Why island hopping changes the answer
A local SIM bought in Barbados does not help you in Saint Lucia. Each island is a new purchase or a new roaming charge, and the hops are short enough that people make several of them in a week.
Some regional operators do cover multiple islands under one brand, which softens this. It is worth checking whether the islands on your itinerary happen to share one.
Cruise passengers need to know one thing
At sea, your phone connects to the ship satellite network, not to any island network. No travel eSIM covers that, and the rates on a maritime network are the ones people tell horror stories about.
The practical answer is to keep data switched off at sea and use your plan in port. Any product that implies otherwise is not describing how maritime roaming works.
Coverage in the places you will actually be
Resort areas, cruise ports and the main towns are generally well covered on the larger islands. Interiors, smaller cays and the quieter eastern islands are more variable.
Weather matters here in a way it does not elsewhere. Network infrastructure in the hurricane belt takes damage, and recovery after a storm takes time.
How to decide
One island, one week: buy for that island, or check whether your own plan already includes it, because some North American contracts do.
More than one island, or a sailing itinerary: a regional plan is the only version of this that does not involve buying something new every few days.
Where are you going?
DestinationsCommon questions
Does one plan work across all the islands?
A regional plan is designed to. A local SIM from one island will not, because each island is a separate market.
Will my eSIM work on a cruise ship?
No. At sea you are on the ship satellite network, which is separate from every island network and charged separately. Use data in port.
Do American plans cover the Caribbean?
Some do for specific islands, particularly Puerto Rico and the United States Virgin Islands. Check your own tariff rather than assuming.
Is coverage affected by storms?
Yes. This is the hurricane belt and network damage after a storm is real. It is a planning consideration rather than a product feature.