You’ll love BVI (via video and future in-real-life). Thanks for watching!
Customs and Immigration is a (fun) challenge and varies a bit by country. But generally, yes, at each country you’ll need to file some paperwork (manifest, sometimes online in advance, sometimes once you arrive). You can use the FBOs (for $$$) and/or a “handler”… or you can roll your own. In increasing difficulty/expense of the countries we stopped in… Bahamas, Dominica, Nevis, BVI, Dominican Republic, Turks&Caicos. There’s good info on all this in the AOPA Bahamas and Caribbean guides (worth the money).
So yes the flying is relatively easy, the paperwork a bit of a challenge… but it’s very very doable. See the AOPA guides and as you get closer, toss me some questions. Also join the Facebook Bahamas and Caribbean pilot groups.
Approach plates… you’ll need a Jeppesen subscription, which is a plugin for ForeFlight.
Panel avionics… you’ll also need to make sure your panel avionics, e.g. if I remember correctly, the Garmin “Americas” plan covers the Caribbean.
I’m enjoying the questions…so don’t be shy. I’d suggest the AOPA guides are a good thing you should be starting to study. Also make sure you look at all the “tabs” at the bottom of my Caribbean Planning Spreadsheet: http://bit.ly/wam-carib-spreadsheet
What’s your desired timing of the adventure?
All the best,