If you can modify your plans a little, here's a way to maybe start in that direction. IF you can start working four ten hour days and give yourself three day weekends, you gain some room to move from place to place during those three days. If you start your cruising life in the Florida keys
, you can use those weekend windows to move from spot to spot that has internet. Don't even plan on using marinas
at all for internet. Buy up all the Mobile hotspots you need for where you're cruising. A combination of Verizon and AT&T will cover you until you get into the Bahamas
. Then buy a BTC sim card and mobile hotspot. You can spend a week in a place, while working and planning your next stop. Then on a three day weekend when you have the weather
, you dash off to the next spot and set up camp there. You can do quite a bit of sailing this way, between Florida
, the Bahamas, the Caribbean
, and Central America
. Just takes a willingness to compromise and to plan ahead.
As for the idea of getting reliable internet at sea or in very remote places, you've already heard the bad news on that. The people who do that run heavily funded research
ships, basically, and need internet. And even they don't work with VPN or remote desk top type setups.
We keep thinking that affordable world wide internet to moving platforms will happen in our lifetime, but meantime, we've managed to make a few trips under those conditions I described. We took 40 days to get our old boat from Jacksonville
to the TCI, and my wife was able to work her software
development consultancy for most of the way with the combination of wifi mobile hotspots. We traveled on weekends.