San Juan


When 15-degree days were the norm this past winter, Erin and I scoured the internet for a flight to somewhere, anywhere, that was warm. Our Golden Ticket out of the polar vortex came in the form of an under-$300-airfare to the sun-soaked paradise of San Juan, Puerto Rico. Just about a four-hour flight from JFK, San Juan was the perfect vitamin D laced remedy for our Seasonal Affective Disorders. 


Stepping off the plane and into San Juan's shroud of heat and humidity is met with the sensation of pure glee. Once you get to your apartment or hotel, popping open a can of a Medalla, Puerto Rico's ubiquitous beer, should become your top priority.  Make sure you stay in a spot that has beach access as to not waste anytime. Condado is a a popular area to stay and offers a great mix of hotels, condos, and restaurants right on the water. 

The island of Puerto Rico is relatively small, so if you're staying for longer than a few days you can cover a lot of ground. The majority of your days in San Juan should be spent lounging around with a pina colada in hand, admiring your fresh tan lines. However, spending some time checking out these nearby areas will delight your more adventurous side:

  • El Yunque Rainforest: buy tickets for a tour (which includes the 40-minute ride out of San Juan in advance).
  • Playa de Luquillo: for an authentic Puerto Rican beach hopping experience. Be sure to stop by the area's bodegas to grab a fresh coconut with rum and some pastelillos (delicious deep-friend meat patties). Plan on renting a car in order to get here..or meet a local named Jesus who will drive you there, as we decided to do.
  • Old San Juan (aka Viejo San Juan): for its nightlife. It's the perfect place to mingle with San Juan's unbelievably friendly and lovable locals.  El Batey, La Factoria, and La Taberna Lupolo are all incredibly fun spots.


From Luquillo's bareboned-yet-lively beach bodegas to the sit-down spots of Old San Juan, Puerto Rico's restaurants are well-loved extensions of the area's vibrant, Caribbean culture. Immerse yourself in every meal and savor the tropical, open-air atmosphere.

  • The Parrot Club: for some ceviche in Old San Juan.
  • El Jibarito: a more low-key resto that's great for dinner before a night out in Old San Juan. 
  • Caficultura: for a breakfast of champions consisting of banana rum pancakes.
  • St Germain: for lunch or brunch before a day exploring Old San Juan. 
  • La Casita Blanca: homey Puerto Rican food in Santurce (Condado). 

And make sure you try some mofongo, a classic Puerto Rican dish that consists of fried, mashed plantains.


Listen to lots of Hector Lavoe before you go. The Puerto Rican musician is known for originating the even sexier, more aggressive sounding salsa made popular during the late 1960s and 70s. 


Have a reliable recommendation or sweet spot to share? Go crazy in the comments section.