Travel Destinations

Explore the Oldest European-Established Outpost in the U.S. - Old San Juan, Puerto Rico

Home of the Pina Colada


Is the icy chill of winter setting in, prompting you to dream of balmy breezes and tropical climes? Are you ready to trade in all those snowy driveways and bare-limbed trees for sunny beaches and swaying palms? look no further than San Juan, Puerto Rico. The tropical destination of your dreams awaits. Best of all? No passports or money exchange required. Just grab your regular ATM and credit cards and go!

San Juan was established in 1521. It's the oldest European-established outpost in the U.S., and a feast for the senses, a complicated and engrossing patchwork of neighborhoods that will enchant you however long you decide to linger. And there's no better neighborhood to start in than Old San Juan.

This barrio occupies a thin spit of land that juts out into the Atlantic Ocean and forms a narrow, natural port. There are trinket shops and touristy outposts galore, but it takes nothing to scratch the surface and dive into the genuinely rich cultural treasures that the gorgeous colonial borough has in store.

The streets of Old San Juan are lined with cobblestones made of iron slag, carried as ballast in the ships that sailed from Europe. The stones have a mesmerizing blue cast that adds to the ethereal quality of Old San Juan's streetscape. Colonial buildings are festooned with wrought iron balconies and embellishments and splashed with sherbet hues, meaning that even if you do nothing more than meander from one tree-shaded plaza to the next, you will be transported to a place that feels deliciously unlike home.

So, first things first: Old San Juan claims to be the home of the piña colada. And, lucky for us boaters, there's not just one place that lays claim to this infamy, but two. The first spot, Barrachina, has a lovely leafy courtyard and lubricates its creamy, frothy concoctions with Ron del Barrilito, one of Puerto Rico's longstanding, homegrown premiere rums. The second place that insists they deserve the title is the Caribe Hilton, on the outskirts of Old San Juan. There they lace their potion with a healthy dollop of Bacardi Superior. It might be your duty as an upstanding member of the cruising community to sample both versions and decide for yourself which one is best -- if not the "first."

After you've properly embarked on your Old San Juan escapade with a piña colada (or two), soak up some of the many historic sights. Don't miss Castillo San Felipe del Morro, known colloquially to locals simply as El Morro. Construction of the massive fortified site began in 1539, and you can pass a fascinating afternoon exploring its many nooks and crannies. You can also blissfully while away the time simply lolling on El Morro's enormous lawn, where locals gather regularly to picnic and fly bright, soaring kites.

The Catedral de San Juan Bautista is at the very heart of Old San Juan, a graceful 1540 structure where Ponce de Leon is interred in his eternal rest. There's also the wax-covered reliquary of St. Pio, a Roman martyr whose presence in the church speaks to Old San Juan's prominence as a colonial crossroads.

Next to the cathedral is El Convento, a 17th-century Carmelite convent that's now Old San Juan's premiere luxury hotel. The stunning arcaded passageways are themselves worth the stroll alone, but if you find yourself in need at this point of another piña colada, there's no better place to indulge than the hotel's tranquil courtyard.

To pick up something to take home, avoid the shops hawking shot glasses and refrigerator magnets, and head to La Calle, where you can find a selection of caretas, the vividly painted and delightfully gruesome masks traditionally worn by revelers during the pre-Lenten bacchanal of carnival. The shop Eklektika is an excellent source for all manner of authentic handcrafts, including the hand-carved figures of saints traditionally known as santos. Hecho a Mano is a stand-out boutique for one-of-a-kind accessories and clothing.

For dinner, Calle Fortaleza is a must. The street has emerged as the go-to spot in Old San Juan for unbeatably hip and enticing restaurants. Marmalade is helmed by a New York City-trained chef and popular for its cutting-edge dishes and sleek, candy-colored decor. Dragonfly has become a standby for its small-plates menu and sexy, atmospheric interiors.

If you only have the time -- or the energy -- to hit one nightlife spot, make it the Nuyorican Cafe, hands down the most consistently reliable spot to catch the island's irresistible and exploding salsa scene. The entrance is nestled into one of San Juan's back streets, and the sound of congas, cowbells and horns explodes through the doorway. It's a resolutely locals' place that embraces any wandering turistos who might stop by. Sip a cocktail and take in the scene, or hit the dance floor to try out your moves. Things don't really get going until around 11 p.m., so be patient -- you won't be disappointed.

Old San Juan is just the tip of the tropical iceberg when it comes to greater San Juan's enormous allure. So tell us what you think. If enough of you want to head back to the destination for further adventures, we'll cover the best of the rest that the contemporary city of San Juan has to offer in a future article.

For now, happy cruising, and buen viaje!

Where to Dock

  • Club Nautico de San Juan (787-722-0177) is a European-style yacht club offers 117 slips for vessels up to 250 feet along with in-slip diesel services. It's located just across from Old San Juan.
  • San Juan Bay Marina (787-721-8062) is located in San Juan at the entrance to Old San Juan and right next to Isla Grande Airport. This marina offers 200 slips, satellite TV, 24-hour security and 10% off transient dockage to Cruising Club members.

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