During hurricane season each year I have to "take cover" somewhere for a few months. I don't want to find myself with my family, in an island anchorage somewhere with no protection when a big hurricane starts to brew in the Atlantic. This year we decided to hunker down in Puerto Rico. It might seem like an odd choice, based on how battered Puerto Rico was in 2017, but that year was a bit of an anomoly. While Puerto Rico is well known for being in the path of hurricanes, it doesn't regularly get hammered by big ones like it did that year. And the layout of the island does provide a couple of pretty decent options for protection from the smaller hurricanes.
Our plan had been to hide out on the south side of the island, but we decided to spend the first month (July) in San Juan, on the north. Once there we could never bring ourselves to leave.
Marinas aren't cheap here, but they aren't outrageous like they are in much of the Caribbean. We pay about $800/mo to stay at Club Nautico, a mile down the road from the heart of Old San Juan, and just across a bridge from the popular Condado neighborhood. We're walking distance to a nice grocery store, as well as a bunch of restaurants (at least when COVID isn't closing everything down).
Internet is very much like in the U.S. (meaning fairly mediocre, but with decent coverage). When we first got to Puerto Rico I went to the nearby T-Mobile store and bought two unlimited data SIMS (because nothing is truly unlimited) for $65/mo total. I also have a Google Fi account that goes with me everywhere (again, unlimited, but throttled terribly at 22gb). So in total I've got about 70gb of paid 4G data, plus wifi wherever I can grab it. All of this also worked seamlessly when I popped over to the U.S. Virgin Islands for a month.
The main reason we stayed in San Juan is because there is so much to do. Unfortunately, the coronavirus put a halt to just about everything. Museums closed. Parks closed. Beaches closed. Eventually, though, a few things would begin to open up. We were able to sign our kids up for sailing lessons where they had an absolutely fantastic time learning to sail dinghies from an Olympian alongside a dozen other kids, some of whom they became fast friends with.
Working on a boat can be a bit confining at times, especially when you want to do some video recording. I did a quick google of co-work spaces in San Juan and found a ton to choose from. I settled on a nice building just a five minute walk from the boat. If all you need is an open co-work office space it's incredibly inexpensive at about $5/day. I needed my own office so it was a bit more expensive at $750/mo, but the quiet and the blazing fast internet was well worth it. It wasn't the prettiest office, just a desk and a chair, but it was everything I needed for a few weeks.
During hurricane season we always like to get off the boat and live somewhere else for a month or two. This year we moved just up the road to a condo in Old San Juan. There are a ton of places for rent on AirBnB in every price range imaginable, so I won't bother delving into that. I will say that Old San Juan is a beautiful town and a great place to spend some time exploring. Our visit was during COVID so there were virtually no tourists, which was a bit of a welcome relief, to be honest. During a normal season there would be multiple cruise ships docked in town and 2-5,000 tourists wandering the streets each day. Instead we had the town to ourselves. Just us and the locals with our masks and our social distancing. It was a pleasant summer. And best of all, the hurricanes avoided us, despite it being the busiest Atlantic hurricane season on record.
All in all I highly recommend Puerto Rico. We've always had a nice time here, and this year was no different. For a world-wandering trader it's great. It's not the cheapest place—not a Mexico or Guatemala—but it's reasonable. Everything you need is available easily, and if it isn't you can always order it from Amazon. Yep, Amazon delivers. Good groceries, great food, nice marinas, beautiful beaches, surf, history, culture, and everything else you could ask for is right here in this compact little island.