Let's Take a Day Trip

SAN JUAN, Puerto Rico — This year, I made a promise to myself: explore more of the Caribbean. The places people romanticize. The places that look expensive from afar. The places that feel like a reward.

But I’m doing it intentionally — mindful of cost, peak seasons, and making sure the experience is worth every dollar. After watching Bad Bunny take over the Super Bowl stage, I booked a ticket to San Juan to see what the island really had to offer.

And it didn’t disappoint.

Before I even talk about the food, let me talk about the beach.

Located just minutes from Luis Muñoz Marín International Airport, Playa Isla Verde is one of the most accessible beaches in San Juan. The beach stretches wide and open, framed by tall palm trees that sway like they’ve been rehearsing for this role their entire lives. The sand is soft but compact enough to walk comfortably, and the Atlantic rolls in steady waves — not aggressive, but strong enough to remind you that you’re standing at the edge of something vast.

In the distance, high-rise hotels and condominiums line the shoreline, creating a modern skyline against the ocean. Families gather under covered pavilions. Music plays faintly from portable speakers. Kids run toward the water and back again. At one point, a plane descended overhead — a reminder that Luis Muñoz Marín International Airport isn’t far — and for a second, I just stood there watching it glide across the blue sky like a postcard moment.

It felt alive. Not secluded. Not overly commercial. Just balanced.

And then there was the food.

Friday evening, I headed to Distrito T-Mobile, where the entire complex glows as the sun sets. Pink and purple lights illuminate the structure against the darkening sky, palm trees silhouetted in front of it. The energy shifts as night falls — music drifting through the open-air walkways, laughter echoing between buildings.

I grabbed dinner at Arena Medalla, a sports-bar-style restaurant with an outdoor patio facing a stage that I imagine hosts live music on weekends. It felt relaxed. Comfortable. The kind of place where you settle in and let the night unfold.

I ordered bone-in barbecue wings, a well-done bacon cheeseburger, and curly fries.

The wings were smoky and sauced just enough to coat your fingers without drowning the flavor. The burger had that classic, satisfying bite — melted cheese blending into the beef, crispy bacon adding salt and crunch. The curly fries were golden and seasoned well, with that perfect crisp exterior that gives way to softness inside.

Nothing complicated. Just good.

The next morning was brunch, and in San Juan, brunch feels like an event.

We went to Christianson, known for its $35 endless mimosas. The atmosphere buzzed — glasses clinking, plates arriving at tables like trophies. No one looked rushed. Everyone looked like they were exactly where they were supposed to be.

I ordered the chicken and waffles with eggs and bacon. My cousin ordered “The Superstar” — eggs any style, French toast, ham, bacon, or sausage, plus tater tots and toast. She chose the strawberry cheesecake French toast.

When the food arrived, it filled the table.

The waffle had that subtle buttermilk flavor — fluffy inside, lightly crisp outside. The eggs were soft and buttery. The bacon crisped at the edges. I expected a traditional wing with the waffle, but I received a chicken tender instead. It was seasoned well and fried to a perfectly crisp finish.

The strawberry cheesecake French toast was the standout. Powdered sugar dusted the top. Butter melted slowly down the center. Strawberry drizzle adds layered sweetness without overpowering the dish. It wasn’t too much. It was just enough.

San Juan surprised me.

It gives you cobblestone streets in Old San Juan, colorful balconies with Puerto Rican flags hanging from them, modern skylines along the beach, and food that feels indulgent without being pretentious.

If I could do anything differently, I would carve out more time for deeper cultural exploration — maybe a guided tour, more local eateries tucked away from the main strips, or a sunset sail along the coast.

But as a first intentional dive into the Caribbean, this weekend delivered.

Come for the beaches.

Stay for the food.

And leave knowing you’ll be back.