Digital Nomad Cities – San Juan Puerto Rico

categories: caribbean travel, USA Travel

When I checked into the Hotel Convento in Old San Juan, the desk clerk asked me if I was there for business or for pleasure. Why do I need to choose? On a video call today, one co-worker thought I was working on my vacation… which would be bad. But I was really vacating on my “workation.” We don’t even have the language to describe that yet.

During the pandemic, many knowledge workers learned they could work productively remotely. But does that really need to be from your home office?

When you think that your manager might be OK with you working remotely from other than your own home office, where would you go first to try it out? Some people would get on a plane and head to some digital nomad hotspot like Chiang Mai, Thailand, but I am going to suggest you do what I did and spend your first week in Old San Juan, Puerto Rico, instead. This is one of the best places to start working remotely.

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Why Work from Puerto Rico

Puerto Rico – It’s in the USA!

My current day job has a “work from anywhere” policy, but anywhere is a bit of an exaggeration. There are some places where they don’t want a laptop with sensitive corporate information to end up. Frankly, there are some destinations they would be OK if I never went to even on my own time. With that said, I can work from much of Europe, most English-speaking countries, and half of Central and South America. All I need to do is:

  1. have permission from my boss’s boss’s boss
  2. have whatever visa I need to be able to legally work in that country.

When you are a big multi-national company, you can’t really turn a blind eye to people working where they can’t legally do so.
But… Puerto Rico is part of the United States. I didn’t need more than my manager’s permission. I also don’t need a visa to work in San Juan, any more than I need one to work in San Jose. I don’t even need a passport to get to Puerto Rico. You don’t have to clear customs when you fly from the USA… because you never left American territory.

Original Main Square of Old San Juan

Original Main Square of Old San Juan

Puerto Rico is on New York Time… sort of

Puerto Rico is in the Atlantic Time timezone, which is an hour ahead of New York and the east coast of the United States, but it does not observe daylight savings time. That means that for more than half of the year, from spring to autumn, it is essentially the same timezone as Boston, New York, NYC, Washington D.C., and Miami. That can make it easy to work with colleagues on the East Coast. Since I normally live in California and most of my co-workers are on Eastern Time, it was actually more convenient for my manager for me to work from Puerto Rico than from home.

Contrast that with the temptation to get on a plane and fly to Chiang Mai, Thailand, or some other far-flung destination. Thailand is 11 hours ahead of New York City. Much of Europe is 6 hours ahead of the east coast. Plan on having some meetings in the middle of the night if you want to work there. Also, your boss has to really trust you that you can work without supervision before they will OK that move.

Old San Juan

Puerto Rico Does not Feel like it is in the USA

One of the best things about Puerto Rico is that it does not feel like it is in the United States. Sure it has some of the same stores and is very easy and comfortable even for monolingual Americans, but it also has a Caribbean flair. When I was dropped off by my Uber at Hotel Convento, where I stayed at the start of my visit, the first thing I heard was Caribbean music wafting from the local bars and cafes.

Iguana at El Moro

Puerto Rico is in the Tropics

There is very little of the United States in the tropics. Hawaii is the only state in the tropics… although Florida would like to think it is. Other than Hawaii, if you want to stay in the USA and be in the tropics, you need to go to the U.S. Virgin Islands, Puerto Rico or American Samoa, Northern Mariana Islands, and Guam. Guess which one of those has the best Piña Coladas.

If you live in the eastern half of the United States, Hawaii is a long way away, while Puerto Rico is not much further than Florida. This is beach weather. It is warm all year round.

Why work in San Juan Puerto Rico

San Juan has more history than the rest of the United States

San Juan was founded as the capital of Puerto Rico in 1519. That’s 46 years before St Augustine, Florida, and 88 years before Santa Fe, New Mexico, or Jamestown, Virginia. When you visit Old San Juan, you can walk on cobblestones trod by conquistadors, visit the house that Ponce de Leon built but never lived in (before he searched Florida for the fountain of youth), or the cathedral where he was buried (guess he never found that fountain of youth). The Cathedral of Old San Juan is the second oldest in the Americas, second only to the one in Santo Domingo.

Old San Juan

San Juan has Nightlife

If you are going to work in the same timezone as the home office in New York City, then when work finishes, you don’t want to be someplace where the city has closed down and gone to sleep. You want to work someplace where the city is just waking up, and Old San Juan is one of those places. It has bars and nightclubs, particularly on the Calle de San Sebastián. This is not just where tourists come to party, but where Puerto Ricans come to enjoy the nightlife.

There are well-known cocktail bars like La Factoría, the beer bar, and bottle shop La Taberna Lúpulo and places like Cafetín where you can get a $5 Mojito.

San Juan has Food

I stayed in Old San Juan for a week and never went back to the same restaurant twice… and still did not have enough time to explore all the great restaurants in the neighborhood. You can find good pizza at places like Pirilo, food trucks down by the cruise ship docks, or go for a more traditional Puerto Rican dish and order mofongo and any number of places.

At Casa Luna Rest, I learned to make my own mofongo, which starts with mashed plantains. At Deaverdua, I tried fried breadfruit for the first time. Yes… it tastes like bread. At Barrachina, the home of the frozen Piña Colada I tried… of course… a Piña Colada.

I ate an amazing french toast combination breakfast (strawberry cheesecake french toast and blueberry compote french toast) at Mercado La Carreta one morning (sponsored by Discover Puerto Rico) for breakfast and then another morning a traditional Mallorca (stuffed Puerto Rican sweet bread) at Cafetería Mallorca.

For real foodies, I also made a visit to the restaurant Cocina Abierta in the nearby Condado neighborhood (also sponsored by Discover Puerto Rico). This restaurant is working to change the Puerto Rican Food scene. Puerto Rico imports 85% of its food, but this restaurant is part of a movement to change that. They only use local ingredients and turn those into some amazing dishes like tacos al pastor with oyster mushroom for “meat”, star fruit pico de gallo, and breadfruit tacos pictured above.

Old San Juan tour

Skinniest Building in Puerto Rico

San Juan has Activities

When you have a day off, you can take advantage of a range of activities in the city. I did the El Morro Fort and Old Town Walking Tour, which explored from the harbor area up to the old El Morro Fortress. We learned about the origins of Puerto Rico’s wealth, the privateer Miguel Enríquez, the Cathedral and the origin of the name “Puerto Rican”, the miracle that happened at the chapel of Christ the Savior, the Dutch invasion of Old San Juan in the Eighty Years’ War, and life at El Morro… just to name a few things.

I was sponsored on this tour by Get Your Guide, and the tour was done by Patria Tours. It was a great overview of the old city.

Discover Puerto Rico also set me up on a Classic Old San Juan Food Tour with Flavors food tours of old San Juan. Come hungry for this tour as it involved a breakfast pastry, the main course… another main course where we made our own mofongo, and gelato. Along the way, our guide Marjorie Ana told us more about the history of Puerto Rico and also pointed out some of her favorite restaurants in the city. Do this tour on your first day!

Many tours of Puerto Rico depart and return from San Juan, so on your days off, you can easily get to other parts of the island.

Where Digital Nomads Should Stay

There are numerous options for staying in San Juan for digital nomads. I have worked from both Old San Joan and from the beach area of Ocean Park in a co-living, co-working space run by the site Offsite.  Old San Juan offers hotels, boutique hotels, and a number of Airbnb properties.

Hotel Convento

As mentioned above, my first 4 nights were at Hotel Convento in the heart of Old San Juan. This hotel, which is a former convent, is across the street from the San Juan Cathedral. Although I don’t think the nuns had the rooftop pool and hot tub that the hotel now has.

When I am looking for a place to work from, I am looking for price, location, internet speed, good wi-fi, and good work surfaces like a desk. Hotel Convento is not the cheapest hotel in the area but was a pretty good place to work for half a week. The internet speed was fine, although the wi-fi signal was stronger in my room than it was in the common areas like the rooftop deck. When I was there, the wi-fi in the central courtyard was not working.

My room was large and comfortable, with a table, a desk, and a comfortable chair where I could work. There was a wi-fi repeater in my room which had great wi-fi coverage. The internet speed for the hotel was generally good except for the evening that I spent there during Hurricane Fiona which I suspect was busier than usual as people could not go out. As a hotel to ride out a hurricane, I felt pretty safe. It is an old stone building with very thick walls and serious shutters.

The hotel has two restaurants. I ate at the one in the central courtyard, which was good, although the service was not what I would call fast. There is also a bar in the same area. The food included risotto, pasta, hamburgers, and other not specifically Puerto Rican food.

Villa Herencia Hotel

I spent the second half of my stay at the boutique hotel only two doors down from the Hotel Convento. While it is in the same neighborhood, the Villa Herencia Hotel is quite different. This is a hotel that is also in a historic building but with a bit more style. This hotel does not have a restaurant. It only has 10 rooms.

My room was comfortable but much smaller than my room at Hotel Convento. The only place to work in the room was on the bed. It did have air conditioning which was pretty much essential when I visited in September as the temperatures were in the 90s with high humidity. During my stay at Villa Herencia Hotel, I spent more time working from the common room or from the rooftop terrace.

Here the wi-fi and cell coverage were actually better in the common room or on the roof, so both were great places to work. I tended to work in the common room during the heat of the day and on the roof during the morning and evenings. Some other guests would come into the common room for ice, cold water, or coffee, but I largely had the place to myself.

Other places to stay in Old San Juan:

Hotel rating cost    
EL Colonial Adults Only 9.2 $$$$   Book Now
Palacio Provincial – Adults Only 8.9 $$$$   Book Now
Hyatt Place San Juan 8.9 $$$$   Book Now
Villa Herencia Hotel 8.6 $$$$   Book Now
CasaBlanca Hotel 8.3 $$$   Book Now
Navona Studios 8.1 $$   Book Now
Hotel El Convento 8.1 $$$$   Book Now
Hotel Miramar 8.1 $$   Book Now
Dreams Miramar 7.7 $$   Book Now
The Tryst Beachfront Hotel 7.5 $$$   Book Now
The Ivy Hotel 7.5 $$$   Book Now

Outsite Puerto Rico

If you are not familiar with Outsite, it is a co-working and co-living space. It is in some sense an upscale hostel where typically everyone has their own room, their own bathroom, a desk, and high-speed internet. Each also has a shared kitchen, laundry, and at least one co-working space. 

The company that runs Outsite has locations in about a dozen places at this time. One of them is in the Ocean Beach area of San Juan, between Old San Juan and the airport.

I stayed in the Outsite Puerto Rico for a few days after a conference in San Juan and it is a great place to park yourself and get things done. When you check in, you get invited to a Whatsapp group so you can exchange info with others who are staying there. When I was there a group of us went out to Sunday brunch at one of the restaurants within a 15-20 minute walk from the Outsite.

If you stay here, my favorite local restaurant is Barbacoa Puerto Rico at 2422 C. Loíza. They have a great BBQ menu including a delicious smoked chicken. They also have good desserts. I liked both the carrot cake and the key lime pie.

It took me two visits to San Juan before I was able to stay in the Outsite Puerto Rico. My previous visit to Puerto Rico was just after Hurricane Fiona hit the island and the neighborhood where the Puerto Rico Outsite is located was without power although the Outsite itself has a generator.

Co-Working Spaces

You never know how hotel internet will be, but I had a backup plan. There are a number of co-working spaces in San Juan, Puerto Rico, and two in Old San Juan. The one day I was having problems with my corporate VPN, I almost relocated to one of Lunaspeiz or Piloto 151 Coworking at Old San Juan, which are only a couple of blocks away from the neighborhood where I was staying in Old San Juan. If you work from a co-working space, you will add additional expense unless, like the Offsite location I mentioned above, it is a co-working and co-living space, but it is good to have the option if you need it.


I spent a week enjoying Puerto Rico. I learned the streets of Old San Juan. I took tours and sampled its food. I did all this without taking a vacation day. Maybe working remotely from Puerto Rico should be in your plan for next year. If you can work from anywhere… shouldn’t you be here? 

 Digital Nomad Cities - work from Old San Juan Puerto Rico #travel #digital-nomad #work-remotely #puerto-rico #san-juan #travel #vacation #trip #holiday

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Chris Christensen

by Chris Christensen

Chris Christensen is the creator of the Amateur Traveler blog and podcast. He has been a travel creator since 2005 and has won awards including being named the "Best Independent Travel Journalist" by Travel+Leisure Magazine.

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