Workation
Anyone who’s followed me or knows me in person knows that I love cigars. I won’t go into my personal history with cigars, which has been a life-changing passion going back to about 1997; that is another story for a different blog. When I had an opportunity to do a one week ‘workation’ in 2024, it was my passion for the leaf that took me to Nicaragua. For the last couple of years, I can take one week per year and work remotely in addition to my annual paid time off. The first year I went to Guatemala, and this (second) time to Nicaragua. It’s essential that I do the workation in a time zone that roughly lines up with Vancouver’s. I’ll probably explore most of Central America this way.
But where in Nicaragua? Granada was the obvious choice, as it is so charming, but I decided to go to a less picturesque destination: Estelí.

Estelí is not a tourist destination; It is a regular working town in central Nicaragua that is famous for growing some of the best tobacco in Central America. At least half of the population of Estelí works in the cigar industry in one way or another. I couldn’t get an accurate count on how many cigar farms or factories there were in the area. I managed to find about 30 online but I was told that there was probably twice as many.
Estelí seemed like a good choice. It’s famous for producing something that I love and, aside from that, it doesn’t really have any other sights or attractions that would distract me from my work. (There are some nearby hikes, but that’s it.)

Arrival in Nicaragua
I flew into Managua and then had to make my way to Estelí. Managua is the closest airport to Estelí and the only way there is by vehicle. There are buses, but they’re slow. I was arriving in Estelí from Vancouver via Mexico City, where I had spent the night, so by the time I would arrive in Nicaragua it would be Saturday afternoon and I wanted to arrive in Estelí before it got dark. So I arranged for a car.
I found a driver online – Mr. Ow of Mr Ow Nica Travel – who offers driving services around the country and asked him if he would make this drive for me. He said he would. I wholly recommend him he was an excellent driver and very professional. It was also nice to make the drive from Managua to Estelí in a car so that I could enjoy the scenery as well as ask Mr. Ow about life in Nicaragua. It wasn’t a super picturesque drive, but it was nice to see some fields of green and donkeys pulling carts.
Growing up, the only time I heard anything about Nicaragua was on the news, and it was always violence and political upheaval, and American-born news reporters with no Spanish accent suddenly pronouncing the name Nicaragua as though they were raised in the heart of Managua. (“Nee-Ka-rrrá-Gua”)
While it’s a bit of a stereotype from Nicaragua it’s also true that it was violent and had political upheaval and lots of American political meddling. The country was under a series of dictatorships and revolutions from the late 1930s until the 90s (Somoza, Sandinistas, Contras), with a war and a devastating earthquake on top of it all. In the 1990s, when it started to re-establish itself as a stable state, it was decimated by terrible hurricanes. It’s only really since about the mid 2000s that it’s got on its feet. Or did it?
While there isn’t any active war, Nicaragua struggles with democracy and dictatorships to this day. Political participation is limited, and the current president has been in power for 23 years across two different periods. During his second period, he removed term limits from the constitution and recently made his wife vice president. When I am visiting countries with tricky governments, I try not to ask people too much about the local politics for fear that they or I get in trouble. To the extent that locals talked about politics with me on this trip they didn’t seem happy with the system and spoke about it in hushed tones.
Nicaragua is one of the safer countries in Central America, but it’s still not considered safe. I felt completely safe the entire time that I was there, but I don’t know if that’s a universal experience.

Estelí
We got to Estelí, it also wasn’t that picturesque, but it would be my home for the next week.


Estelí has a population of approximately 120,000. I find that shocking because it felt like a small town, but I gather that I was staying in the centre and that there is more of the city perhaps spread out. The area that I stayed in felt old-ish. There were some cobblestone-type streets and single-story colonial buildings painted in bright colours and at least one square with an old churches.





It looks lovely right? And it was pretty. Not as pretty as Antigua or Granada, but it did have many of the elements of an attractive Central American colonial town. What it didn’t have was things catering to tourists. On one hand this was great; I felt like Estelí was a completely authentic experience. On the other hand, it wasn’t an easy place to spend a week in. Very few people spoke English, so I had to rely on my rudimentary Spanish. Finding vegetarian food was almost impossible. Most nights I would ask people to make me a bean and vegetable burrito. And one night I just had a virgin piña colada and a cigar for dinner. There wasn’t a plethora of cute little cafes with free Wi-Fi like you would have in a more touristy place like Antigua, but there were some. There was one very picturesque little cafe (Coffee Lovers Estelí) that did have free Wi-Fi and wasn’t too far from my hotel and there was a place selling smoothies and there were and there were one or two patios to sit on.


Sometimes when I drive through countries from one destination to another I will pass by a town or small city of no particular note and I’ll wonder what life is like in a place like that; just a regular town with no real attractions. Estelí was that experience. People got up and they went to work and they hung out in the park in the evening when it was hot and then they went home. Men walked around wearing cowboy hats and cowboy boots and jeans and nobody seemed particularly interested in displaying the sights or history of their town. Every morning, a siren went off at about 5:00 AM signalling to people that it is time to start work. I used this as my signal that I should do likewise.
I stayed the Hotel Los Arcos, which is probably the nicest hotel in the centre of the city and I booked myself into the biggest room. I figured, since I’m going to be there doing work, I may as well have some space. It wasn’t ideal for work, lacking any sort of a desk or table. I spent most of my working days sitting on a wooden bench working at a coffee table in the common areas, smoking cigars. That was great, cigar-wise. The place was very cigar friendly. And while the staff didn’t speak a word of English, they were very kind and we exchanged small conversations.



I did get violently ill for about out two days during my time in Estelí following an attempt to eat a salad ordered from a takeout window at a taco shop. I think that was a mistake. And that put a bit of a damper on things, but I was still able to tend to my work and enjoy my cigars.
And the cigar is really where the highlight of Estelí. I could smoke anywhere, which was a treat, but more importantly I had arranged to visit some farms and factories while I was there. It is possible to arrange for a tour in some cases to visit certain farms and factories there, but they generally don’t do them for individuals. Fortunately, my law firm is one of the sponsors of the Caribbean Cigar Celebration, an annual cigar event in Vancouver, and I used that as my way two reach out to these places. Only three factories got back to me, but that was enough. While I was there, I visited Las Villas, Rocky Patel, and Plasencia. I know that if you don’t know anything about cigars these names won’t mean anything to you, and that’s okay. I will write separate posts about these visits so they’re easy for people to skip if they’re not interested. But for me it was thrilling and one of the more unique trips that I’ve had.



My days in Estelí, apart from visiting farms and factories, were spent with a morning stroll, an eight or so hours of work, and an evening out for dinner, another walk, and a cigar, seeing who I could meet and what I could see along the way. Not exciting, but pleasant.



Would I recommend that people go to Estelí? Not unless you are a huge cigar fan and very excited to learn more about the process of growing cultivating and rolling cigars. Otherwise carry on to Granada or one of the other more touristy regions of Nicaragua.

Moving On
I did go to Grenada on my last weekend, and it was excellent and provided me with all the touristy comforts that Estelí lacked, but the highlight was visiting those tobacco farms and cigar factories, which reaffirmed and revitalized my passion for cigars.
Choose your own adventure! Want to Read about my visits to Las Villas, Rocky Patel, and Plasencia? Click your choice. Want to jump ahead to picturesque Granada? Click here.



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