So, if I were to move to some random island...my top picks would be:
1) Cost Rica- because its beautiful, I found relatively cheap monthly rentals, and its easy to get a visa to work there for 90 days at a time (thats probably the biggest reason- most of these choices are based on price and ease of working there). Also, they have reasonable flights...like $2700 RT including taxes for all 4 of us.
2) The US Virgin islands- the main perk here is that its owned by the US, and since my hubby is american...we could move over there and work right away. Another plus is that many of the island, if not all, are English speaking. My worry about other islands is that we wouldn't get a job unless we were bilingual. I've looked into St. Croix and St. Eustatius within these islands, and they both look amazing. The flights are pretty good here too, and rentals would be affordable. I'm just not sure how easy jobs would be to come by on this island, or any.
3) Puerto Rico- Same as the last one, this is owned by the US....so ease of working there would be high. This one I don't feel is as appealing as the other 2, and I'm not even sure why....I guess just what I've read online.
If we did something like this, it would be awesome to stop somewhere beautiful on the way too. This is what I've found: THIS deal through aircanadavactions.com makes the flights for 4 TOTAL $740 RT....aMaZiNg!! (June 18th-25th and only if the kids are under 12 though, but works well for us!). If we went here I would stay at THIS resort. Partially because it looks SO awesome....but also it is inexpensive. Everything would be included, entertainment, water sports and food. The first 2 kids are free to stay, eat and play....which is again fantastic for us....and if you book it online through that site, you get a free room upgrade. That all-inclusive resort would be a total of $924 for the week (6 nights, 7 days).
....which would be a grand total of ......$1664 for an all-inclusive vacation for a family of 4!!! Awesome, huh.
I would be ALL for going, if it weren't for the current exchange student that we have right now...she won't be leaving us until June 25th....so here is to hoping that another deal like this pops up later on in the summer months! :)