable paste steamed in a banana leaf), and arroz con gandules (rice with pigeon peas). Here at Casita Miramar, the hearty fare gets lighter, but no less delicious, preparations.
Coquito, rich and laced with rum, is Puerto Rico's eggnog, and each restaurant and bar does it slightly differently. Here at Casita Miramar in San Juan, it's light and potent.
One of Puerto Rico's most storied (and beloved) chocolate makers, Cortés, helms Casa Cortés ChocoBar, an addictive bar and restaurant in the center of Old San Juan. Don't miss the signature hot chocolate (shown here), and ask for the traditional treat of cheddar cheese atop a small bar of chocolate. The churros are worth a trip alone. The hallways are lined with historic chocolate molds and archival photographs, and upstairs, the family has a stunning collection of contemporary art.
Street food is always a pleasure, and vendors at the weekend farmers market in Old San Juan offer super-fresh and delicious takeaways.
For one of the most authentic Puerto Rico holiday experiences, take a short drive into the mountains outside San Jose to La Ranchera Lechonera in Guaynabo, where suckling pigs roast on open coals, and the Ramos family will package you up a holiday meal just like the ones enjoyed by local families throughout the region. If you're able to stick around the open-air facility and eat your holiday feast, you might end up with a cold local beer to drink as well. 787-789-4706.
While patriarch Apa Ramos prepares hundreds of roast suckling pigs using a proprietary family recipe, the second generation helps package up and sell to the hundreds of Puerto Rican families that line up at La Ranchera Lechonera for the days leading up to Christmas (and on Christmas Day as well).
There's a fierce battle in San Juan over where the piña colada was invented, and Barrachina, the festive courtyard restaurant and bar in Old San Juan, is one of the two spots that lays claim to the origin of the classic tropical cocktail (the other is the nearby Caribe Hilton). The popular bar sells as many as 1,200 piña coladas on a Sunday, and is worth a stop to taste a bit of history. Ask for a float of Ron del Barrilito, a rum available only in San Juan.
Puerto Rico is experiencing a coffeehouse boom, and local growers are regaining a foothold in the business. At Café Don Ruiz in Old San Juan, the artisan approach is in full evidence, from decor to site-roasted, single-source beans from this heritage producer, and six different brewing methods. There's also a small, interesting coffee museum in the buildling.
Evidence of Puerto Rico's reassertion of its coffee heritage is in the handiwork of Cafe Don Ruiz's Josué Pizarro, who recently won an international barista competition.
When in Puerto Rico, find the best hat (and it should really be a Panama hat). Smart travelers know to head to the famous (and deservedly so) Ole Curiosidades in Old San Juan. Let the remarkable staff help you choose the right brim for your style (and budget), and then customize it perfectly for you.
Master Panama hat purveyor Guillermo Cristian Jeffs's tiny shop, Ole Curiosidades, in the center of Old San Juan, has been a wellspring of style for more than 40 years. While the hats known as Panama hats are actually made by hand in Ecuador, Jeffs imports them and customizes them for every customer (including many celebrities passing through) on vintage blocks and with time-honored tools. The prices range from $40 to $1,000.
An intimate emporium of high-quality Panama hats, arts & crafts, traditional masks, and cigars, what may set El Galpón most apart is its marvelous collection of carved santos (saints), including the heralded three kings of the holiday season. The owners work with some of Puerto Rico's finest artisan carvers, who create new iterations of the kings (shown here roasting a traditional Christmas pig and also playing some drums) every year, making the shop a favorite of collectors. Located practically across the street from the cathedral, it's right in the heart of the city.
Designer Aaron Stewart's namesake boutique, Aaron Stewart Home, in San Juan is a hunt-and-gather destination year-round, but at the holidays, the shop goes all out with bold gestures of holiday cheer.
At Aaron Stewart Home, traditional expressions of Puerto Rico's love of Christmas get knowing, old-fashioned treatments, like these tea towels for entertaining.
"When I was a boy, I loved seeing all the San Juan shop windows decorated for Christmas," says Fernando Rodríguez (seated), owner with Aaron Stewart (standing) of Aaron Stewart Home. The two love recreating that childlike magic in their own boutique, where a dreamy snowfall in the windows draws pedestrians--particularly children--all day long.
In the heart of Old San Juan, this 16th-century cathedral (the second-oldest in the Americas) is always a center of the city's life, and houses the tomb of explorer Juan Ponce de Leon. That said, it's particularly breathtaking during the holidays. Check the schedule of services over Christmas, which includes a Mass that's televised live throughout Puerto Rico.
The Mercado Agrícola Natural (farmers market) every Saturday in Old San Juan draws small farmers, who bring splendid and colorful fruits, vegetables, and breathtaking flowers. Musicians tend to hang out and perform, and street food vendors bring fresh empanadas and other treats.
A no-miss excursion is this colonial cemetery, with stunning marble monuments and sweeping views of the Atlantic Ocean. The cemetery is located outside the walls of Fort San Felipe del Morro fortress, one of the island's most famous landmarks, and well worth several hours of exploration.
Not only does night life in Old San Juan hum with bars and restaurants, it includes lively and welcoming arts venues. The Poet's Passage, a bookstore, arts emporium, cafe and performance space, stages regular live readings in its vaulted, beautiful space.
Just a half-hour outside the city, paradisiacal beaches stretch for miles along Puerto Rico's northern coast. This beach, Playa Aviones, is double blessed, as it's near a string of fantastic open-air restaurants that make fresh fritters and other classic treats.
Just outside of San Juan, the town of Piñones is called the Fritter Capital of Puerto Rico, and it's a delicious day-trip. While you can check the stands out on your own, Spoon Food Tours runs an incredible tour of the area, with stops at the very best spots. In fact, check out all the tours run by this dynamic, local couple with deep connections in the culinary community.
O:live Boutique Hotel is a charming European hideaway in San Juan's Condado district (a quick drive from Old San Juan), with an excellent in-house restaurant and a rooftop bar with views of the water. Each room has an artistic individuality, such as a guestroom's breakfast nook, shown here. Rates start at $209; oliveboutiquehotel.com.