• brandenfugate

Rotten City Guide: San Juan

Updated: Apr 10, 2019

There's never been a better time to visit Puerto Rico and a trip there wouldn't be complete without spending a little time in San Juan. It's the epicenter of culture, history, and—our favorite—cuisine on the island, not to mention the home of a burgeoning world-class cocktail scene. If you're worried about visiting after the hurricane, don't be. Not only have amenities been restored pretty much everywhere but the locals could really use your tourist dollar right about now. Rebuilding is expensive, to say nothing of lost revenues from the time just after the storm, and the American government isn't doing nearly enough (not counting paper towels of course—don't get us started). Okay, politics aside, here’s our super-biased totally-not-exhaustive guide to San Juan and surrounding areas.

Editor's Note: Puerto Rico is part of America. If you're American (like all Puerto Ricans) you can visit without a passport. The currency is USD, your cell phone probably works, and most of the locals speak English. Speed limits may or may not be in mph (more on that below).
We fell into an InstaTrap™

First, Some Tips:

  • Rent a car. It’s possible to get around without one but not easy (Uber is still a little unreliable there). Also, some of the best parts of San Juan are technically outside of San Juan. We payed just over $100 for an entire week, with free shuttle service to and from the airport. We would have easily paid double or even triple that getting around otherwise. If you decide to take this advice, know that driving in San Juan can take some getting used to. With that in mind, here’s a extra side of advice with your advice: Check you car insurance. Fellow drivers in San Juan regularly ignore traffic laws (including red lights) and axle-busting potholes are prevalent. We’re not saying an accident is inevitable (we managed to return unscathed) but it’s certainly more likely here than say, rural Iowa, especially if that’s where you learned to drive. In most cases, your auto policy already covers rental cars. If it does not, consider getting the additional insurance from the rental agency or, better yet, a new car insurance company.

  • Freeway exits, roads, and especially side streets are often unmarked or—more confusing still—marked with a name wholly different than what your navigation app is telling you. Get used to visually following the map rather than relying on road names. You will make wrong turns. It’s inevitable. Take a breath and try again. Calculate an extra 10-15mins into your travel itineraries to account for this.

  • Sometimes speed limits signs are in mph, sometimes kph, often with no way to differentiate. When in doubt, follow traffic—terrible advice in any other setting.

  • Be wary of street parking in Old San Juan. Tickets there can be costly. Oftentimes curb color is all you have to go on (if that). When in doubt, ask a local. Nearby street vendors are a good choice, or maybe a police officer—terrible advice in any other setting. For our time/energy/peace-of-mind we usually opt for lots or garages.

The blue cobblestone streets of Old San Juan

  • Relax. We’re making it sound worse than it is. Be a little more vigilant that usual and you’ll be fine.

  • Learn a little Spanish. Even just the basics (hello/where is/how much/thank you/I'm sorry). Yes, it’s technically America and a fair amount of the population speaks perfect English (especially in the tourist areas) but there’s no harm in being prepared especially if you plan on venturing out to places like Piñones or Guavate—and you damn well should. In those places a little Spanish will be somewhere between handy and absolutely necessary. Before you launch into that red-faced pro-English rant, be reminded that the United States has no official language.

  • Puerto Rican people are incredibly kind and helpful. Be kind in return.

  • Service at restaurants, even rather nice ones, is slower and less attentive than it is on the mainland. This is NOT indicative or laziness or disinterest, and certainly not anti-tourist bias. It’s just a cultural difference in guest expectation, plain and simple. Don’t take it personally, don’t let it affect your gratuity, and for goddess-sake don’t fucking snap your fingers.

  • Tipping conventions are similar to those on the mainland (unless you’re a shitty tipper at home, then tip more). For non-Americans that’s roughly 20% at bars and restaurants.

  • Your American cell phone plan will likely be unaffected. We both have T-Mobile, which is notoriously spotty in rural environments, but we had 5-bar LTE almost everywhere, only briefly dropping out when hiking in the middle of the rainforest. Call your carrier to double check and make sure they know that PR is part of the United States. Of the two reps we spoke with, one did not. I could forgive that if they were in India but they were actually in Florida (I asked).

  • We stayed in a beautiful Airbnb in Miramar, which is a safe, walkable, quiet and historic neighborhood just slightly inland. We recommend the area but pretty much everywhere in San Juan is just a short drive to everywhere else. Condado is certainly the hip spot by the ocean. We found it beautiful but also packed with tourists. If you’ve never tried Airbnb before click here to use our code for a $40 credit towards your first trip!

  • We never felt unsafe in Puerto Rico but, as with all places you travel, don’t be stupid. San Juan is a modern city, in many ways damn near indistinguishable from the mainland, but poverty is still a problem and desperation drives people to do unfortunate things. Don’t flaunt your valuables, don’t walk around alone at night, and keep your stuff (phone, wallet, purse, backpack, etc.) in close proximity while in crowds. It’s also a good idea to take a couple photos and photocopies of your identification before leaving that you can keep in your room and in your luggage. That way, if you’re ever separated from your phone and wallet you’ll still have a fighting chance of proving you are who you say you are (we ignored this advice in the past and suffered dearly for it).

  • Drone flying in or near San Juan is a massive headache. The airports, helipads, national parks, and protected municipal sites all converge here to create an overlapping web of prohibited airspace. I contacted air traffic control on a few occasions to get permission, which they gave freely but with the caveat that I remain below 200ft, which in most of San Juan is barely above the skyline. Even at 200ft you’re sharing the sky with a considerable amount of low-flying air traffic making the experience nerve-racking nonetheless. If you’re new to drone piloting, the rules can be annoying but I encourage you to learn and follow them. Not only will you avoid potentially stiff penalties but you’ll be one less person making it worse for the rest of us.

  • Coqui frogs: You’ll hear them every night. They sound like insects but it’s not unpleasant (Lauren loved it). They’re the unofficial mascot of Puerto Rico.

  • Dear fellow white people: Just because the locals speak Spanish please don’t make the mistake of thinking you are basically in Mexico (we ran into this more than you’d think). Restaurants don’t bring chips and salsa to your table (they don't often do this in Mexico either, fyi). Tacos are also probably not on the menu. They also don’t have lucha wrestling. Puerto Rico is very much its own place with its own rich history and culture but if you need a proxy, the food and culture is much more closely associated with its neighbor Cuba than it is with Mexico (which, ya know, makes sense). Haven’t been to Cuba? Okay, think more Miami, less L.A. More plantains, less jalapeños. No judgement, new places are confusing for all of us and goddess knows we've made our fair share of cultural missteps. Just please take notice. If ya don't know, now ya know.

Pro tip: Get a coco frío every chance you get


Okay, now the fun part


Editor's Note: We love the advice of friends and fellow travelers when it comes to planning our trips but we never plan too much and neither should you. Use this guide as a jumping off point, a list of suggestions, but don’t be beholden to it. Most of these places were discovered by just walking around hungry and/or thirsty and chatting with locals. Set aside some time to do just that and let us know what you find!


  • Medella: This isn’t a place but the cheap beer that you will encounter everywhere. Learn to love it. It will become your water.

  • La Factoria: A must visit. If you’re researching Puerto Rico, I’m sure we aren’t the first to tell you that (and we won’t be the last). Unfortunately, the recommendation has likely been followed by “it’s where they shot Depacito!” Which is true, but it’s like saying you should see Django Unchained because that guy who sang “Blame It On The Alcohol” is in it. La Factoria having been the set for a fantastically forgettable music video (for an admittedly catchy but decidedly overrated song) is really the absolute last reason it should be on your Puerto Rico itinerary. Perfect cocktails made by world-class bartenders (who are all annoyingly handsome), searing hot live music and dancing, and multiple bars packed into a space that looks a little like an abandoned paint factory and a lot like the castle from Edward Scissorhands—these are the real reasons it should be on your itinerary. Tell them we sent you, provided you’re not a royal douche or a shitty tipper that is.

  • Jungle Bird: Another sickeningly sharp cocktail bar from the pros behind La Factoria. This one is considerably more tropical in nature, though calling it “tiki” would miss the mark a bit (not wrong per se, just incomplete). The philosophy is this: why recreate a façade (which is what tiki is) when we have the real thing, the source code, the genuine article? It’s not a reaction against tiki—which is a beautiful illusion, but an illusion nonetheless—just an appreciation for all the authentic beauty they have at hand actually being in the Caribbean. Native Taíno motifs and iconography prevail. They are, however, rendered in neon. Also, come hungry. Their small kitchen, under the direction of the insanely talented and terminally hip Chef Paxx (just named one of Food & Wine's Top 10 Best New Chefs), churns out some next level Asian-inflected traditional Puerto Rican food. Even if you come full, the smells ushering forth from the kitchen will convince you otherwise.

  • La Placita del Santurce: Open air produce market by day, giant block party by night. Outdoor drinking, rows of restaurants catering to drunk people, live salsa music and locals who know how to dance to it (and a few tourists who do not). Weekends are best.

  • Birthplace(s) of the Piña Colada: Okay, this is a twofer. Both Barrachina and the Hilton Caribe claim credit. They’ve even both erected plaques. For our money, the Hilton Caribe seems to have the stronger case. Their origin story also predates Barrachina’s by several years and it’s a little easier to confirm. Unfortunately, the Hilton Caribe was undergoing massive renovations when we were in town so we didn’t even get to try theirs! Barrachina’s come from a slushie machine but they were still hard to hate because piña coladas are delicious (see above for our thought on school and being too cool and so on and so forth). It's also a damn cute place. We only dropped in for a quick drink but it would be a nice spot to have a meal.

  • Pitorro: Puerto Rican moonshine, distilled at home and usually strong enough to strip the chrome off a trailer hitch. Clear distillate, ron caña, is usually placed in a vessel with some combination of fruit, nuts, berries, even meat, and buried for a predetermined amount of time. This not only keeps it cool in the tropical Puerto Rican heat, but also away from the prying eyes of the ATF and the taxman. Again, this is illegal to sell, but if you make the right friends you’ll have no trouble getting a “Puerto Rican handshake” (no one calls it that, that’s a thing I just wrote). To improve your chances, make a friend or two in the mountains (around Guavate, for instance). Pitorro is, after all, called lágrima de monte (tears of the mountain). To really improve your chances, take a trip to Añasco AKA La Ciudad Donde los Dioses Mueren (The City Where Gods Die). This is the epicenter of pitorro production on the island. If you don’t think we have a trip planned there in the near future you are sorely mistaken.


  • Casita Miramar: This place is a must visit. Exceptional food and some of the most professional staff we’ve encountered anywhere. Very cute converted house. Always busy. Expect to wait in a cramped foyer, but you can order drinks from the host while you do.

  • Gusto Coffee: Cute place for coffee and a simple breakfast or lunch. Open, airy, great patio. Nice place to get a little work done (if ya have to).

  • Pinky’s: Hip little breakfast/lunch spot with fun menu and quick service.

  • MASA: Fantastic breakfast, lunch, or dinner. Huge portions. Professional service. Highly recommended

  • El Churry: With all do respect to Taco Bell’s 4th meal, this is actually the best drunk food we’ve ever encountered (and the owners know it). Started in 1998 as a simple food truck, the place is now a damn institution in PR, with several more trucks and even a couple brick and mortar locations. Everyone we talked to, from college student to grandmothers, got downright sentimental when talking about El Churry. We recommend the mixto sandwich, a combination of chicken and churrasco beef, seared on a flat top then stuffed into a housemade pan sobao roll (Puerto Rican sweet bread) and topped with lettuce, tomato, potato sticks, and mayoketchup (the official condiment of Puerto Rico, guess what’s in it).

  • Piñones: Chinchorrear is a verb Puerto Ricans invented to describe what happens here. It, roughly translated, means spending the day with friends visiting fried-food kiosk after fried-food kiosk (called chinchorros, hence the verb form) getting stuffed on bacalaítos (salt cod fritters) and alcapurrias (plantain/taro/yucca fritters stuffed with beef or crab) and more while washing it all down with cheap beer (probably Medalla). If it happens to play out just a few steps from the beach—as it does in Piñones—all the better. Organized excursions of this nature are called chinchorreos and, if you go on the weekend, you’re bound to run into a few. They can get quite elaborate, including everything from custom t-shirts to chartered tricked-out school buses, sporting chrome rims, neon, and external speakers blasting a combination of Top 40 and Bomba. Remember that thing we said at the beginning about blazing your own trail and not taking everything we say as gospel? Forget that advice for a moment and take this advice instead: Fucking go here. Plan to spend an afternoon. Our favorite place in all of Piñones (and maybe the whole world for that matter) is Kiosko el Boricua.

  • La Ruta del Lechon: AKA Guavate AKA "The Pork Highway". Okay, this is also a must-visit (unless you’re a vegan, in which case you might want to rethink Puerto Rico entirely). Located about an hour south of San Juan proper, in the mountains of Cayey lies a stretch of RT184 that is populated almost exclusively with open-air restaurants that specialize in spit-roasting seasoned whole pigs. They are portioned, to order, with a machete and served with a number of traditional sides, including rice with pigeon peas, cooked plantains, and housemade blood sausage. Be sure to ask for a generous helping of the skin. It’s like peanut brittle but made of pork so yeah.


  • Balcalnero el Escabron: This, according to everything we’ve read, is the jewel in the crown of San Juan beaches. And it is nice, don’t get us wrong. Ample parking, clean bathrooms, great views. But all PR's beaches are nice. If you’re in the area, cool, check it out. Otherwise, just find the ocean. It’s never far.

  • Condado: Gay men in speedos (or less) will sometimes outnumber the people who do not fit this description and I put this firmly in the “pro” category. The only negative here is that, male or female, you may feel more self-conscience than usual as they are all—literally all of them—paragons of physical perfection and they know it. They are also fun and welcoming and they play good music. There’s also usually a guy or two selling hollowed-out pineapples filled with booze (just ask the people carrying hollowed-out pineapples where they got 'em). This is expressly prohibited but no one seems to care. Be wary of beachside hotel bars though. They can get real nasty if they find out you’re not a guest (our ratty towels gave us away).

  • Luquillo Beach: We dropped into this one on our way back from El Yunque rainforest. It’s beautiful (again, they all are), quiet, and you can usually park for free right beside the sand. It’s also one of the few places anywhere near San Juan where you can freely fly a drone (if you’re into that sort of thing).


  • El Morro: This is likely the most recognizable landmark in San Juan and perhaps all of Puerto Rico. More formally called “Castillo San Felipe del Morro” or “Fuerte San Felipe del Morro,” construction on this military fort/citadel began in 1539. It was then in continuous use as a coastal stronghold until 1961! It even played an important role in WWII under the control of the U.S. Army. It is now part of the U.S. National Park System. It’s also a UNESCO World heritage Site and is listed on the U.S. National Register of Historic Places. It is a very popular place to fly kites, which can be purchased from several vendors on site. DO NOT set off a drone while on the premises. The National Park Service has been very litigious as of late.

  • El Yunque Rainforest: The only tropical rainforest in the U.S. National Forest System. When we visited, they were still bouncing back from the hurricane (the gov’t shutdown certainly didn’t help matters) so a couple of the more popular parts of the forest were closed for repairs, including the main visitor’s center (El Portal) and the path to La Mina falls. That being said, there’s still plenty to see and do, including multiple waterfalls and that are accessible just off the road. The Yokahu observation tower is also pretty rad and easily accessible. Be sure to drop into the temporary visitor’s center in Palmer (#54 Calle Principal) before entering the forest to watch the informational video narrated by Benicio del Toro :) Also, if you’re really cool like us this is where you’ll get a patch or button to decorate the jean jackets you have set aside just for this purpose. Unlike National Parks, National Forests are much more permissive of drones. As always though, be respectful and mindful of local restrictions.

  • Bacardi Distillery: Before you start bellyaching re: “the vodka of rums lol i so funny” know that we are advocating the experience and not necessarily the product (they’re not paying us enough). That being said, while we don’t often reach for Bacardi Superior (“silver”) these days, some of their more premium bottlings are genuinely worth sipping (the 10yr is pretty solid if memory serves). So go kick rocks if you’re too cool for school, or worse yet, think we should be. We love school. Okay, back to the distillery: the campus is fucking beautiful, the distillery itself being housed in a monolithic Art Deco skyscraper of sorts. I’ve always loved Bacardi’s aesthetic, which is one of the key reasons it, and unflavored Stoli for the matter, usually have a place amongst my bottles. On the design front, they do not disappoint. Furthermore, the history of Bacardi is truly fascinating, which is an aspect of booze we are particularly drawn to—like moths to a flame. You know how much Carolina rice wine we’ve consumed just because of the cool story? Shit is gross. Anyhow, the distillery is located in Cataño, just across the bay from San Juan. If you took our advice and rented a car you can easily drive there, but taking the $0.50 ferry from San Juan harbor is more fun.

Instagram Traps:

  • Umbrella Sky Project: A portion of Calle Fortaleza that has been covered in colorful suspended umbrellas. It’s an Instagram trap of the highest order, but the philosophy behind it was to remind PR that the hurricane cannot strip away her color. We can get behind that. Makes a killer caption to boot. Shit, see what they did there?

  • Feeding the pigeons at Parque de las Palomas: Located in front of Capilla del Cristo (a beautiful 16th century church worthy of visiting in its own right). We’ve encountered these “give me a dollar and I’ll let a bird shit on you” type outfits before but this one was next-level. I’ve never seen so many damn pigeons. Apparently, the adjacent old-as-time stone wall was built specifically to house nesting birds. That or the designers frigged up big time. Anyhow, for $1 you’ll be given some birdseed which will immediately cause like 200 pigeons to descend upon you, landing on the length of both arms and even your head. Any exposed skin will get some minor scratches. You’ll almost certainly get dookied on. Bring wet wipes and have your cameras ready. We recommend getting familiar with burst mode.

Bonus Round: Vieques

Okay, our shooting schedule in Puerto Rico started to buckle under its own weight and we were forced to forego Vieques at the last minute. However, we did a little (okay, a lot) of research in preparation for our unrealized excursion and someone might as well benefit.

For those of you who don’t know, Vieques is a small island in Puerto Rico that, in addition to having an airport, is also accessible by Ferry (which is around $36USD). It’s filled with beautiful beaches (included a black sand beach, Playa Negra), wild horses, and the brightest bioluminescent bay in Puerto Rico. Though some make it a day trip, we think if you’re going to go through the trouble of getting there, you should at least spend the night. In any case, transportation should be your primary consideration, as Uber is pretty much non-existent and traditional taxis are expensive and somewhat difficult to find. If you do go this route, we recommend finding a driver you like and asking for his personal phone number. This is now your driver. The best option, in our opinion, would be to rent a Jeep. Golf carts and scooters are also available but the savings is minimal and much of the island is unpaved i.e., you ain’t getting there on a scooter. As far as tours of BioBay (technically, “Mosquito Bay” and we hear for good reason) Black Beard Sports seems to be a safe bet. These tours fill up fast though, so be sure to book yours in advance. Have fun. Rub it in.


Okay guys, hope that helps! Hit us with a tag or drop us a line if you found any of this info useful. As always, let us know what other amazing stuff you discover!