Puerto Rico

Day 1: Escaping a bomb cyclone, mofongo, and a reggaeton music video

We still can’t quite believe we made it. A massive “bomb cyclone” swept across the US on the night of our departure, canceling 64% of flights from Seattle and delaying another 30%. Our flight was one of the lucky 6% that departed on time. We slid down our icy hill in a Lyft, crawled past a multi-car accident on the airport access road, and sprinted to the gate with five minutes to spare. Shortly after takeoff, neighbors sent us videos of police cars crashing on our street and parked cars sliding into each other like an automotive conga line. We felt extremely, profoundly grateful to be on that plane — and also slightly guilty about our good fortune.

We landed in San Juan just as the sun was setting over the Caribbean in impossible shades of orange and pink. A giant billboard featuring Daddy Yankee and Jennifer Lopez confirmed we had definitely arrived in Puerto Rico. When we stepped outside, it was 79°F (26°C) — roughly 50 degrees warmer than what we’d left behind. Despite not having slept in 38 hours and running on nothing but adrenaline and airport coffee, we felt surprisingly energized. The warm Caribbean air will do that.

As soon as we checked into our hotel in the lively Santurce neighborhood, we made an impulsive decision: despite our exhaustion, we walked over to Calle Loíza — the place to be on a Friday night for locals who actually know where to go. We headed straight to Ana’s Café for our first taste of traditional Puerto Rican food: mofongo (mashed plantains, much better than it sounds) topped with shrimp in criollo sauce, empanadillas de queso, and tres leches for dessert. Everything was fantastic.

We walked around the neighborhood for a bit to soak in the electric evening atmosphere and work off some of our meal. Puerto Ricans really do know how to party, and they’re not subtle about it! Reggaeton music absolutely blasted from multiple clubs, competing for attention. Beautiful women dressed to impress passed by in groups. Men paraded their flashy cars and thunderously loud motorcycles up and down the street in an impressive display of “look at me” energy. It felt like we’d been inserted directly into the middle of a reggaeton music video, complete with the soundtrack and the aesthetic.

Eventually, exhaustion caught up with our adrenaline, and it was time to return to the hotel and sleep. We’d been awake for far too long, and even Caribbean energy has its limits.

• Hotel: Dream Inn
• Dinner: Ana’s cafe

Day 2: Pastries, tiny planes, and glowing water

Breakfast at Kasalta bakery was memorable — pan de Mallorca (spiral sweet bread with powdered sugar) and pastelitos de bacalao (crispy salted cod croquettes). Both so good we immediately started planning a return visit.

We took a tiny plane to Vieques, with Bea riding shotgun next to the pilot, which she absolutely loves. Vieques is a small, wonderfully laid-back island off the east coast of Puerto Rico, where the pace of life moves at roughly half the speed of the mainland and “hurry” is not in the local vocabulary. We checked into Malecón House, a charming boutique hotel right on the water, then headed to the Rompe Dieta Lula food truck — the name translates to “diet breaker,” which tells you everything about their philosophy. We tried an assortment of pastelillos, alcapurrias, and papas rellenas — all variations on the theme of “delicious fried things with tasty stuff inside” — and spent the afternoon on the beach watching the sunset.

Later that evening, having somehow found room for more adventure, we took a kayak tour to witness the bioluminescence in nearby Mosquito Bay. We’d taken a similar tour in the Cayman Islands a few years ago and really enjoyed it, but the experience here in Vieques was dramatically better, with a much higher concentration of the particular dinoflagellate plankton that causes this magical effect. Trillions upon trillions of these microscopic organisms reside in this bay, spending their days absorbing nutrients and sunlight like tiny solar panels, so that at night they can emit a brilliant blue flash of light whenever they’re disturbed. It’s essentially a chemical defense mechanism, but the result is pure magic.

The effect is genuinely spectacular when kayaking across the bay on a moonless night. Each stroke of the paddle creates an explosion of swirling, shimmering blue light that looks almost artificial in its intensity. We were paddling in a transparent plastic kayak, so whenever we looked down through the clear hull, we could see thousands of tiny blue sparkles zipping past beneath us as we glided across the dark water, like we were flying through a starfield. We could see our own hands and arms glowing and shimmering after dipping them in the water, covered in luminescent plankton. Fish swimming past left comet-like trails of blue light. It was surreal, beautiful, and quite magical — it was like we accidentally stumbled into a fantasy novel.

• Breakfast: Kasalta
• Lunch: Rompe Dieta Lula
• Taxi service: Marta +1 410 733 0393
• Bio bay tour: Taino Aqua Adventures
• Hotel: Malecón House

Day 3: Triple-islanding (a new personal record)

After a lazy morning that involved sleeping in, lounging by the pool, and generally doing as little as possible, we had an excellent brunch that fortified us for adventure. Then we accomplished something we’d never done before: we triple-islanded. Having flown to Puerto Rico on a commercial jet, then to the smaller island of Vieques on a tiny propeller plane, today we waded through knee-deep warm water across a submerged sandbar to reach the even tinier island of Cayo de Tierra, off the south coast of Vieques.

We found ourselves pondering important questions: Can this recursion continue indefinitely, like the Mandelbrot set? How much smaller can the islands possibly get? Is there a micro-island off the coast of Cayo de Tierra that we could swim to? At what point does it stop being an island and just become a large rock? We didn’t find definitive answers, but we enjoyed the philosophical speculation.

It was genuinely fun to explore the Cayo, which is small enough that you can walk around the entire thing in maybe 20 minutes if you’re moving with purpose. More importantly, we were delighted to discover a beautiful and wonderfully secluded two-person beach waiting for us — the kind of spot that looks photoshopped but is completely real. We had it entirely to ourselves, which felt like winning a very specific lottery. We relaxed in the shade, we swam in the impossibly clear ocean, and after a while we spotted a sea turtle swimming gracefully nearby, completely unbothered by our presence and living its best island life. What a genuinely pleasant way to spend a Christmas afternoon!

By the time we waded back across the sandbar to Vieques — carefully timing our crossing to avoid the deeper water at high tide — the sun was setting and painting the sky in dramatic colors. As we walked back along the beach to our hotel, we encountered wild horses frolicking in the surf, because apparently everything in Vieques is slightly more magical than elsewhere. A fun Christmas for everyone, humans and horses alike!

• Brunch: Tradewinds cafe

Day 4: The pursuit of fried plantains

We’re making excellent progress on our ambitious list of Puerto Rican foods to try, though our waistbands may have a different opinion about this achievement. Among other delicious things, today we had the local version of rice and beans (a Caribbean staple that somehow tastes different in every single country), as well as amarillos (fried sweet plantains that achieve that perfect balance of caramelized on the outside and soft on the inside). We loved the fried plantains so much that we’ve now made it our mission to learn how to make them at home, though we suspect they’ll never taste quite as good without the Caribbean atmosphere.

After a leisurely morning and an excellent lunch that may have involved more plantains, we decided to explore more of Vieques’ beaches. We walked to the end of Esperanza beach — the town beach where we’ve been based — and then continued along the full length of Sun Bay beach, which stretches on for what felt like miles. There were plenty of locals and tourists enjoying the sun, sand, and gentle waves, some with elaborate beach setups involving umbrellas, coolers, and portable speakers. But with around 2 miles (3+ km) of pristine shoreline to work with, it was remarkably easy for us to find a secluded spot of our own, perfectly sheltered by swaying coconut palm trees.

The breeze was absolutely perfect — just strong enough to keep things cool without blowing sand everywhere — and the sound of the waves breaking rhythmically on the shore was so deeply soothing that we almost fell asleep right there in the sand. We managed to stay awake, but only barely, and only because we didn’t want to get sunburned while unconscious. We stuck around until well after sunset, watching the sky turn from blue to orange to deep purple, then walked back along the now-darkened beach by the soft light of the new moon. There’s something deeply romantic about walking on a Caribbean beach at night, with just enough moonlight to see where you’re going but not so much that it ruins the stars overhead.

• Lunch: Bananas

Day 5: Potholes, wild horses, and beaches worth the detour

Having already thoroughly explored the beaches within walking distance of our hotel, today we rented a scooter so we could venture further afield and see what else Vieques has to offer. Fortunately, the rental company provided us with a scooter equipped with sturdy knobby tires, because the roads on Vieques are…well, let’s charitably say they’re “not exactly perfect.” That’s putting it mildly.

In fact, we rode on considerably more dirt, gravel, and loose sand than actual pavement, and even when we did find pavement, it was generously decorated with potholes of impressive size and depth. Add to that the various obstacles casually left behind by the numerous wild horses who roam freely and apparently don’t understand traffic etiquette, and you’ve got yourself an adventure. We never felt genuinely unsafe because everyone drives slowly here — it’s less a choice and more a necessity given the road conditions — but we were definitely glad to have some off-road motorcycling experience from our past adventures. Although the rental scooter certainly doesn’t compare to our adventure motorcycle back home in terms of power or capability, it handled the challenging terrain just fine and only complained a little bit.

After exploring some of the more questionable backroads and successfully avoiding most of the larger potholes, we stopped at Caracas Beach on the north side of the island. The water there looked so impossibly inviting — that perfect shade of turquoise that doesn’t quite look real — that we immediately parked the scooter and went for a swim. We floated in the gentle waves for a long time, probably longer than was strictly necessary, just enjoying the warmth and the lack of any agenda.

After eventually drying out in the sun and reluctantly accepting that we should probably see other beaches, we climbed back on the scooter and rode further down the coast. We ended up at La Chiva Beach (also known as Blue Beach), a long, sweeping stretch of white sand with occasional palm trees and very few people. The beach was extremely inviting, and we couldn’t resist a relaxing barefoot walk along the water’s edge.

We rode around a bit more, exploring dirt roads that may or may not have been actual roads, making absolutely sure we returned before dark because navigating potholes by scooter headlight didn’t sound appealing. All told, it was a very fun day with just the right amount of adventure and relaxation! We’re starting to understand why people fall in love with Vieques and never quite manage to leave.

• Scooter rental: Fun Brothers

Day 6: Puff pastry enlightenment (and urban art)

This morning we boarded a small plane — which is starting to feel like our preferred method of travel, honestly — and returned to San Juan, where we’re staying once again in the Santurce neighborhood. Our first priorities upon arrival were obviously food-related. After a tasty lunch at La Coffeetera, a trendy spot that perfectly captures Santurce’s hip vibe, we made the critical pilgrimage to Kasalta for dessert.

This is where we had a life-changing experience. We’re not being dramatic — well, maybe a little dramatic. At Kasalta we sampled another Puerto Rican specialty that was prominently featured on our must-try list: a quesito. How to describe this marvel of culinary engineering? Imagine the filling of cheesecake, whipped into a light and airy consistency that somehow feels both indulgent and delicate, all wrapped lovingly in flaky puff pastry and baked to golden perfection. It’s absolutely heavenly! We may have made audible sounds of appreciation. We’re not proud of it, but we’re also not apologizing.

With our blood sugar appropriately elevated, we spent the afternoon exploring the neighborhood on foot. This part of Santurce is genuinely full of fascinating contrasts — it simultaneously manages to be gritty and dilapidated while also being artsy, trendy, and genuinely happening. It’s a neighborhood that hasn’t quite decided what it wants to be when it grows up, and we mean that as a compliment. We spotted fashionable boutique clothing stores next to abandoned buildings, cute international restaurants with sleek modern decor sharing walls with decades-old shops, and — our favorite discovery — a completely free used book exchange made of milk crate shelves lining an entire outdoor wall. Take a book, leave a book, no questions asked.

Creative murals of all styles and influences adorn the sides of several old buildings, turning the neighborhood into an open-air gallery. Some are political, some are purely aesthetic, some we didn’t quite understand but appreciated anyway. There’s a constant stream of fashion-forward people coming and going, dressed like they’re either heading to or coming from somewhere much cooler than wherever we’re going. We’re having an absolute blast exploring Puerto Rican culture here — it feels authentic and unpretentious in a way that’s increasingly rare in popular tourist destinations.

• Lunch: La Coffeetera
• Dessert: Kasalta

Day 7: Pristine streets, professional photos, and an unexpected invitation

Old San Juan is the polished opposite of gritty Santurce — pristine colonial architecture, immaculate streets, and houses painted in pastel colors that would look ridiculous anywhere else but work perfectly here. Every building looks freshly painted, and the whole place has the quality of a movie set. We arrived early to meet Raúl, a talented local photographer we connected with through Airbnb, who showed us the old town’s most photogenic spots while simultaneously taking professional photos of the two of us. He had an eye for composition, infinite patience with our awkward posing, and a genuine love for his city. We came away with photos that actually make us look like we know what we’re doing.

We spent the rest of the morning walking through the old town — past imposing colonial-era forts that have withstood centuries of attacks and hurricanes, along streets lined with colorful houses, and through beautifully maintained gardens with ocean breezes and views of the Atlantic crashing against ancient walls. It’s Instagram-ready at every turn, and we took full advantage.

Later in the afternoon, we ventured to La Perla — the neighborhood made famous by the Despacito music video. We’d heard a tourist recently got into trouble there, so we did what we always do in these situations: put the camera away, befriended a local, and asked what’s actually safe. Bea used her best Portuñol — that delightful hybrid of Portuguese and Spanish that somehow gets the job done — to start a conversation with Carlos, who was sitting outside his house, guarded by a full-sized mannequin in a Star Wars stormtrooper helmet. Carlos turned out to be incredibly welcoming. He explained which alleys are picturesque and which ones to definitively avoid, and when he saw us eyeing his eccentric decor, he invited us inside.

His house was compact in the extreme: a bed, a motorcycle (yes, inside the house), a complete drum kit, three guitars on the walls, and Christmas lights draped across the ceiling. “I really need to get some proper guitar lessons,” he told us humbly, despite the clear evidence that he was already musically talented. True Puerto Rican hospitality from a complete stranger who couldn’t have been more warm and welcoming — we’re still smiling about it.

• Airbnb experience: Photography tour with Raúl
• Breakfast: Cafetería Mallorca
• Lunch: Cayo Caribe
• Dessert: Chocobar Cortés

Day 8: The art of doing nothing (Puerto Rican edition)

Today was intentionally a chill day — we’ve been going pretty hard with all the exploring and adventures, so we decided to dedicate today to the noble pursuits of sampling more food and relaxing at our local beach. Our hotel is situated in what we’ve come to realize is an extremely convenient location, positioned almost perfectly halfway between the hip, happening Calle Loíza (with its endless restaurant options and nightlife energy) and the upscale Ocean Shores beach (with its expensive houses and wealthy residents). We spent the day experiencing the best of both worlds, which felt like a well-deserved vacation from our vacation.

We’d already roamed Calle Loíza and the surrounding streets quite a bit over the past few days, but somehow the more we explored, the more we kept discovering restaurants we desperately wanted to try. It’s a delicious problem to have, honestly. Today we went to Pinky’s for a fantastic brunch. Later, we went to Qué Chido for legitimately great tacos that would hold their own anywhere in Mexico. We’ve been genuinely and consistently impressed with the food here in Puerto Rico! It doesn’t seem to matter whether we order traditional Puerto Rican dishes, American comfort food, or international cuisine — the quality has been impressively high across the board. Either we’ve gotten incredibly lucky with our restaurant choices, or Puerto Rico just takes its food very seriously. We’re betting on the latter.

In the afternoon, feeling appropriately full and slightly lazy, we wandered around the conspicuously gated neighborhood of Ocean Shores and along the adjacent beach. We entertained ourselves by picking our hypothetical favorite among the expensive houses, strolled along the beach at sunset watching the light paint the sky in increasingly dramatic colors, and indulged in some pleasant daydreaming about what it would actually be like to retire in Puerto Rico. The warm weather, the incredible food, the friendly people, the beaches — we could definitely see ourselves getting used to this lifestyle.

• Brunch: Pinky’s
• Dinner: Qué Chido