My Trip to San Juan in August

San Juan in August? Count me in! When we touched down, I had no idea what kind of adventure was waiting for us. But let me tell you, it was everything I hoped for and more. This wasn’t a fancy, luxury escape (who needs that all the time, right?), but rather a laid-back, fun-filled few days packed with incredible food, quirky finds, and some good ol’ wedding shenanigans.

From navigating the streets of Calle Loíza to diving into mofongo for the first time, every moment was a little adventure. And, of course, having my best friend Darien and his wife, and my wife by my side made it all the better.

Day One: Calle Loíza – Where the Fun Began

We kicked things off in San Juan by staying in one of the coolest areas—Calle Loíza. This street had it all: food trucks, local shops, and endless character. I’m talking about a vibe where you can grab a quick bite, pick up a funky souvenir, and feel like a local in no time. The best part? Everything was within walking distance, so we spent the day wandering around, soaking in the atmosphere. At one point, Darien even found a local barber shop and managed to squeeze in a fresh haircut. Efficient and stylish!

But the real highlight of day one? Dinner at Burger & Mayo. This place is a burger lover’s dream, and I went all out with their mac ‘n’ cheese burger. Yeah, it’s as ridiculous and amazing as it sounds. And Danielle—always keeping things interesting—ordered a cocktail that was smoked and served in an actual beaker. If that’s not some mad scientist drink vibes, I don’t know what is. Oh, and let me not forget to mention the cheese dip for the burgers. If you ever find yourself there, don’t skip it. Life-changing stuff.

Day Two: Wedding Day Fun and Surprise Rainstorms

The second day was all about the wedding. Destination weddings are always an adventure in themselves, and this one was no exception. We started the day with a good dose of caffeine at Kasalta, a nearby café and bakery. When I say their coffee was strong, I’m not kidding—it was practically rocket fuel, and it paired perfectly with their killer breakfast.

Once we were fully caffeinated and ready to go, we met up with Daniel to help capture the wedding day moments. Things were running smoothly, with the bride and groom getting ready, and the air filled with excitement—until the skies decided to open up. Out of nowhere, a massive downpour hit, and just like that, everything changed. Gotta love that unpredictable tropical weather!

But hey, rain or shine, the wedding must go on! The ceremony, originally planned for the outdoor courtyard at Casa de España, was quickly moved indoors. And honestly, it worked out perfectly. The vibe was intimate, and the couple did something I’d never seen before—they personally thanked every guest for being there at the end of their ceremony. It was a small, but seriously meaningful gesture that stuck with me.

The reception? Pure fun. The dance floor was packed, and everyone was living their best lives. I was happy to assist Darien with capturing the moments—documenting people letting loose, laughing, and celebrating made the entire day feel even more special.

Day Three: Exploring Old San Juan’s Colorful Streets

After the wedding craziness, we were ready for some casual exploration. Old San Juan was calling our names, so we grabbed an Uber and headed out to wander the historic streets. If you’ve never been, Old San Juan feels like stepping into a postcard—vibrant buildings, cobblestone streets, and history at every turn.

Our first stop was Bastion de las Ánimas, an old fortification dating back to the 1600s. I’m a sucker for history, so standing there, imagining the cannons protecting the bay, was surreal. But I’ll admit, my stomach was already thinking about lunch.

For that, we headed to La Garita, where I finally got to try mofongo. Darien and his wife had been talking this dish up for days, and it did not disappoint. Mofongo, if you’ve never had it, is like mashed plantains mixed with garlic, and it’s just perfect. We paired it with a few cocktails (because vacation mode), and after that meal, we were ready to walk it off.

We spent the rest of the afternoon documenting the charm of Old San Juan’s streets. There’s something so magical about the pastel-colored buildings that makes you want to stop at every corner for a photo. I even treated myself to a mocha latte at a cute little coffee bar tucked away in a courtyard—because why not? You can’t rush through Old San Juan; it’s the kind of place that invites you to slow down and just take it all in.

Evening: Rooftop Drinks and Live Music

After a full day of exploring, we decided to freshen up and prepare for a night out. Our first stop was the Catedral Rooftop Bar, which offered a casual, chill spot with great city views and even better drinks. I’ve been a fan of mezcal ever since Darien introduced me to it, so of course, I went for a smoky mezcal cocktail. It’s like tequila but with that rich, smoky flavor that makes every sip more interesting.

Later that night, we stumbled upon some live acoustic music at Catedral Basilica de San Juan Bautista. Picture it: acoustic tunes, a small crowd, and the kind of atmosphere that makes you want to sit back, sip a drink, and soak in the moment.

But the night didn’t end there. We ventured over to La Factoría, a bar known for its quirky, eclectic rooms. Each one has a different vibe, and in one, we found a dance floor with couples swaying to merengue. I couldn’t help but think, “One day, I’m going to learn how to dance like that.” But for now, I was content watching, mezcal in hand.

We closed out the night with a late-night snack from a nearby food truck before heading back to our Airbnb. Tired, but content, we knew we’d made the most of our San Juan adventure.

Final Thoughts: San Juan, You Were Perfect

This trip to San Juan was exactly what I needed—a mix of fun, spontaneity, and a little bit of work (thanks to Darien’s wedding videography). Whether it was indulging in a crazy mac ‘n’ cheese burger, getting caught in a rainstorm, or exploring the charming streets of Old San Juan, every moment felt memorable.

Puerto Rico, especially San Juan, is one of those places where you don’t have to break the bank or have a luxury experience to make the most of it. The food, the history, the local vibes—it all comes together to give you an unforgettable trip. If you’re thinking about visiting, do it. You’ll leave with a full heart, a full belly, and a camera roll that’ll make you smile every time you scroll through.

FAQs

Where is Calle Loíza?
Calle Loíza is a lively street in San Juan, known for its local shops, food trucks, and vibrant cultural atmosphere.

What is mofongo?
Mofongo is a traditional Puerto Rican dish made from mashed plantains mixed with garlic and often served with pork or seafood.

Is Old San Juan worth visiting?
Absolutely! Old San Juan is full of history, colorful architecture, and local charm, making it a must-see destination.

What makes mezcal different from tequila?
While both are made from agave, mezcal has a smokier, more complex flavor than tequila, thanks to its unique production process.

Where can I enjoy live music in San Juan?
You can catch live jazz or acoustic performances at spots like Catedral Basilica de San Juan Bautista, among other local venues.

What’s the best way to get around Old San Juan?
Walking is the best way to explore Old San Juan, as it allows you to take in the historic streets, beautiful architecture, and local cafes at your own pace.