Best SIM or data plan for the Caribbean season?

Crossing in a few weeks and I don't want to spend the season on marina wifi. Is it worth getting a local SIM per island, or is there one regional plan that covers most of it? Roaming from a European contract is going to bankrupt me.

Regional plan. Buying a SIM per island is a false economy when you're moving every ten days — you end up with six SIMs and credit stranded on all of them. Get whichever regional carrier your crew are already on, because then you can hotspot off each other when one has coverage and the other doesn't.

Also check whether the boat's Starlink has a crew allowance. More and more do now, and it's changed what a season feels like. Ask at interview — it's a fair question.

An eSIM saved me a lot of hassle last season. No swapping physical cards on a tender, and you can keep your home number active for the bank codes.