A week out from our month-long trip, the question we've gotten most so far is "Why Guatemala?" There are many reasons we chose to visit Antigua, Guatemala after seriously looking at several other places that fit our criteria (Panama, Costa Rica, Nicaragua, Columbia, Puerto Rico). Short list of most important factors: time zone/"workability", language, "walkability", activities, weather, and cost.
Longer answer:
Time Zone/Work
Bill will be working remotely much of the time we're there. His supervisor doesn't care where he's physically working since their team is fully remote, but joining meetings would be difficult if we were outside of the Americas. We focused our search on Central and South America and referenced "best places for digital nomads" lists for ideas. Guatemala uses the equivalent of US Mountain Time, and is supposed to have reasonably reliable and fast internet.
Language
We previously decided that we should learn Spanish in order to make it easier to visit the many Spanish-speaking countries. I'm currently taking Spanish 3 at our local community college, and both Bill and I are also learning with Duolingo. When we visited Costa Rica, there was basically no need to speak Spanish (in touristy-areas, I assume that's not true everywhere), but I'm actually hoping there's less English spoken in Antigua to force us to use Spanish. Necesito practicar mucho.
"Walkability"
We walk for exercise most days, so wanted to find a place where we could safely and easily do so. We also didn't want to have to rent a car for a full month. Antigua has a small enough downtown that we can walk everywhere from our AirBnB. In addition to local buses, they have Uber (easy) and tuktuks to get around cheaply.
Activities
The girls and I want to explore while Bill's working, so again needed to be somewhere that's both easy to get around and also has interesting places nearby. It looks like there's a lot to do in and around Antigua, plus our AirBnB has a shared pool and play area with a trampoline. Outside of all the official touristy options, the girls are planning an exhaustive comparison of helado at every ice cream shop in Antigua. :)
Weather
North Carolina is hot in the summer and I love to escape that when possible. Basically every city we were considering had more temperate weather in the summer than NC, which surprised me since they're all so close to the equator. Antigua is 5000 ft above sea level and generally stays between 60-75 degrees year round. Looking at the weather a week out (highs around 70), I'm hoping it feels warm enough for us to use the pool!
Cost
There are many cities that met the above criteria, but looking for cheap flights was ultimately what led us to Guatemala. Flights are often the most expensive part of a big family trip, so I usually like to start there vs. picking a firm location first. I hadn't considered Guatemala until Guatemala City popped up in my broad Google Flight search as a reasonably priced option. If you haven't used it, check out the Google Flight "Explore destinations" option, which lets you drag around a world map to see the cheapest flights to airports everywhere, filtering by price (etc.) if you'd like. When you'd be happy in a bunch of different countries, might as well pick one that saves a bunch on flights! More $ for fun during the trip. Google's "Date grid" and "Price graph" options helped us find the cheapest days to fly - we could be flexible to help keep the cost down since we didn't have specific date constraints like we would with spring break or Xmas vacation.
I'll do a full post after the trip on final costs, but flights were <$500/person. After using credit card rewards to cover the bulk of that, we spent ~$340 total for 4 flights. AirBnB options in Antigua are comparable or slightly cheaper than the other cities on our list too, and our townhouse - like most AirBnBs - offered a large discount for a month-long stay.
Bonus Reasons
So many other reasons, including that Antigua is adorable and is surrounded by 4 volcanos. How cool will it be to see a volcano from the swimming pool, or roast a marshmallow on an actual volcano?! Stay tuned!