Jessamy & Josh
Things To Do
Castillo San Felipe del Morro San Juan
Take some time to explore the 16th-century citadel that's also an UNESCO World Heritage Site
Catedral de San Juan Bautista
This is the oldest cathedral in the US - dating back to 1521! The inside is beautiful and worth peeking in for.
Paseo de la Princesa
This promenade dates back to 1853 and you'll be able to see the walls that once served to protect San Juan. There are gorgeous views of the San Juan Bay, and at the end of the walk, you’ll enter through the San Juan Gate into the heart of the Old City just as travelers did centuries ago.
Carlis Fine Bistro
The Beach Boys' pianist owns this place, which is home to an award-winning bartender who is as friendly as he is talented. We recommend the Maverick cocktail.
El Jibarito
Great place for genuine Puerto Rican food
La Taberna Lúpulo
Craft beer hall with the best selection in the Caribbean
La Factoría
You may recognize this place from the Despacito music video. Recently named one of the top 50 bars in the world!
La Cubanita
This is the sister bar to La Factoria and is much more low-key. Try the hibiscus cocktail that is made with the local Ron del Barrilito rum!
Chocobar Cortés
Satisfy your sweet tooth here - they also have a fantastic brunch menu!
Il Bacaro Venezia
Don't let the limited menu fool you - this place has fantastic Italian pastas! A heads up though that there is limited seating.
The Mezzanine
The three-level cocktail bar has historical significance (look for bullet holes behind the second-floor bar). If you want wine and tapas, head to the third floor!
Señor Paleta
They have a wide selection of popsicle flavors, so it'll be hard to go wrong. Beware of the long lines that may remind you of YoPo (looking at you Chapel Hill folks).
Playa Papaya
If you're craving something healthy, this place has great salads and acai bowls
Pera Maraya
Funky menu with delicious food and great cocktails. If they have the salmon & gnocchi dish, it's a must try!
Casa Bacardí
Book a distillery tour and learn about Puerto Rico's long history of rum!
Serafina
Italian restaurant in Condado that also has great cocktails!
El Yunque
Rainforest not too far outside of San Juan that has hiking and waterfalls
Additional Inspiration
From Conde Nast Traveler - March 2021