I tried to do this with a job (remote job, of course) and a family (two kids, 4 and 10, and a dog) and it's possible. I did it for 6 months last year, and three months so far this year. But I'm done, at least for now. It's so much more work than not doing it. Staying home is 100x easier.

There are great things about the cruising life. The fantastic weather, the amazing beaches. You do meet cool people.

There are downsides, too. Some of them are facts of life on a boat. Will the anchor drag? Will we break something in heavy weather? Others of them are facts of life when dealing with island governments. Checking in or out takes all day (especially with the dog and covid). Nobody actually knows what paperwork you need. You get conflicting info from different people.

Some of them are island infrastructure and lifestyle things. Trying to work remotely from a boat? I hope you have good cell service. Sometimes you do. Sometimes you don't. You can try moving or waiting. Maybe it'll get better, maybe it won't. This is also true for kids doing online school. Does it work today? It might! Or maybe you need someone to do some welding to fix a problem with your solar arch. How many days in a row can someone tell you they'll do it "tomorrow"? I'll give you a hint, it's a lot!

Some of it is that most of the Caribbean is not really how you think it is if you haven't spent time there. Lots of islands barely have one decent anchorage. Want an anchorage that's actually protected and also has a decent beach and doesn't have loud music blasting from said beach all evening? There are literally several of these. They're full of boats. Also the ones with parties are full of boats, if that's your thing.

All of the sailing is exposed. This is probably not true in the Bahamas, but it's pretty much true of the entire Lesser Antilles. This doesn't have to be a negative, really, but there's almost no "inshore" sailing in this part of the world. When every trip between anchorages is on the open Atlantic, and your bringing your wife and small kids, all your trips are very carefully arranged around sea state and weather conditions, and the burden as the captain of the boat to keep everyone comfortable is high.

And on top of all this, if you're working, you're spending 30-40 hours a week sitting inside the boat, in a small space with none of the comforts of home. Roughing it all the time while still trying to be productive and having nowhere to go to get away from small children who are just noise machines gets old.

I've realized I like sailing more than I like living on a boat. I also like warm weather and nice beaches, but you only get so much of that while working anyway. I'm actually excited to go home and get the little boat ready for the race season. But I never have to sleep on it or do work from it.

So, I'm ready for a break. I'm not sure when I'll come back. Maybe next year? Maybe after my kids have grown? I don't know. Right now, the whole process is exhausting trying to do everything at once.