GPS and electronic charts?
James, your inclination to rely solely on paper charts and a GPS is not a bad idea. Somehow, we''ve come to adopt the notion that without seeing the chart electronically, our (GPS-based) navigation is unsafe; that''s hooey.
The areas you are planning to visit have not been of strategic interest to the First World countries for many decades now (except the local waters around Cuba''s SE coast where Guantanamo Bay is located) and so you will not find the BA or NIMA charts to be especially detailed nor regularly updated. (This means by definition that any vector or raster chart based off those data sources is also deficient). The exception to that statement is the beautifully detailed Cuban charts (now sold under license by Blue Water Books), which were originally developed by the Russians and now maintained by the Cubans. These are available in paper and electronic formats, and you''ll need to sort out how to match your budget with their cost and your cruising plans - especially since a visit to Jamaica might also include visits to a number of Cuban pors and coastal areas on both coasts (all heavily controlled, by the way). Keep in mind due to their limited resources, even the Cuban charts will vary from reality due to storm damage. (We had planned a run along their S coast in 2002, departing from Port Antonio, but gave up after getting reports from boats leaving Cuba that couldn''t find channels, buoys etc. where their Cuban charts said they existed; this was right after a major storm passed thru).
You might consider another alternative re: equipping your boat: a Yeoman Navigator Pro, which is a graphics tablet the likely size of your chart table, and plot off of it using paper charts. The Yeoman takes a GPS input, has a mouse which is used on top of each paper chart, and one can create and upload (to one''s GPS) waypoints when plotting routes, instantly see via the mouse the boat''s location on the paper chart, it will work on ANY chart, and it allows you to enjoy GPS accuracy on paper charts with no manual plotting...BUT only to the degree the paper charts permit this.
FWIW the rest of that part of the Caribbean (Haiti, Jamaica, Caymans, Honduran Bay Is., Belize and Mexico) do not IMO require electronic charting; it''s just a convenience. With the exception of the changes in the large, often remote Cuban waters due to storms which have not been recharted, things are pretty straightforward everywhere and the charts + select guides (e.g. Rauscher''s guide to the W Caribbean and John Lethbridge''s dated but still very useful guide to Jamaica) provide more than adequate pilotage info.