Travel Nut here… Mr TTR & I are semi-retired, and able to travel quite a bit.
As a Canadian (I assume based on your Avatar), you’ll find you can get good deals for AIs in Mexico – Cuba – Dominican Republic – and Jamaica
The thing is there are deals because all of these places have issues… be they political, economic or social… so in order to attract the much needed tourist dollars they build AIs and offer good prices.
The truth is in many of these places this isn’t going to be a world like the one you have at home… none of these are 1st World Countries… and at least one is 3rd World.
Safety is also a major factor… so if you are the type who likes to explore, you might want to think twice of going beyond the resort unless it is on a Resort Organized Tour
Not to say that the resorts are nice, cause many of them are… just that they are sort of Disney-like existence, where you are in an isolated world (walled, and often armed guards) seperating you from the rest of the locals.
For me, that isn’t a reality that I want any part of…
AIs elsewhere in the Caribbean are going to be more costly because those Islands don’t require this type of accommodations solely to attract tourists… consequently there is a lot more to choose from on each island (ie Aruba, Barbados, Antigua, Turks & Caicos, The Bahamas etc)
Personally, I prefer to spend my own vacation dollars in places like those… or Florida (the whole state is gorgeous… and a lot less less expensive than the Caribbean… and yet The Keys have pretty much the same vibe)…
Or we go on a cruise…
Mr TTR and I have done several cruises now… and some can be quite similar to the benefits of an AI Holiday (several cruise lines now offer Beverage Packages)… with the BONUS of waking up each day in a new Country / Island to explore. And nothing beats the pampering to be found on a decent cruise ship.
For $ 4000 all in, you could definitely do Florida, the Bahamas, or a Caribbean Cruise. You’d probably need to raise your Budget to go to other Caribbean places because of high cost of airfare.
Hope this helps,