The moment you step foot inside the vast lobby at Caribe Hilton, you can feel the history of this property all around you. It’s like an instant vibe check, as if you’ve been transported back in time without losing any of the joys and perks of modern amenities. And a lot of it has to do with an alluring mural past the front desk area and just beyond the entrance to Ruth’s Chris Steakhouse.
In fact, a guest might entirely miss it because of the view through the massive glass wall beyond the Caribar. This is the spot, after all, where bartender Ramón “Monchito” Marrero mixed rum, coconut cream, and pineapple juice for the first time and became the inventor of the piña colada. Thus, the mural celebrates the man, myth, and legend and role he and a simple cocktail played in creating a lasting legacy for this popular resort.
But the history of this bar and building will only captivate a guest for so long before today’s creative mixologists steal the spotlight. I must have spent several hours on my stool, gleefully watching as one bartender after another stepped forward to make me phenomenal signature cocktails that I assume would have made Monchito proud—and probably a little jealous. If I was awarding a trophy that evening, it would probably go to the Rum Fashioned that stole my heart, and it’s becoming an increasingly common drink, sure, but these guys had twists and special tricks for days.
Caribe Hilton earned legendary status for its history, but its modern improvements and additions have made it the kind of property a family can visit and rarely leave. Multiple dining options will please even the pickiest eaters, and I’d be lying if I said I didn’t visit Mojito’s Caribbean Fusion twice during my visit so I could proudly declare that I drank not only the Super Margarita but the Colossal Margarita as well.
Still, I had to get out and explore, because if there’s one thing Puerto Ricans are extremely proud of, it’s their food. Everyone had a recommendation for places to eat in San Juan and a little beyond, so I made notes, stretched my legs (or wiggled my Uber thumbs), and set out to find some of the best.
Marmalade
When I asked staff members at Caribe Hilton for their top pick for a restaurant they’d choose for a night out, Marmalade was the runaway winner. It is easily one of the most creative dining options in Old San Juan, as Chef/Owner Peter Schintler’s concept only offers tasting menus, so guests should keep an open mind and know they’re about to have an eclectic affair. From appetizers like organic beef tartar and “sushi esque” paella to exceptional entrees like wild Mediterranean turbot and natural, hormone-free lamb tagine, no one will be disappointed.
More than anything, this is probably the best choice for larger groups because while five or less people will enjoy five courses, six or more will have the immense pleasure of tasting 14 courses. That’s a lot of photos to take for any Instagram account, but the experience is beyond amazing.
El Jibarito
Now, when I asked for authentic local cuisine, quite a few fingers pointed in the direction of Old San Juan, where El Jibarito has some of the most in-demand tables in town. In fact, because you can’t make reservations and the wait can be as long as an hour depending on the time of day, I was encouraged to eat here by myself, as parties of one tend to get in and out much quicker than groups.
Lote 23
In terms of finding the ideal mix of authenticity and variety, there’s little wonder why the “gastronomical park” Lote 23 quickly ascended to one of the most exciting settings on the entire island. From Budare’s arepas and El Cuchifrito’s mofongo to mouth-watering mac and cheese and amazing burgers, even the pickiest eaters will become wannabe food influencers here.
And no one should leave without grabbing one of the creative cocktails from Caneca, where brilliant mixologists Leslie Cofresí and Roberto Berdecía blend fresh juices and generous pours from the coolest Airstream trailer setup.
Santaella
Upon first glance, the menu for Chef José Santaella’s signature restaurant seems like a dream. For appetizers alone, guests won’t want to be pinched as they choose from the extensive list, and decisions won’t be much easier when it comes to seafood and meat choices. But that’s a fantastic problem to have in a destination known for spectacular food, and this charming spot has quickly become a favorite for locals and tourists alike.
Located in La Placita Marketplace, Santaella is also a dynamic choice for special group events, so be it a destination wedding or milestone anniversary, families and friends can gather with the confidence that they’re about to have a truly memorable meal.
1919 Restaurant
One of the things I love about visiting Puerto Rico resorts is how the island’s sense of national pride and camaraderie doesn’t restrict people from one property recommending dining options at other places. In fact, many of them will insist that you get out and explore, and that’s typically when they’ll lean in and whisper their best recommendations. At least that’s how I was encouraged to give the 1919 Restaurant a go.
Located at the Condado Vanderbilt Hotel, this world-famous establishment is run by Michelin Star-rated Executive Chef Juan José Cuevas, whose “flavor-forward” philosophy guarantees a phenomenal meal. But one of the dining concepts at the top of my Caribbean bucket list is the 1919 Cellar Experience, which is a private, bespoke event for just four guests, and features a wine and cheese pairing from the sommelier. Follow that up with the cigar and whiskey option and you’ll probably feel like the most important person on the island.
Señor Paleta
The popsicles at Señor Paleta are already the stuff of legend, so when someone recommended stopping at the brick-and-mortar location in Old San Juan, I was already halfway out the door. That spot is one of those places that everyone should visit during a Puerto Rican vacation, just because you need a selfie to prove you were there. Otherwise, there’s also a kiosk at Lote 23, which just reaffirms that it is a complete dining experience for everyone.
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Sure, this one will likely raise an eyebrow or two since massive commercial plazas don’t exactly scream culinary authenticity, but there are some phenomenal dining options here. For starters, La Central by Mario Pagán is as stylish a setting as its menu is creative. I stopped here just for the Ron y Tabaco cocktail, but the way people talked about the swordfish, dinner also became the priority. What really blew me away is how every dish includes sugarcane or rum, proving as always that the smallest touches can go a long, long way.
That wasn’t my only meal in the plaza. More people recommended Sazón Cocina Criolla than any other restaurant, so even though it meant taking the one available chair between complete strangers, I had to find out if the hype delivers. Especially since mofongo is always on my list, so I doubled up here with the octopus and skirt steak versions, and, quite frankly, I haven’t stopped thinking about both dishes.
