But that's me.
Did you ask at all with air-only charters? From NYC there are a lot of them, Apple Vacations, etc. If you can go for one week you may save a lot.
I guess you should enroll in Netsavers (set up an AA.com account, then configure it to make pairs of flights from NYC - JFK etc., to SDQ, PUJ, POP and STI) and each time you go to the site it will show you any deals waiting). Then just be prepared to go quick.
The simple truth is that all the airlines have prices around $440-$450 right now including CO (so 777-200: zip it) and US Air. And you either pay or don't go. If you check Expedia flights 4/25 and 5/25 and 6/25 are all at least $440.
So.without Netsavers your $350 embargo keeps you away for the next 3 or 4 months, pity.