Before I went to bed in my spacious room decked with coastal style at the Puerto Rico’s Aire de O:Live hotel (right down to a massive straw hat on the wall), I left the curtains open just a bit.
It’s not like anybody could peer in (though the only thing they’d see is me in my plaid pajamas).
The reason is, with the Aire’s location on Isla Verde beach in San Juan, I knew that once morning came the sun would be flowing in; a far cry from most of America cranking the heat inside and wearing hats and gloves when they venture out. I hope they don’t get too jealous of me.
Sure enough, on my first morning during my first visit to Puerto Rico I opened my eyes, looked out the window and saw the idyllic waves crashing onto the beach; symbolic since 2026 was about to crest into the calendar. What better place to ring in the new year than here, where a certain superstar has been happily exporting the island’s culture to the rest of the world; including his upcoming Super Bowl performance later this year.
But as the new year approached, I had a task at hand which was of the utmost importance: drink in the island: literally, figuratively, spiritually: you name it. After all, Puerto Rico is the land of rum (famously Bacardi, though Don Q seems to be a local favorite). As a result, it’s also the birthplace of the Pina Colada.
“Una cerveza, por favor”
Brushing aside any alcohol-soaked scandal, one of my first stops when I arrived at San Juan Airport was to take a 5 minute Uber to Bebo’s Barbequee; a local fixture which serves up homestyle comida like Pernil (slow-roasted pork), Mofongo (mashed plantains made here with plenty of garlic), which I all washed down with an ice cold Medalla beer, a beloved fixture of the island, handed to to me with an napkin wrapped around its neck.
After that luscious night at Aire de Olive, the first stop (after a perfect iced Americano on their roof) was the beach, where the hotel has a bevy of lounge chairs and umbrellas for guests. Naturally, I had to kick things off with its iconic Pina Colada: the ones here come from Kumo, one of the hotel’s restaurants, and I drank in the subtly sweet creaminess of the island’s trademark drink as I gazed out onto the water.
While the Pina was invented here, just don’t ask exactly where. There’s a boozey disagreement if it was at the Hilton Caribe or a regional favorite called Barrachina. For the record, the locals I spoke to seem to think the latter spot, which opened in 1949, is the rightful father of the cocktail.
Perfect Pisco
Aside from Kumo, the other restaurant at Aire de O:live is Awwa; their second-floor Peruvian Raw Bar. I’ve discovered that the food and drink of Peru is popular here. (I even later realized that a souvenir shot glass I purchased was made in Peru). Here at Awwa, I meet Executive Chef Marielys Hernández Nazario who noted their importance of using fresh seafood (today’ s catch was wahoo).
In fact, the word ‘fresh’ was top of mind with every bite, from an Oyster platter (so fresh), a colorful ceviche made with Canchitas and Camote (fresher than fresh) and the deconstructed crab cake that is Crab Causa (fresh x3). And it wouldn’t be a Peruvian spot without a Pisco Sour; theirs is a clarified version made with Gooseberry & Thyme Foam.
New Year’s Eve-spresso Martinis
To say adios to 2025, it was time to decamp to Condado; a bustling beachside urban area packed with restaurants, bars, and hotels. The AC Hotel San Juan Condado is situated squarely in the middle of the action. Its rooftop boasts a pool with citywide and beach views, along with Bar.C.lona, a rooftop that slings local dishes for lunch and dinner. It also hosts events, like a ticketed new years party for tonight.
When it came time to countdown to midnight, I glugged back an expertly made espresso martini made with Alto Grande; a popular coffee brand in these parts; its navy and white logo is plastered everywhere. (During my visit, I also tried Cafe Lareno, another delicious local coffee.) It should be noted that the AC Hotels (not just here in warm San Juan) boast ACGT’s: that’s A Custom Gin and Tonic to the layman. I’m told it’s served in a scientifically-engineered glass with the perfect blend of ingredients. How do they know it’s perfect? Well, it’s science! Naturally because the AC Hotels originated in Spain, they also have perfected the art of Tapas.
When it came time for fireworks, I headed to my room’s balcony (pro tip: ask for one when you check in) and I gazed at a bevy of them blasting off and sparkling up San Juan night sky.
A Champagne Cheers
As 2026 dawned, I went from my room at the AC up to their rooftop pool and enjoyed some of that Puerto Rican sun while splayed out on a lounge chair.
I was blissfully hangover-free and ready for a nearby massage I booked through Resort Pass, which allows you to enjoy the amenities at resorts and spas without actually staying there. From the AC’s central location, for a change of scenery I made my way to Elemara Spa & Salon at La Concha Resort where I was handed a glass of champagne (which comes with the spa package) and had an hour-long treatment. If there’s a better way to ring in a new year, I don’t know of one.
By evening, it was time to again depart the AC and explore historic and colorful Old San Juan which is teeming with tourists exploring its majestic castles, sweeping green fields full of kite-flyers, and spectacular seaside sunsets.
Even more stupendous? A short walk away is La Factoria; one of the island’s most-lauded watering holes (it’s a member of the World’s 50 Best Bars) and is fully ingrained in local culture. How ingrained? Well, it was featured in the music video for the Luis Fonsi smash “Despacito,” for one! I managed to grab a seat at one of their eight bars that make up the complex and ordered a fruity Champeta (Don Q rum, ginger and a pineapple fermentation).
A Vodka Tonic for New Year’s Day
As the sun set on New Year’s Day it was time for dinner at Caña, one of the many restaurants at the acclaimed Fairmont San Juan with a menu overseen by Chef José Enrique, who was the first local Puerto Rican to be recognized by the James Beard Awards. A stately property with a casino, the Fairmont itself is the kind of place with massive chandeliers hanging over slot machines, huge carpeted staircases and live local music in a bustling lobby.
Caña is uniquely Puerto Rican and it turned out to be a greatest hits rundown of what I’ve eaten and discovered on my trip: the mofongo was served in a heaping pile, while a lobster soup (Asopao De Langosta) was filled with spices was as extravagant and satisfying as it sounds.
Not taking itself too seriously, I ordered a side of rice and beans (served separately), along with another deconstructed crab cake (Blue Crab, alcapurria, pique criollo emulsion). I washed it all down with a Ketel One Vodka tonic, with a sprinkle of fresh lime. There’s that word again. Cocktail standouts at Cana include a Guava Island Mojito (light rum, dark rum, guava syrup, fresh pineapple juice, fresh lime juice, mint).
I’m inspired and refreshed by the people, places and drinks that make up Puerto Rico. And if there was ever a story of resilience, it’s here. Walking around, it’s hard to believe they experienced the crippling effects of Hurricane Maria not too long ago, which destroyed so much here; crippling the power supply and sadly killing nearly 3,000 people.
Today, it’s an island back in the global spotlight but for all of the right reasons. For that, I raise my glass to cheers its comeback.
Another Pina Colada, por favor.
Trip guide:
Aire de Olive Hotel
AC Hotel Condado
Awwa Raw Bar
Cana
Bebo’s Barbeque
La Factoria
Hilton Caribe
