Two Views of San Juan

Flying into San Juan meant landing in the unexplored. We hadn't yet visited this "isla de encanto" and weren't sure if the hurricane was still impacting daily tourism. What we found was a city rich with history, friendly residents, new food epiphanies (looking at you mofongo), and a new era of the city rising from last year's catastrophe.
Our trip played out in two stages - Old San Juan, complimented by the small luxury hotel, Hotel El Convento, a 17th century restored convent; and the beach-front Condado resort pennisula, where new & chic are the words of the day, and our boutique hotel, Serafina Beach Hotel (2023 update - this is now the Condado Ocean Club) opened just this year, leading a foray into Puerto Rico, post-Maria. Both were full of romanticism, although the mix was nostalgia with champagne. Without a passport.
Let's go back in time to start. Picture Havana in its glory, with crayon-colored houses and Caribbean breezes, without the revolution. Puerto Rico is Hunter S. Thompson's dream, full of rum and tropical heat, fancy cocktails and jibaro music. We found this come to life in bars, restaurants, street markets, and national landmarks across the city.
Street ambiance
When we took to the streets of old San Juan the color and salt-worn charm was captivating...we were ready for some rum punches and Puerto Rican cuisine.
El Jibarito was our first stop for libations and traditional wholesome nourishment. The rum punches were poured and we ordered some of the waitresses recommended dishes. Their pork ribs plate with plantain gravy was accompanied by rice and some of the most flavorful beans we've ever had. Simply delicious. One more round of rum punches and some extremely tasty fried cheese sticks (hard to go wrong there) and we were ready to continue exploring.
The presence of street art around old San Juan made many strong statements.
Food, OSJ:
Jibarito – Authentic, the aunt of the owner cooks everything, really great rum punches.
Princesa Gastrobar – Very yummy outdoor restaurant on this pretty strip outside the wall. Delicious drinks, live music, good seafood.
Verde Mesa – Upscale health spot, we basically just ate leaves & flowers, plus a duck dish that Jason loved, I left hungry and high as there was a lot of incense floating around. But super cute, really Soho’y.
La Bombanera – Cool old-school breakfast spot, opened in 1902. Fancy coffee maker, famous for this Puerto Rican sweet bread, Mallorcas, which are kind of like croissants, and are great for egg sandwiches.
Punto de Vista – You might classify this as a bar, but you’d be amiss to skip the Mofongo here. It’s a volcano of mushed plantains with creamy garlic shrimp exploding out the middle. I dream about it still. Also 2 for 1 mojitos.
Food, San Juan:
Santaella – DELICIOUS. We were only able to order three things per our lack of exercise and too small of stomachs, but literally everything on the menu looked good. Great cocktails too. Very chic, very nice, cocktails lighting on fire, that deal. Goat cheese quesadilla was amazing, ahi tuna pinxtos, also amazing, our entrée was a special of the day, some beautiful scallops over lentils with chorizo, mmm.
Acapulco – ALSO DELICIOUS. Low-key Mexican spot. Again, the problem with not being able to consume as much as we wanted. Great al pastor tacos & beans & guac. Spicy margs, always a plus.
Ceviche House – Peruvian food in a local spot. No frills, pretty decent ceviche.
1919 – We didn’t go but it seems really beautiful and upscale – tasting menu type deal.
Drinks:
La Factoria – Really awesome bar in OSJ. Multiple rooms, room 1 & 2 are open the whole time, room one is great for cocktails, room two is a wine bar, room three opens at 10pm and has dancing, room four opens… we don’t know when because we can’t last that long. This has the right vibes to make you feel like you’re in Havana before the revolution.
St. Germain – The house of an old revolutionary, now a bar (and restaurant but we didn’t eat here), with a really cool vibe, you can sit in the Juliet balconies overlooking the street, or on the rooftop… again, nice Caribbean breeze and vibes.
El Batey – Dive bar, with very interesting décor, a pool table, and a jukebox.
La Placita de Santurce – I cannot stress this enough, if you are there on a holiday or a weekend night, you must go. Local spot, many outdoor bars, outdoor music, everyone walking around with drinks, SO COOL.