Exploring Puerto Rico with my wife was unlike any trip we’d taken before. Just the two of us, from the cobblestone charm of Old San Juan to the misty heights of El Yunque, the island gave us history, nature, and a few surprises we definitely didn’t plan for (like hiking a mountain in flip-flops). We tried to soak in as much as we could—at our own pace—and ended up with the kind of moments you can’t really plan, but won’t forget either.

Old San Juan: Color, Culture, and Cobblestone

Wandering through Old San Juan feels like walking through a painting that’s been lived in for centuries. The pastel buildings, historic forts, and stone streets are beautiful in their own right, but it’s the energy that brings it all to life. It’s lively without being chaotic, and everywhere you turn, there’s something worth pausing for.

We visited Castillo San Felipe del Morro first, catching a stunning sunset from its outer walls. The breeze, the view, the light—it was one of those golden travel moments where everything just feels right. The next day, we explored Castillo San Cristóbal, which offered a quieter, equally impressive experience. Between the two, we took time to sit with the view, relax, and just let the place settle in.

Later that day, we walked near La Perla, slowly making our way back toward El Morro to catch another sunset. On the way, we stopped by La Puerta de San Juan—the iconic red gate that once served as the city’s main entrance—and hung around for a bit before making a quick visit to Save A Gato, a local rescue that helps care for the city’s cat population. The cats were unbothered, lounging in the sun, as if they owned the place.

We made time for local eats, too—mofongo and pasteles were standouts. No trip to San Juan would be complete without ending the night at a hidden gem, which for us, happened to be La Factoría. Hidden behind an unmarked door, this speakeasy-style bar is layered with moody rooms and killer cocktails. It felt like a secret that somehow everyone knows—and that’s part of the charm.

El Yunque: Hiking High, in the Wrong Shoes

El Yunque National Forest is like something out of a fantasy novel—thick rainforest, mist-covered peaks, and sounds that make you feel like you’re truly out in the wild. The original plan was a short hike to the Mt. Britton Lookout Tower. What happened instead? We kept going, all the way to the summit. And yes, I did the whole thing in flip-flops—mainly because I wasn’t planning on keeping my shoes on for long; I was hoping to jump into any watering hole along the way. Not my proudest gear choice, but it made for a great story—and a strong case for proper footwear.

We started early and had the trail mostly to ourselves. Reaching the summit was a workout, but the view made it worth every slippery step. At 3,540 feet up, the canopy opened to reveal endless green. The silence at the top, broken only by birds and wind, made it feel like we were somewhere sacred.

By the time we returned to the base, the crowds had arrived and the parking lot was overflowing. That contrast made one thing clear: go early. You’ll experience the rainforest in a completely different way.

Glow in the Dark: Kayaking a Bioluminescent Bay

Later that night, after returning to the hotel and getting much-needed rest, we headed out again—this time for a bioluminescent kayak tour through the mangroves. It was a no-moon night, which made the glowing effect even more vivid. Every paddle stroke lit up the water with tiny sparks of light, like underwater fireflies.

We didn’t bring phones—between the water and wanting to actually be in the moment, it felt better to just take it all in. And honestly, the photos wouldn’t have done it justice. It’s one of those experiences you just feel: peaceful, strange, beautiful. We floated through glowing tunnels, under the stars, completely in awe.

Túnel del Guajataca: Where History Meets the Coast

The following day, set aside for a driving day trip, we headed to Puerto Rico’s northwest coast near Quebradillas. There, we found Túnel del Guajataca, an old railroad tunnel that once carried sugar cane across the island. Today, it’s a short walk through the tunnel, which ends with a big reveal—cliffs, crashing waves, and a wild stretch of beach.

The tunnel itself is quick to pass through, but what’s on the other side lingers in your memory. Jagged coastline, strong surf, and signs warning visitors to stay out of the water set the tone: this beach is for looking, not swimming. Still, it’s a dramatic, beautiful stop, and walking through the tunnel feels like a scene out of a film—minus the danger (unless you count slippery rocks and rogue waves).

Cueva Ventana: Framing Nature

Cueva Ventana (“Window Cave”) lives up to its name. Perched on a cliff in Arecibo, the cave opens to a jaw-dropping view of the Río Grande de Arecibo valley. The hike in is short but rich in detail, especially if you go with a guide like we did—ours pointed out everything from petroglyphs to native bats to the way the cave shifts with time.

Standing at the edge of the cave’s “window,” with the valley spread out below, felt like stumbling across a secret lookout. It’s the kind of place that doesn’t just look good in photos—it actually feels good to be there. Quiet, surreal, and a little humbling.

What the Trip Taught Us

Puerto Rico doesn’t just hand over its beauty—you have to meet it halfway. Slow mornings, open afternoons, and a little flexibility went a long way. We didn’t try to see everything—just enough to fall in love with the place.

Some practical tips we picked up:

• Bring good shoes. You’ll thank yourself later.
• Go early—especially for hikes and popular spots.
• Don’t over-schedule. Wandering led to some of our favorite moments.
• Rent a car, but drive defensively—expect the unexpected on the road.
• Eat local. Mofongo, arroz con gandules, local seafood and pasteles are all musts.

We already started a list for next time: Cabo Rojo, Ponce, Aguadilla, maybe even a ferry ride to Vieques or Culebra. There’s still a lot left on the map.

Puerto Rico gave us history, nature, laughter, and more than a few stories. If you’re thinking about going—do it. And if you’ve already been—what did we miss?