I Went to San Juan, Puerto Rico, for the First Time; Recommendations

My sister and I stayed within walking distance of Condado Beach, so visiting was a daily activity on our itinerary. We enjoyed watching everyone swim, tan, and hang out in the sun.

The beach is also close to lots of shops and restaurants, which I liked stopping at during the day.

I also highly recommend trying a treat from The Crazy Pineapple, a vendor on the beach. I paid $20 for an amazing mix of sorbet and rum inside a pineapple.

Old San Juan is a charming section of the city that dates back to the 16th century, complete with cobblestone streets and plenty of colorful buildings.

We loved looking at the architecture and stopping into different clothing, jewelry, and souvenir shops. During our visit, art vendors even lined Paseo de La Princesa, a picturesque promenade through the area.

One of our favorite restaurants in Old San Juan was Barrachina, which claims to be the birthplace of the piña colada. We each paid about $12 for our drinks, which were delicious and creamy. I thought it tasted better than any other piña colada I’ve had.

My sister and I had so much fun in Old San Juan that we came back multiple times throughout our trip.

Old San Juan is also home to historic forts like Castillo San Felipe del Morro and Castillo de San Cristóbal.

For just $10, I gained access to both sites, but due to time constraints, I was only able to visit San Cristóbal. As someone who appreciates learning about history, I loved exploring the tunnels and looking at the weaponry, wall drawings, and barracks.

I also recommend stopping by La Puerta de San Juan (the San Juan Gate), a bright red gate that was once the entrance to Old San Juan. There’s no entrance fee, and it’s located right by the water. It provided a glimpse into history and was a good spot to take photos.

Not only is Old San Juan an incredible place to sightsee during the day, but it’s an amazing place for nightlife, too.

My sister and I splurged and spent $60 each to participate in the Old San Juan Bar Crawl.

Our group had about 30 people, and we were taken to several different bars, each of which provided a welcome drink. We also got access to an open bar for around 45 minutes at one of the locations.

La Placita de Santurce is a market square that transforms into a party when night falls. When we visited, music was blaring, the streets were filled with people dancing, and there was a line to get into most of the bars, restaurants, and clubs.

We enjoyed the music and the people at Aguardiente Bar and Tulum La Placita. When we visited, neither spot charged a cover fee, and each of our drinks cost about $15.

We also had a great time at Jungle Bird, a cocktail bar that, in my opinion, had a quieter vibe than some of the other places we’d been to.

On our last full day of the trip, my sister and I decided to take an Uber to Luquillo Beach, which is about an hour away from San Juan. It cost roughly $71 to get there and back.

At the beach, we enjoyed cooler water with fewer waves and the nearby Luquillo Kiosks, a street filled with food, drink, and souvenir stands. My sister and I tried tacos from one of the vendors and were impressed by the flavors.

We noticed that beachgoers also had the option to sign up for activities like jet skiing or kayaking, but we opted to just set up a picnic on the beach instead. It was great soaking up the sunshine before heading home.

In my experience, San Juan provided the perfect mix of beaches, history, food, and nightlife without a giant price tag.

I’m still dreaming about the waves at Condado Beach and sipping on piña coladas, and my sister and I are already talking about returning.

This story was originally published on June 18, 2025, and was most recently updated on December 2, 2025.