San Jose del Sur
Solo Remote Work Adventure
There have been a few occasions where Stephanie and I have not traveled together, outside of work obligations. She’s taken trips to Paris and Italy with one of our daughters and her mom, and most recently, a cruise through the Norwegian Fjords with her mother. I, myself, have not. No particular reason, other than I do remember the feelings I had before we met, traveling the world without my previous partner, and then as a divorced father of 4. Not the most fun.
But when Stephanie discussed taking her mom with her on the cruise, I looked at my calendar and saw that my work obligations didn’t require any travel for a 3 day period, which meant that I didn’t have any constraints so long as I had a good internet connection and a timezone that wouldn’t break up my sleep pattern.
I decided to look for somewhere that was within the central US timezone, reasonable airfares (or awards miles), and a flight table that wouldn’t disrupt my ability to not miss a beat of my 8-5 work day with travel.
The opportunity to scout out a future adventure is what I sought. There are several countries in Central and South America we haven’t visited yet, so that I set my sights on that area. I’d been to Costa Rica (interestingly, I was visiting San Jose when Stephanie and I first began conversing), so I took that off the list. Same with cities in countries we’d already visited together.
So, I decided to take a different approach and let airline miles make the determination. One of the credit card hacks we use is the fact that our American Express platinum cards (both personal and business) provide a $200 travel credit each year. Simply, you register the airline you want to use it towards, and it will credit certain fees up to that limit. But, with AA Platinum status and credit cards for the other US airlines, we don’t really find a need for checked baggage fee waivers, etc. The trick is that (and I hope I’m not jinxing this) United Airlines allows you to fund your United Airlines Travel Bank, and it codes in such a way that American Express credits it back to you. So, I did have $400 available with United Airlines.
With that knowledge, I began researching where I could go for ~$400 round trip between Chicago and Managua, and remembered that I had researched the beach town of San Juan del Sur in Nicaragua last year. So, I went back and looked to see what Airbnb prices were for a 4d/3nt stay, and found that I could get a very nice loft overlooking the beach for $358.
Bookmarking that I watched prices to find the optimal time to purchase. I settled on April but, because I don’t have any status with United, spent $85 out-of-pocket to upgrade to premium seating round trip. I used points I had with Enterprise to cover the cost of the rental car, as the town is a few hours drive from Managua.
Accommodations
The Santa Cruz Luxury Loft is the perfect place for a single person or couple who wants a relaxing stay in San Juan del Sur just a short drive from the town central. A short drive up a hill, it opens to a well-appointed first floor with a bathroom (complete with urinal!) futon sofa, and modern kitchen. But the showcase is the plunge pool, with a commanding view of the beach and water just below. Upstairs is a king size bed and a full bathroom. I appreciated that they had a split on this floor, which I really only needed during the evenings. Nary a mosquito to worry about too.
Exploring San Juan del Sur
My day would start with going into the town for breakfast, which was both convenient and inexpensive. It was easy to drive the 5 minutes down the hill (the road down is undeveloped, making walking a bit hazardous and messy), parking pretty much anywhere you want, then you have your choice of restaurants, cafes and bars. A few of the days would start with “office work” activities - emails, etc., for which I would just walk down to the internet cafe. Otherwise, I’d go back to the loft and work from my portable office replete with a 2nd monitor. Being able to turn around and look out to the pool awaiting me at 5 o’clock was my daily inspiration.
In the evening, I would pick one of the restaurants on the beach and just hang out, beer in hand, watching the sunset and enjoying the laid back lifestyle Stephanie and I are working so hard to experience full-time. Below are the places I enjoyed.
I looked forward to having lunch here, and it did not disappoint. The special of the day was freshly caught tuna and it looked as good as it tasted.
The power was out in the town for a few hours, but I was able to enjoy a nice coffee and lemonade here.
A kosher restaurant, they had the best avocado toast, with a side of warm and friendly staff. I really enjoyed the early morning, sitting by the open window and watching the morning start.
An internet cafe with a wide assortment of smoothies, I didn’t spend as much time here as I could have, but will make up for it on my next visit.
My last evening was capped off with another delicious seafood meal of lobster in garlic sauce at Bar Y Restaurante Brisas Marina
The next day, I completed my work day and drove back to the airport for my flight home, got a good night’s sleep, then headed back to the airport to pick up Stephanie and her mom.
This was the furthest apart we’d been from each other (except maybe a work trip to India last year). It was enjoyable to get away for a few days, but each FaceTime was regaling each other with the experiences we were having while also missing the shared time.
Still, I was so proud of how Stephanie navigated an international trip as host, and hope she shares the story of that adventure here too.
If you have any questions about San Jose del Sur, please leave me in the comments or reach out to us on the socials. It is an undiscovered bit of paradise, and a place I’m looking forward to returning to together.
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