Word of Mouth: San Juan

Puerto Rico and its bounty of historic sites, stunning coastlines and friendly locals

This slideshow requires JavaScript.


As soon as you touch down in San Juan, warm vibes greet your face. From the sun beaming down to the super hospitable locals, Puerto Rico’s capital is a refreshing welcome to anyone escaping the winter doldrums or seeking to learn more about the city’s historic port, which was once the main gate for entering the New World.

Americans don’t even need a passport to visit this munificent Caribbean island and that, combined with the number of direct flights jetting from the US to San Juan makes it a tropical breeze to get to. That also makes it easier for criminals as well, and the island is struggling with people using it as a way to transport drugs from Mexico to the mainland. But last November, for the first time ever, the US territory voted for statehood. Even if Congress doesn’t change its status, the natives do hope for stronger military support to keep their beautiful island safe. We saw evidence of this, with a surplus of armed police officers manning the streets at all hours.

That said, there is so much local goodness to absorb all over the small island of Puerto Rico. If you’re short on time or just there for the weekend, here are our picks for making the most of stimulating San Juan.


Olive Boutique Hotel

San Juan has no shortage of high-rise hotels boasting massive communal spaces and buzzing casinos, but travelers seeking a more laid-back and well-designed place to rest their heads should look to the Olive Boutique Hotel. The Mediterranean-inspired, 15-room hotel is just a short block from Condado Beach, where you can swim in the bath-warm, sparkling blue water or lay in the sun with a piña colada in hand until the buildings cast a fair amount of shade over the sand in the later afternoon.

Head back to Olive, where you can swim in the petite rooftop pool—the backdrop to an ultra-comfortable bar and lounge area—or dine at Oliva, the hotel’s rustically stunning restaurant. At the helm is chef Nicolas Gomez, who serves fusion dishes inspired by the owners’ trips to Spain, France, Italy and Morocco, which you can savor in a wood-walled space with ceilings two stories high. The hotel’s intimate atmosphere and detailed decor is thanks to the young and highly attentive couple who run the newly opened hotel, which was formerly a small commercial office building. Forced to create at least 15 rooms to qualify as a hotel (a law in Puerto Rico), they show their talent for design by outfitting the communal areas as well as the NYC-sized rooms with furnishings that play with scale and amenities made to pamper.

Book a room at the Olive Boutique Hotel from Mr & Mrs Smith, rates start around $180 per night. Image courtesy of Mr & Mrs Smith.


Rent the Bicycle

The fastest way to get around is on two wheels, and the city’s bike lanes make it easy to navigate the 2.5 miles from Olive to Old San Juan. Rent the Bicycle is a really convenient service to do so. They will bring a one-speed cruiser to your hotel, have you sign a waiver and pay for the day—which includes a helmet and bike lock—and then they come back the next day to pick it up. They also offer bike tours for anyone seeking safety in numbers. This sustainable mode of transportation beats out the heavy traffic, while also allowing you to go off the beaten path and stop anytime for pictures, which you’ll want to do while riding along the the rugged coastline. The bike paths lead you right into the historic area, and you can ride right up to the numerous World Heritage sites and eventually back down around the other side, along the water by the formal gates to the old city.

Rates for Rent the Bicycle are $27 for an entire day; find them online or ask the hotel to set up a reservation. Image courtesy of Rent the Bicycle.


La Taberna Lupulo

Beer is the business at La Taberna Lupelo, but they also serve up a menu of gastronomic grub, including a cheeseburger pattied in house, made from chorizo, bacon and beef and topped off with a pesto aioli. The extensive roster of beers on tap include pints by local micro brewers like Dacay, whose IPA, Red Ale and Golden Ale along with choice craft beers from around the world. Wash it all down sitting at the bar or out back on their sun-drenched, graffiti-laden patio. An added bonus—the music and the bartenders are both excellent, and reason enough to spend even more time at this casual joint on the corner of one of Old San Juan’s cobblestone streets.

La Taberna Lupulo is located at 151 Calle San Sebastián. Burger and a beer will set you back about $12.


El Batey

New Yorkers missing the glory days of CBGB will love El Batey—this bar curiously keeps an authentic East Village atmosphere but lacks any pretentiousness, keeping you focused on the tropical getaway at hand. Mingle with mellow locals, keep it classic with a can of Medalla or a rum and coke, and know you’re going to pump at least a fistful of cash into the jukebox, which throws out rare and well-known tunes from the golden eras of jazz and rock.

El Batey is located at 101 Calle Cristo and open late.


La Isla del Encanto

In a large plaza that was once a military barracks, you can catch a 15-minute, site-specific film that literally highlights both the Spanish Colonial architecture of the buildings surrounding the space as well as the rich history of Puerto Rico. The newly opened production—shown in English or Spanish—is the brainchild of Tony Miceli, who used his talents in 3D projection mapping to create this imaginative performance called La Isla del Encanto. Future site-specific shows will include concerts and all types of cultural happenings.

La Isla del Encanto runs four times a night during the weekend at the interior plaza of the Cuartel de Ballajá; shows are free.

See more images in the slideshow. All photos by Karen Day unless otherwise noted.