48 Hours in San Juan, Puerto Rico

Puerto Rico is easy to fly to from the eastern half of the U.S. – and you don’t even need a passport to feel like you’ve ventured to a foreign land. The island’s capital and largest city, San Juan, is a great home base on the island. It’s easily accessible for those wishing to head to the beach or take a road trip to El Yunque (the rainforest), but offers plenty of restaurants, nightlife and historical attractions on its colorful cobblestone streets.

photo: Chris Amelung/Flickr

It’s easy: many airlines fly directly from U.S. cities to San Juan, including affordable airlines like JetBlue and Southwest.

It’s not as far as you think: a flight to San Juan is a little under four hours from the northeast U.S.

Here’s what to do if you have 48 hours in San Juan, Puerto Rico.

Tour Old San Juan

photo: Thomas Shahan/Flickr

Walking around Old San Juan is entertainment in itself, as the streets are so picturesque with 500 years of history and tropically-colored colonial architecture. But make sure you check out the two forts, El Morro and Castillo San Cristóbal, which were used as active military forts as recently as World War II.  If you’re not up for walking a lot, there’s a free trolley to both forts that you’ll see driving by (just hop on!).

photo: Jaime Olmo/Flickr

For dinner, head to Fortaleza Street, San Juan’s “restaurant row” where you’ll find some of the city’s best restaurants. The Parrot Club is a very popular spot catering mostly to tourists, but serving a good representation of traditional Puerto Rican dishes.

Party Like a Local

Once night falls, make your way to Nuyorican Cafe, a small, packed spot that’s the best place to catch live music, let loose and dance in San Juan. A healthy mix of out of towners and locals, Nuyorican Cafe (312 Calle San Francisco) is quite hard to find, but don’t give up. My first night in San Juan, I actually couldn’t locate it and assumed it must have closed. But a few nights later, while walking around Old San Juan, we heard loud, pulsing music and followed it down an alley. Voila! Nuyorican Cafe. It’s $5 at the door to enter, but worth every penny.

Another spot in Old San Juan that’s packed with locals on weekend nights, Colmado Bar Moreno (365 Tetuan Street) has cheap drinks served in plastic cups and a nonstop bumping reggaeton playlist. It skews a bit younger here (remember that the drinking age in Puerto Rico is 18) but it’s still a good time and conveniently located steps from the taxi stand.

After all that drinking and dancing, where do Puerto Ricans go for late night eats? Los Pinos (655 Avenida Ponce de Leon, Miramar). This no frills, authentic local restaurant is open 24 hours, serving up traditional Puerto Rican and Dominican dishes along with tasty sandwiches at very affordable prices. Just don’t expect service to be quick – sit back and relax, you’re on island time!

Lounge on the Beach

photo: Prayitno/Flickr

You’ll find some of the best beaches in the Condado neighborhood of San Juan, where all the big oceanfront resorts are located. Someone will be selling lounge chairs, umbrellas, cocktails and even empanadas on the beach if you want to catch some rays. Or, for more of a social scene, rent a chair at the beachside pool of the chic La Concha resort.

Visit El Yunque

photo: Thomas Shahan/Flickr

With only two days in San Juan, it’s likely you’ll spend most of your time exploring Old San Juan and at the beach. But if you’re like me and the beach can only entertain your for a couple hours at most, you’ll want to rent a car and take the hour-long drive to El Yunque, Puerto Rico’s rainforest. A quick trip to El Yunque will only take half a day, but if you’re more adventurous, you can spend a full day hiking its more challenging trails or booking an adventure tour. If you’re going the DIY route, take Route 3 out of San Juan and travel about an hour to Route 191, which will take you into the rainforest.

photo: BluEyedA73/Flickr

For an easy but scenic hike, take La Mina trail to La Mina Falls, where you can swim in a waterfall. The hike is only 0.7 miles, and is pretty flat. Note that due to its easy access and beautiful destination, La Mina is often quite crowded.