The Perfect Weekend Getaway? It Might Just Be Puerto Rico

A photo of the street view of Old San Juan in Puerto Rico.
Rainy day in Old San Juan; outside Barrachina, which claims to have invented the piña colada. Photo courtesy of Susan Shain

When you’re wandering around Old San Juan, you’ll feel worlds away from the United States.

Quaint cobblestone streets. Murmurs of Spanish. Centuries-old fortresses.

But the capital of Puerto Rico is just a few hours by plane — and because the island is a U.S. territory, you won’t need a passport to get there.

You can also use your cell phone and spend U.S. dollars, and since almost everyone speaks flawless English, you won’t need to worry if you don’t speak Spanish (though most people will happily let you practice).

I recently spent 10 days in this tropical paradise. It makes a perfect weekend getaway for Americans seeking exotic sights, sounds and tastes without having to travel far from home.

What to Expect

As you probably know, Puerto Rico was devastated by Hurricane Maria in September 2017. The storm caused $90 billion in damage, according to the National Oceanic and Atmospheric Administration. Many residents went without power for almost a year.

Given all the negative news coverage, I wasn’t sure what to expect. What would it look like? Would there be hot water and electricity? Would restaurants and hotels be open?

When I hopped off the plane, I was surprised to see that San Juan looks, well, normal. Restaurants, hotels and attractions are open, and the city has been welcoming cruise ships for months.

I’m not saying the work in Puerto Rico is done. It is $71 billion in debt, and the island faces myriad challenges. While I hope you’ll take some time to learn about the territory before visiting, that’s not what this article is about.

So, instead of diving into Puerto Rico’s politics and history, I’ll just assure you: The average tourist can have a perfectly lovely visit.  

And you should, because one of the best ways to support the island is to spend money there. Puerto Ricans are some of the friendliest people I’ve encountered in my travels; they will likely welcome you with a smile.

When to Go

A photo of Old San Juan in Puerto Rico.
A view of Old San Juan in Puerto Rico. Photo courtesy of Susan Shain

The temperature in San Juan is around 75 to 85 degrees year-round.

High tourist season lasts from mid-December to mid-April and comes with bigger crowds and prices. Spring’s shoulder season (mid-April to June) has fewer crowds.

It’s hurricane season from June to November, though that shouldn’t necessarily deter you from visiting. The weather can still be great, and you can find discounted rates on hotels, according to U.S. News & World Report.

What to Do

You won’t find yourself hurting for activities while visiting San Juan. Here’s a sampling of offerings in this historic seaside town.

Old San Juan

For most visitors, simply wandering the charming streets of Old San Juan could provide days of entertainment.

With 16th- and 17th-century architecture, swaying palm trees, blue cobblestones and stray cats sleeping on stoops, you’ll feel far removed from big-box stores and strip malls.

Stop into stores, sit in one of the many plazas, grab a cup of world-class coffee from Cuatros Sombras and watch the world go by.

Museums and Attractions

History lovers, rejoice! San Juan’s museums are incredibly affordable.

Entrance to the San Juan National Historic Site, which includes the 16th-century El Morro Fort and Fort San Cristóbal, is $7. La Casa Blanca, the oldest continuously occupied house in the western hemisphere, costs just $3 to enter.  

Ready to spice up your day of history? Take a $15 historical tour of the Bacardi rum distillery.


A view of the water taken in Puerto Rico.
Hundreds-year-old walls surrounding San Juan. Photo courtesy of Susan Shain

When it comes to beaches, you usually have to get out of the city to find beautiful ones. But that’s not the case here.

Neighborhoods like Condado, Ocean Park and Isla Verde all have pristine beaches and are just minutes from Old San Juan. Many visitors choose to book waterfront hotels here.

But even if you don’t stay by the beach, set aside at least a half day to enjoy the sun, surf and white sand while pretending you’re in a Puerto Rican postcard.

Day Trips

To get out of the city, the most budget-friendly option is to rent a car. (When I looked, it was only $17 per day.)

You can then cruise 30 miles to El Yunque, the only tropical rainforest in the U.S. Most of its trails closed after Maria, but they’ve been steadily reopening. Even so, you can always take in its lush surroundings and waterfalls.

On your way back, hit up Piñones, a beachside town famous for its laid-back food kiosks.

Where to Eat and Drink

A photo food sitting on a table at a restaurant in Puerto Rico.
Tray of croquettes from La Croqueteria, one of the kiosks at Lote 23. Photo courtesy of Susan Shain

Although you don’t hear about it as much as other foodie destinations (yet!), Puerto Rico’s culinary scene has got it going on.

Its most famous dish is “mofongo”: garlicky fried plantains, sometimes shaped into a bowl and filled with meat and broth. You can find it anywhere from hole-in-the-wall establishments to fine-dining restaurants.  

As far as budget options go, here were a few of my favorite spots:

Lote 23: This industrial lot is filled with over a dozen food kiosks — it’s an absolute must visit. Be sure to try manchego croquettes at Croqueteria (two for $4) and homemade cashew milk lattes at Cafe Regina ($7). El Jangiri’s poke bowls ($8-$12) are also excellent.

La Bombonera: One of the oldest restaurants in San Juan, this bakery has been open since 1902. Its most famous offering is the “mallorca”, a flaky pastry filled with cheese and topped with powdered sugar ($3.95). Yum.

Café Manolín: Stop by this unpretentious local joint to sample chicken mofongo ($10.95) and “empanada de lomillo”, or breaded beef steak ($11.95).

Señor Paleta: In San Juan’s tropical climate, you’ll probably get a hankering for something cold. This gourmet popsicle shop has a range of inventive flavors; my favorite was Nutella-filled strawberry ($4).

Barrachina: This restaurant claims to have invented the piña colada. Although another bar in the area claims it, too, all you really need to know is the piña coladas here ($8) are delicioso. Sit at the bar in the courtyard, and you’re guaranteed to have a good time.

La Placita de Santurce: For a fun night out, grab a beer ($2) and wander around this lively bar area, where the streets fill with locals and tourists alike. It’s perfect for people-watching — and if you stay late enough, you’ll undoubtedly see some spontaneous salsa dancing.

Where to Stay

A hotel room in Puerto Rico.
Room at The Dreamcatcher, now called “The Gallery Suite”. Photo courtesy of Susan Shain

When deciding where to stay in San Juan, you’ll face a tough decision: old town or the beach. While Old San Juan offers plenty of charm, staying at the beach is, well, staying at the beach.

The good news is that most options are fairly close together, and by choosing one, you’ll probably only be a $5 to $7 car ride from the other.

Since Old San Juan is small, its accommodation choices aren’t as robust as elsewhere in the city. Some reasonably priced options I found were the Fortaleza Guest House and the Decanter Hotel.

You can also choose an Airbnb, but be mindful that it isn’t always best for a city’s residents.

Large, resort-style hotels abound in Condado, a touristy beach area a few miles east of Old San Juan. I’d recommend staying a little further afield, though; you’ll get more for your money, and won’t, be sleeping at a Holiday Inn in Puerto Rico.

Here are two wonderful options:

Nomada Urban Beach Hostel

This trendy hostel is located just a few blocks from the beach. It has a fabulous rooftop — complete with hammocks and lounge chairs — that overlooks the ocean. It also has a shared kitchen, allowing you to cook meals to save money.

Even though I’m past the point of sleeping in dorms, I often still book private rooms at hostels. They’re a great way to enjoy the low rates and sociability of a hostel without listening to other people snore.

Here are its nightly rates:

  • Dorm bed: $32 and up
  • Rooftop tent: $45 and up
  • Private room: $64 and up
  • Deluxe private room: $88 and up

The Dreamcatcher Hotel

This boutique vegetarian bed-and-breakfast feels like it’s out of an Instagram catalog. (I know that’s not a thing, but if it were, this hotel would play a starring role.)

Each room is uniquely decorated with vintage finds, and the grounds, filled with plants and hammocks, ooze tranquility. Rates depend on which room you book but start at $89. You can opt for fresh vegetarian breakfasts ($11) and also make use of a shared kitchen.  

How to Get to San Juan

A building view with umbrellas in the air taken in Puerto Rico.
San Juan’s Presbyterian Church on Calle Fortaleza. Photo courtesy of Susan Shain

Many airlines, including Southwest, Spirit and JetBlue, offer daily departures to San Juan. (Note that with Spirit, you’ll have to pay extra for all luggage, including carry-ons.)

When looking at flights about a month out from my trip, here are some round-trip rates I found:

  • From Chicago O’Hare: $279 (Spirit)
  • From Newark: $307 (JetBlue, direct)
  • From Baltimore: $331 (JetBlue, direct)
  • From Atlanta: $182 (Spirit)

Once you get there, renting a car isn’t necessary if you’re just staying for the weekend.

Ubers and Lyfts are plentiful and cheap — with the exception of arriving at the airport, when you’ll have to take an official taxi to your hotel. Within the city, walking and biking are great options; some hotels even offer free bike rentals.

Although you won’t get to see everything in Puerto Rico in a weekend, you can always save things for your next trip. Because, once you go — there will always be a next trip.

Susan Shain is a freelance writer and digital nomad. She covers travel, food and personal finance (basically, how to save money so you can travel more and eat more). Visit her blog at, or say hi on Twitter @susan_shain.