Traveling for work is awesome. Someone else pays for us to go to faraway places and shoot pretty things. We can’t complain! But one drawback is that traveling for work has made us hate the airport. Southwest’s ‘no seat assignment’ policy and all the germy people that will potentially enter our personal ‘no fly zones’ before we reach our destination turns us into evil trolls, forcing us to make the next experience as short and painless as possible. So this past June when we found ourselves searching for an adventure-style getaway without the hassle of 1) customs and 2) another long ass flight, the only place that made absolute sense to us was of course, San Juan. For those of you who poo-poo the idea of Puerto Rico being a real adventure, I’m just gonna say: you are wrong.  We spent seven delightful days in a sweet AirBnb, wandering up and down old streets, drinking Haitian voodoo rum, basking on empty beaches, eating (and sweating) our way through.

Although, we probably wouldn’t do it the same way again or stay as long—the next time we’ve got four days to get (quickly) outta dodge, this is what we’d definitely do again:

Get lost on the streets of Old San Juan at sunset. There’s a magic to the light that streams through the alleys and streets of OSJ. Near dusk, prepare to blows up the instagram with your sick ‘Sunset in San Juan’ pics. and No! The street’s not wet, the blue bricks have developed this natural shiny patina from centuries of wear. It will be more than you can stand. Definitely walk the Paseo de la Princesa and around the city wall or ‘La Muralla’. Gorgeous.


Rent an Airbnb with a balcony.  At around 4pm, sit on balcony and drink rum. Drink only Ron Del Barralito rum. Don’t ask for Bacardi. Don’t ask for Captain Morgan. Trust me, you will be treated differently if you ask for Ron Del Barralito. Act like you know.

This was not our balcony, but it's nice, right?
This was not our balcony, but it’s nice, right?

Go to Calle de San Sebastián to experience the coolest bars for the non-touristy set. We loved Bodega Chic for its low key vibe and busted out decor, Taberna Lupulo for little bar snacks and impressive rum collection, El Batey was a novelty must-go in terms of the epic graffiti walls and OSJ dive-bar lore, but that’s kinda where the love ends. La Factoria answered a lot of bar/food/cool vibe needs in one fell swoop. & bonus–it’s a bar behind a bar behind a bar behind a bar. Not kidding. You walk in (there’s no sign outside) and it’s this great authentic OSJ dive bar, complete with high ceilings, crumbling walls, old furniture and mood lighting. The two saloon style doors that don’t look like they will lead you anywhere take you to another bar–this one is a cozy narrow space that feels like a chic wine bar. The next set of doors takes you to a dining room with amazing giant paintings on the walls and a delicious menu if you want more than bar nibbles in Bars 1 & 2. The very back bar (which is not pictured here) is a giant space with bar and dance floor. This spot really felt like where locals come to dance, latino style—in other words, you better know how.

Go to Hosteria Del Mar Hotel in Ocean Park. Strolling at sunset happens for a reason. It’s pretty damn hot during the day. Some like to go to the forts, but we liked to go the beach. (The time we decided we needed to see at least one fort while in OSJ had us sweating and walking way more than we liked, so we only did that once. And we were fine with that.) Our absolute favorite beach was in Ocean Park at the Hosteria Del Mar hotel. This was like the most perfectly perfect bohemian spot tucked somewhere in between the high rises and local homes. It’s worth the daily trek from OSJ, but next time I’d stay 1 night in OSJ and two or three nights here. To get there from OSJ, you can walk (it’s kinda far) or take a bus (if you like waiting for long stretches of time in the heat) or indulge and take a cab. We walked the first few days to different beaches nearby–the furthest being Condado, but when we found Ocean Park, we splurged on the cab rides out there. Worth every penny.

Take in all the visual delights of OSJ. Everywhere you look is mind blowing. Everything. The streets, the graffiti, the architecture, the palm trees, the beaches, the walls, the windows. It’s just beautiful. You gotta walk it out to find it though, and just keep on walking, relishing in the pending score of your short flight home with no change in time zone and no customs…