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Why I Loved San Juan, Puerto Rico

I have terrible passport envy.

My natural tendency towards wanderlust has been made exponentially worse by reading books set in other countries, befriending other travel writers who go abroad more often than I do and scrolling through a breathtaking (and jealously-inducing) assortment of travel photos on social media this winter.

Plaza of the Religious Procession, Old San Juan, Puerto Rico

So when we had an extremely limited amount of time to arrange this year’s vacation, we landed on Puerto Rico through a rather unorthodox decision making process. We actually let fate decide our vacation.

And I’m not gonna lie, I was kind of ambivalent about it, right up until we landed in San Juan. I wanted another freakin’ passport stamp. I wanted to go abroad, to immerse myself in a different culture, to feel the rhythm of a place that’s totally different from where I live, hear another language, taste new foods. Puerto Rico is a U.S. Territory, so it would just feel like the U.S…right?

Wrong. I got all the experiences I wanted from an international getaway and more, just by exploring the capital city of San Juan. And when I wasn’t looking, I totally fell in love with the place. Here are a few reasons why I think you’ll love it too.

Isla Verde beach

Caribbean life with American convenience  The whole U.S. territory thing certainly traveling to Puerto Rico easy for U.S. citizens. You don’t need a passport. You use American money. Your cell phone will work. English is widely spoken in San Juan and other major cities. And if you forget something at home, there are a bazillion Walgreens stores just waiting to sell it to you.

But that doesn’t mean that it feels like home. Puerto Rico has an incredibly rich and diverse history that’s uniquely its own, fabulous food and a distinctly celebratory, social Caribbean vibe.

Old San Juan

Walk through history Speaking of history, Old San Juan is an absolute must-see for any history buff. The historic district is the oldest settlement in Puerto Rico (founded in the early 1500s) and still retains its colorful colonial buildings and distinctive blue cobblestone streets.

You can stroll those streets, enter through the city gates and run your hands along the historic settlement’s stone walls. San Juan’s strategic location made it an important gateway to the Caribbean and climbing the ramparts of the forts of San Felipe del Morro and San Cristóbal to gaze out at the Atlantic Ocean make this point eloquently.

San Felipe del Morro fortress in Old San Juan, Puerto Rico

If you’d rather focus on the present, check out Old San Juan’s art galleries, shops and vibrant restaurants. Or take a coffee on a shaded plaza and watch the kids splash in a fountain. The sunsets over the Atlantic along the Paseo de La Princesa promenade are especially stunning.

Families flying kites over El Morro

Skip the all-inclusives and go for immersion The most popular tourist districts — Old San Juan, Condado and Isla Verde — boast lots of bars, shops and restaurants just steps from the major hotels, so there’s really no need to take all your meals inside when you can just walk down the street and experience the local scene.

When you’ve explored one neighborhood, just move on to the next. The three tourist zones are located near each other and it’s easy to get from one neighborhood to the next via taxi, bus and car. We walked from Condado to Old San Juan, a fairly easy jaunt for most able-bodied urban explorers without little ones in tow.

Speaking of kids, San Juan (and Puerto Rico in general) are very family friendly. Children are welcome in almost every restaurant and attraction and multi-generational groups were a common sight all over town. There are established tours, water sports packages and excursions that will work for all ages. And if the thought of walking tires you out, Old San Juan offers free, hop on, hop off trolley services around the old city, which seemed especially popular with the oldest and youngest travelers.

Dusk falls on La Playita de Condado San Juan, Puerto Rico

Urban beaches — the best of both worlds Can’t decide between an urban getaway and a beach vacation? Do both. San Juan has lots of easily accessible public beaches, right within the city limits.

I loved the wide beaches of Isla Verde, where we spent Valentine’s Day relaxing between picnicking families and beer drinking Sanjuaneros who taught us a thing or two about what to bring to the beach. (The list starts with coolers and ends with a comprehensive sound system.) I also (finally!) mastered bodysurfing by putting my Spanish skills to work/shamelessly eavesdropping on a local dad who totally knew what he was doing.

We spent a leisurely afternoon drinking beer, swimming and dozing on a tiny, sheltered stretch of sand at La Playita de Condado, just east of the Ashford Avenue bridge, as the Atlantic crashed against the coral nearby. We even put our feet in the water at El Escambron, a hidden beach on the outskirts of Old San Juan. It’s just a few feet beyond a free trolley stop. I doubt the other tourists even knew it was there.

Mofongo at El Alambique on Isla Verde beach. This was one of my favorite dishes — and restaurants — overall.

Fabulous flavors Puerto Rican food is all about lovingly prepared meat, crisp, fried goodies, fresh seafood and fun flavor combinations. It’s comfort food with a Caribbean twist, hearty, filling, unpretentious food that works as well on styrofoam plates in laid-back roadside kiosks as it does in beachfront restaurants. I wrote a more comprehensive article on Puerto Rican food that I’ll link to when it goes to press, but here is the condensed version.

  1. Plantains are awesome.Whether they’re sweet and standing in for bananas in Bananas Foster or fried, savory and mashed and served with meat or seafood in mofongo (a contender for Puerto Rico’s signature dish) I pretty much want to eat them all the time.

  2. Fried food is addictive.Normally fried stuff is too heavy and greasy for me, but Puerto Rican cooks have got that crispy, flaky, flavorful combo down. Consequently, I basically ate like a teenage boy. Fried yucca, cornmeal fritters, the aforementioned plantains…I tried it all, and it was all pretty dang delicious.

  3. When it comes to seafood, think outside the filet.A simple, fresh-caught fish fillet is good. Equally fresh lobster empanadas, conch fritters, crispy codfish bites or luscious seafood soup are even better. Trust me.

  4. When in doubt, order pork.Puerto Ricans take their pork seriously.

A crazy beach hair/piña colada selfie. These are from Barrachina in Old San Juan, which claims to have invented the drink. And oh yeah, this is Derrick, who is no doubt still rolling his eyes at his inclusion in this post.

Cold drinks and salt water go hand in hand From Puerto Rican rum to piña coladas (which were created on the island), Puerto Ricans understand that there’s nothing better than a cold drink on the beach…or after a walk…or with friends…or, like, whenever. We stumbled upon a pretty rockin’ party at the gas station in our neighborhood and for $1.50 a beer, we joined right in.

I also heartily endorse coco trio — fresh coconut water served in the coconut. A vendor hacks the top off with a machete, so you get a drink and a show, all in one. It’s heaven on the beach and good for you too.

And despite my craft beer leanings, I’m now fond of Medalla Light, a weirdly addictive and (I swear to God), somehow miraculously hydrating Puerto Rican beer that locals and tourists drink like water. A guy told me (quite insistently) that I wouldn’t get a hangover drinking Medalla Light. And you know what? He wasn’t wrong.

El Yunque rain forest near Fajardo, Puerto Rico

Easy access to diverse landscapes If you get tired of urban San Juan, you don’t have to look far to find something different. Just hop in a car or take a público (public taxi) to explore scenic mountain drives, coffee plantations (Puerto Rican coffee is stellar — smooth and yummy), quiet beaches, mellow small towns and even El Yunque, the only tropical rain forest in the United States National Forest system.

The island is relatively small — just 3,492 square miles, about the size of Connecticut — so you can drive across it in just a few hours. And there’s a lot to see in those 3,492 square miles.

To give you an idea of what’s possible in one day, here’s what Derrick and I did on our last day in Puerto Rico. We spent the morning on the beach in Vieques, an island off the east coast of the main island (I’ll have more stories about that for you later), took the ferry to the city of Fajardo after lunch, explored El Yunque for a few hours, ate street food at the kiosks by the beach in Luquillo on the northeast coast and celebrated my birthday with beer and flan on a patio in San Juan before catching our flight home.

You want to go now, don’t you? Book a ticket — I’ll go too.

Fajardo, Puerto Rico

These photos were taken with a nifty Samsung Galaxy S6 edge on loan from the fabulous folks at Verizon. All opinions are my own. And my opinion of this phone is that it’s pretty cool and I loved taking photos. They seem really crisp and clear to me.  My tech-savvy husband’s opinion was equally positive, although he expressed it mainly through wide-eyed glee and swiping the phone from me whenever possible.

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