Despacito in San Juan, Puerto Rico: Itinerary for a Long Weekend in Viejo San Juan

Important Note – This blog post was written before Hurricane Maria devastated the island of Puerto Rico. If you are interested in helping Puerto Rico rebuild, here many options for contributing.

Our Trip

I’ve been listening to Luis Fonsi’s “Despacito” all summer long and because of the gorgeous scenes (and Daddy Yankee) in the video that I watched a thousand times, I started obsessing over visiting Puerto Rico. So, after a bottle of wine and a couple of weeks of research, I booked a long weekend in Old San Juan for Labor Day weekend.

Getting There

For American citizens who don’t have passports, Puerto Rico is a great option for experiencing the Caribbean with just a drivers license. As there were no direct flights to San Juan from CLE, it took us about 5 hours flying time via Philadelphia with American Airlines. United does offer a seasonal, direct flight to San Juan to service spring break cruisers heading for San Juan’s port from CLE.

It was easy to find a cab to Old San Juan for about $20 at the airport and pre-arranged transportation is just as cheap. Uber is ideal for traveling around the island and when returning to the airport but drivers are not permitted to pick you up on airport property.

Where to Stay

If you’re looking for a hotel within walking distance of restaurants and nightlife, I’d recommend the modern, major brand hotels of Condado or the small, boutique hotels of Old San Juan.

In the Condado area which has beach access and is just outside Old San Juan, I like the Condado Vanderbilt, a 5-star, super luxury hotel with a beautiful beach and the San Juan Marriot Resort and Stellaris Casino, a large property with a resort style pool and yep, you guessed it, a casino!

For this trip, we chose La Terraza de San Juan in Old San Juan. La Terraza is a 26 room, boutique hotel built in the 19th century and is located in the middle of the action. We didn’t get a chance to use it but the hotel has a small plunge pool on the rooftop and great views from its terrace and a killer happy hour.

Our "Superior" room was a little smaller than we normally go for, due to the architecture. but it was clean, cool (the a/c and fan saved us in 90 degree heat!) and had everything we needed.

The staff were super knowledgeable about the area. They helped us vet our list of things we wanted to see and gave us their own recommendations to add – I can’t speak highly enough of their team.

Also up for consideration in Old San Juan should be the Hotel El Convento. This property was unfortunately fully-booked during our trip and after walking by, we could see why. Rooms with balconies, a beautiful courtyard with 2 restaurants and privileges at the El Convento Beach Club at its sister properties – I’m adding this one to my “must stay” list.

If you are looking for more of a beach vacation, Farjado on the Northeast tip of the island is for you. We weren’t overly impressed with the public beaches in Farjado, but there is a fantastic Waldorf Astoria property, El Conquistador Resort, which has access to a private island and its own beach area. If you are planning an excursion to the islands of Culebra or Vieques, Farjado’s port provides direct access.

What to See

We covered a lot of ground during our trip despite skipping our Sunday morning plans (pro-tip: pace yourself when drinking rum). This list could go on and on but these are some of our top picks for a weekend in San Juan:

Old San Juan

Old San Juan is an Instagram dream. The cobbled streets and colorful, colonial buildings are picture perfect and there is so much complex history surrounding the city. We loved visiting the El Morro and Castillo San Cristobal forts and just $5 per person gets you entry to both - you can easily do both in a morning. El Morro is the larger of the two forts and they recently installed a sea level path that takes you all the way around the outside of the fort to the San Juan Gate. This was one of my favorite spots as a local organization had created a cat sanctuary near the path so there were super cute kitties sunbathing on the rocks next to the 500 year old fortress #crazycatlady.

Nearby, you can take in the beautiful governor’s mansion, La Fortaleza, and properties owned by the Ponce de Leon family, descendants of the Spanish founder of the settlement in San Juan.

Essentially anything you come across in Old San Juan is interesting and worth exploring. You’ll have the best time just wandering up and down the main streets for an afternoon and immersing yourself in culture…and, of course, rum! We walked a ton but there is a free trolley running across Old San Juan if you need it.

El Yunque National Forest

We started our driving tour of the Northeast part of the island with El Yunque National Forest, the only rainforest in the U.S. National Park system which is located about 50 minutes from Old San Juan.

The 28,000 acres of forest were very easy to navigate – we spent a couple of hours there in the morning, driving up the Luquillo Mountains and taking pictures at the suggested stops before parking up to hike La Mina trail. This trail is the most popula rdue to the waterfall swim at the end and takes about 45 minutes each way. While the way down to the falls was quick, walking back up all of the steps was a challenge in the September heat! It felt like hours but it probably took just over an hour or so – if you have small children or a knee injury, I would give it a miss!

If you don’t want to rent a car, tours with transportation from San Juan are offered to El Yunque.

Piñones

Before returning our rental car, we drove along the coastal road into Piñones. Piñones is just East of the airport in San Juan and has a newly constructed boardwalk, surrounded by a mangrove forest. Kiran’s favorite part of Piñones was the food – we had to stop at one of the many roadside stands for pinchos (shish kabob) after smelling it cooking during our drive through the area!

Casa Bacardi

Due to the fun we had on Calle San Sebastian the night before, our last full day in San Juan got off to a late start. Luckily though, by sleeping off our rum hangover, we missed a rainy morning and still made our afternoon tour of Casa Bacardi. You can take the ferry over from San Juan near the cruise port for $.50 per person but we opted for a cheap and quick Uber.

*Hair of the Dog, by Royal Decree of Spain*

I generally don’t enjoy tours like this – they never seem to be worth the money– but this was one of the highlights of the weekend for both of us. By the time we arrived, the weather had cleared up (as had our hangovers!) so we spent the afternoon touring the Cathedral of Rum, participating in a tasting of 6 Bacardi rums with a fantastic brand ambassador and lounging outside the bat-shaped pavilion with our strong Cuba Libres. On the tour, the guide mentioned that a King of Spain once proclaimed that a shot of Bacardi Superior (that’s the clear one) could cure any sickness and I’ll say with certainty that hair of the dog in this case turned my day right around!

La Perla

After catching our second wind at Casa Bacardi, we headed back across the bay and walked along the old city walls to see the La Perla neighborhood. Separated from Old San Juan by the city wall, this unique neighborhood was the location for the “Despacito” video. We heard mixed opinions about visiting the neighborhood. Some told us about how it has been historically marginalized and ridden with crime, unsafe for tourists. Others told us how the neighborhood had cleaned itself up and tourists were welcome. We didn’t get chance to walk down the hill and explore but we did get some great pictures of the area from both forts. If you plan to visit, I’d recommend doing some more research about what you might want to see and visiting during the daytime.

Food and Drink

Street Food - Kioskas de Luquillo

Starving and dehydrated (pro-tip: don’t hike in 90 degree weather on an empty stomach) after our morning at El Yunque, we headed out of the forest for lunch at the Kioskos de Luquillo. This beach side spot has been featured on the Food Network and Travel Channel and is a row of about 60 miniature restaurants selling specialty Puerto Rican, Caribbean and seafood dishes. We chowed down on empanadillas (beef turnovers) and alcapurrias (stuffed fritters) for just a couple of dollars. Be prepared to pay in cash only and bring small bills if you have them – we encountered some tourists struggling to pay for their meals with a $10 bill, which should give you an idea of how cheap the eats are!

Mofongo and Pina Coladas

We wanted to do at least one upscale dinner after a weekend of street food so we made reservations at Barrachina on Saturday night. This restaurant serves traditional Puerto Rican fare in a sophisticated indoor/outdoor setting. Barrachina’s claim to fame is being the birthplace of the Piña Colada – apparently, Barrachina’s bartender don Ramon Portas Mingot came up with the recipe in the early 60’s and despite whether that is true, it was actually the best Piña Colada I’ve ever had!

Although the food was delicious at Barrachina, if you’re looking to sample Mofongo (a staple Puerto Rican dish made with mashed plantains) or other local treats in a more casual environment, everyone we met raved about El Jibarito. This restaurant was a couple of doors down from our hotel and Café Puerto Rico on the Plaza Colon was also highly-rated and has a great patio.

Unfortunately we didn't make it in but I was dying to try out Señor Paleta, an ice cream shop with a quirky Instagram account, especially considering how hot it was during our stay!

Indian Puerto Rican Fusion

We weren’t sure how exactly one would create Puerto Rican/Indian food but we decided to give Pani Agua a shot on our last night in San Juan. Located on the Plaza de Armas, Pani Agua (or “Water Water”) serves food, hookah and hundreds of different types of mojito. We sat at the bar and ordered the blackberry mojitos and inhaled a couple of Caribbean spiced chicken Kathi rolls which I’d highly recommend.

Late Night Food

While we waited to check into our room upon arrival, we discovered a couple of little restaurants that served food all the way into the late evening. Having made a mental note of what we might need for a night of rum drinking, we grabbed a pizza at La Nueva Focaccia when we returned from La Placita. The owner was a great guy who chatted to us about life in San Juan and things we shouldn’t miss during our stay.

Directly across from La Nueva Focaccia is La Guerita – a Puerto Rican influenced taco bar. This was our very first stop in Old San Juan and not only were the Cochinita Pibil and Al Pastor tacos exactly what we needed after our flight, yet another squad of friendly bartenders was on hand to get us acclimated to Puerto Rico – this time through current music trends - I’ll blame them for my new obsession with Bad Bunny.

Beer and Rum

Is there anything better than patio drinking?

Given that Bacardi, the world’s best selling rum, is produced in Puerto Rico, we expected that it would be popular at bars across the island but we discovered another local rum that seemed to be a pretty close competitor – Don Q. Don Q was founded in Ponce, PR and was relaunched in the U.S. in 2006 (although I haven’t seen it in Ohio, sorry Buckeyes!). We switched back and forth between Bacardi and Don Q all weekend – both were tasty and surprisingly cheap!

We also enjoyed locally brewed Medalla Light (comparable to a domestic light beer) for less than $1.50 anywhere on the island and Magna (similar to Heineken) for just a dollar more.

Nightlife

On our first night in San Juan, we ventured out to La Placita, a street party in the Santurce neighborhood of San Juan, set against the backdrop of the Mercado Santurce.

We ate delicious appetizers at a restaurant I’ll never remember the name of (which kills me because we are still talking about the food!), listened to some live music and later on in the evening, posted up at local club for some Don Q rum and reggaetón.

*La Taberna Lupolo, Spanish for"Beer Heaven"*

Since Friday night was all about La Placita, after dinner on Saturday we headed out to Calle San Sebastian in Old San Juan. Our hotel bartender had told us that this street was known for its bars and it was truly the place to be! I was dying to check out La Factoria, the bar where some of the video for the Despacito had been filmed. It was a mission to find the entrance to this speakeasy – we had to ask a bartender at another bar who gave us a description of the bouncer at La Factoria and told us to ask for him by name – once we finally got in and took 1,000 pictures, it was well worth the hunt!

Another of our favorites was La Taberna Lupolo, a beer hall serving up almost a hundred craft beer options in an open air courtyard – Kiran’s idea of heaven.

On our last night in San Juan, we spent most of the evening drinking Don Q at Café Teatro Rivera Hermanos, listening to an awesome live band who played acoustic versions of everything from Justin Bieber to the Gipsy Kings. Upon figuring out we were American, the bar staff there insisted we have a fire-blown shot of Bacardi 151, since it is no longer sold in the rest of the U.S. and they felt sorry us :)

Travel Agent Pro-Tips

1) Learn a little Español or at least download Google Translate

This was pure ignorance on my part but I expected that everyone would speak English and menus would be in both languages. Shame on me. With our limited Spanish, we did struggle a little bit in some places to communicate effectively. Some of our Uber drivers and staff at restaurants that were less popular with tourists spoke no English so there was a lot of pointing and a lot of Spanglish but nothing we couldn't overcome. We actually felt quite ignorant that we hadn’t bothered to prepare appropriately or at least downloaded the Google Translate app. We were usually the only American tourists in the bars and restaurants we visited so it made our lack of Spanish even more obvious. When I return to the island, I plan to be a lot more competent in my language skills!

2) “Man, its HOT!” - the Understatement of the Year.

San Juan is the hottest place I’ve ever been. Bring your sunscreen, reapply it regularly and wear a hat – walking around without one through the streets of Old San Juan was no bueño! I did not see any mosquitoes while in the city but we definitely needed bug spray in the forest.

3) Don’t Drive Yourself Crazy

Driving and parking in Old San Juan is terrifying. With narrow one way streets, tight turns and no parking for non-residents, my advice is to pick up and drop off your rental car in Condado. The Sheraton in Old San Juan near the cruise port does have rental cars but they didn’t have the class of car we wanted and we would still have had to deal with Old San Juan parking. We had a ton of fun roaming around the island in our Jeep Wrangler with the top off – it just made our experience even more memorable.

4) Plan Ahead

A long weekend in San Juan felt like a week because we really packed our schedule with things we wanted to see and do. Some things like the Casa Bacardi experience had to be reserved in advance so make sure you book those tours with your agent before you arrive in Puerto Rico.

Our cell phones did work and we were able to use our data without a problem but Google and Apple maps weren’t always great at directing us. On foot it wasn’t really a problem but we found that when driving around, some of the street signs didn’t match up with the street names on our apps and we missed a LOT of turns. You can download Google maps to be used without wifi for a specific area, which was helpful when we didn’t have reception in the forest.

5) Be Smart

Sure, its the Caribbean, its beautiful, the people are friendly but "be smart". I tell clients this no matter where they travel and Puerto Rico is no exception. Use the safe in your room, don’t wear flashy jewelry or walk around with wads of cash – things you’d shouldn't do in any city. There were some places we were advised not to walk around in late at night (those were wayyyy outside Condado and Old San Juan) but we never felt unsafe walking, driving our rental or riding in Ubers. There seemed to be a heightened sense of political sensitivity, as there is no matter where you travel these days, but we felt so welcome and comfortable in all of the places we visited. The people of Puerto Rico were absolutely lovely!

This post is intended to be a short recap of our stay with a focus on our itinerary and things to do in the area. For a more in-depth review of La Terraza de San Juan, let's chat about your needs and whether this property would be a good fit for you and your group.

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