Staying in Old San Juan vs San Juan Puerto Rico

Takeaways From Our Trip to Puerto Rico

We avoided flying during the pandemic and took our first “real” vacation in years to Puerto Rico, a direct flight away and no wait in customs lines.

Paradise without a passport.

Puerto Rico is a safe, fun place where you can drink the water, use your U.S. dollars and enjoy its many lovely public beaches for free.

We flew into San Juan and rented an apartment in the old part of the city for a week, venturing outside the city for excursions.

It was my first visit to this U.S. territory, and I knew little about it beyond the images of desperation burned in my brain from news reports of hurricanes and power outages.

What I found was a joyful place with friendly people, gorgeous natural beauty, historic architecture, and wonderful food that’s still recovering from past hurricanes and the pandemic.

A great (but not cheap) spring break destination

Dining in one of the many good restaurants in Old San Juan. Photo credit: Hunt & Peck Blog

I thought Puerto Rico would be more affordable than our last tropical vacation at a fancyish resort in Playa del Carmen, but that wasn’t the case.

Because we traveled in prime season – the first week of April that included our son’s spring break and the Easter holidays – our flights were pricey at $833 each. On a budget airline, no less. 😒 If only we could have waited a few weeks, we would have saved a bundle: I saw direct flights for less than $200 in May! We did save some serious money by buying these bags to avoid paying extra for luggage. 😊

But it was a great time to visit.

Unlike Mexico this time of year, there were no rowdy spring break crowds. The tourists were mostly families and couples. The younger people we saw seemed to be there to enjoy the food and culture like the other tourists.

And it wasn’t crowded. Even when the cruise ships came into port, dumping hundreds (thousands?) of people into the town, we got around easily and didn’t wait in lines.

We did have some rain (more on that in a bit), but on the whole, the weather was great, with temperatures from 75 to 85 degrees. Puerto Rico enjoys a moderate climate, so this is basically the range at any time, although August tends to have a lot of rain, and hurricane season lasts from June to November.

The food in San Juan cost more than we expected but was worth it. We ate all but two meals in San Juan restaurants. Each one was tasty, and some were super delicious. Our favorite foods were Puerto Rican specialties new to us: mofongo, a common side dish made of fried, mashed plantains, and limber, a sweet treat served in a plastic cup that’s somewhere between a popsicle and Philly water ice.

limber shop in Old San Juan
Buying a limber in Old San Juan, Puerto Rico. Credit: Hunt & Peck Blog

On the flip side, we felt like our apartment was a steal. It could not have been in a better location: on a quiet street walkable to all the sights and shops, with a gorgeous view from a large rooftop terrace.

We paid around $250 a night for the apartment, which had a full kitchen. This was on the higher end of VRBO rentals in San Juan; housing on the whole was much less than we expected.

We loved staying in the old part of the city … so many unique places in historic buildings dating back to the 16th and 17th centuries.

You can get a good sense of the properties by looking through the rentals that are available.

San Juan vs. Old San Juan

San Juan is the second oldest city in the Western Hemisphere and has a lot to offer.

Where you stay in San Juan really depends on what kind of vacation you’d like. The fact that one city can accommodate so many different types of vacations is pretty amazing!

Old San Juan, with cobblestone streets and brightly colored buildings adorned with decorative gates, oozes old-world charm. It bustles with restaurants, museums, and shops and is close to some of the island’s top beaches. It’s highly walkable and the place to be if you’re looking for something more than a beach vacation.

cobblestone street in Old San Juan, Puerto Rico
Bright buildings and brick streets of Old San Juan. credit: Hunt & Peck Blog

Except for the fact that it borders the ocean, the rest of San Juan is a typical, modern city with skyscrapers, condo buildings, and paved streets.

The resort hotels in San Juan’s Condado neighborhood dot the shore, including the Caribe Hilton, which claims to have been the spot where the pina colada was invented.

If you’re looking for more of a chill, sit-on-the-beach vacation, Condado would be a great spot, and some of the city’s top sights in Old San Juan are a quick Uber or scooter ride away.

Speaking of that, the top tourist destination in San Juan is El Morro, a massive fort built in the 1500s to protect San Juan from attack by sea. Puerto Rico was the first major island in the Caribbean that European explorers went to en route to the Americas from Europe.

View from El Morro Fort in San Juan, PR
The views from El Morro are incredible!

El Morro is a great place to learn about San Juan’s history. Real quick ….

In the age of New World exploration, Puerto Rico was the gateway to riches in the Western Hemisphere, with El Morro being the barrier Spain built to keep other countries out. The English and the Dutch, specifically.

Spain controlled Puerto Rico from 1508 to 1898, and the wealth it amassed from the Americas – gold, silver, spices and furs from Mexico and Central and South America – transformed it into a world power. (In Spanish, Puerto Rico translates to “rich port.”) Under Juan Ponce de Leon, Spain attacked the native Taino Indians. Over the decades that followed, the Tainos and their culture were all but wiped out.

Puerto Rico became a U.S. Territory in 1898 following the Spanish-American war – which was fought in Cuba.

Beyond San Juan

Being first-timers, we thought it was a good idea to book some guided tours that, in our past vacations, have been a fun way to get to know a new place.

Our excursions included an evening kayak through San Juan, snorkeling in the bay, and our favorite, a tour of the El Yunque Rain Forest, where we hiked, used rope swings to jump into swimming holes, and slid down “natural waterslides” (giant rocks that were somehow not uncomfortable).

El Yunque is worth a visit. In addition to hiking and swimming, you can see waterfalls, native plants and species and take in awesome views. You can also zip line and ride ATVs in the foothills.

We enjoyed our excursions so much, we set out to find more fun on our own.

We searched “things to do outside of San Juan” and decided to drive to Ponce, Puerto Rico’s second biggest city which came highly recommended.

The drive took us straight through the middle of the country on a winding highway through mountains that dwarfed the clusters of colorful concrete houses below them.

While Ponce topped many must-see lists online, the drive there ended up being the highlight for us.

Our first stop in Ponce was La Guancha Beach. We’d read about the free parking, boardwalk, and food kiosks and planned on getting lunch.

The sun was out when we arrived, but the vendors weren’t: we were told they packed up and left for the day after a hard rain the morning. It was like a ghost town. The few visitors seemed to be wayward tourists like us.

We headed to the main town square to find something to eat. We found many empty buildings and only a handful of businesses open on a Thursday afternoon. The meal we had overlooking the square was the only disappointing one we had in Puerto Rico, at a Mexican restaurant that put fries in the burritos! 🤔

Rainy days were a challenge

Rain presented the biggest challenge for our Puerto Rican vacation. We were expecting some rain and had packed our raincoats, but when we ventured out in the rain – or after a rain – we found many things were closed, including in San Juan.

And morning rains kept some businesses closed all day, long after the clouds cleared. Rain was forecast almost every day for the last half of our vacation, and that really put a dent in our plans, even though the rain never lasted a full day.

I’m not sure what the people who came to Puerto Rico to sit on the beach did on those overcast days!

Getting around the island

Unless your rental comes with parking, you don’t want to have a car in San Juan. Parking is tight and traffic is fierce, especially in Old San Juan, but luckily there are lots of other options.

We used scooters, Uber, and our feet to get around. The car we rented cost $80 for the day.

I’d read about a trolley that used to serve San Juan, but it was out of service during our visit.

The vibe was carefree

A run-down building in Old San Juan.

I found Puerto Rico to be laid back, fun, and a little rough around the edges. One woman I spoke with said the pandemic did more harm to the island than the last big hurricane, which shut down businesses for years.

It’s both beautiful and unkempt. Not all of its messes have been cleaned up, and life goes on around them.

Even in the toniest neighborhoods, you will see $3 million homes next to abandoned properties. Junk cars, abandoned properties, and trash are common sights that, against the stunning ocean backdrop, don’t detract much from the overall picture.

Puerto Rico wears a smile despite its struggles, and its people are proud.

What I’d do differently next time

My biggest piece of advice about visiting Puerto Rico is, unless you’re a beach lover, you don’t need a whole week here.

Vacation time is precious, and we felt we could have cut our trip short and still gotten to experience a lot of what it has to offer: history, culture, delicious food and natural beauty.

I hope that doesn’t sound like a criticism. We loved Puerto Rico and hope to return soon, maybe for a long weekend with a cheaper flight, and definitely not in the rainiest month of August.

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4 thoughts on “Takeaways From Our Trip to Puerto Rico”

  1. Hi Rich, Alice and Marco,
    What a great holiday you had! PR is one of my favorite vacation spots . Thank you for your stories.

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