If the approach of winter has you dreaming of Caribbean island escapes, you might want to consider Barbados. We have found November and December flights on American Airlines between New York City and Bridgetown for as low $398 round-trip.
If that is not enough to convince you, how about some spending money? The Barbados Tourism Authority is offering an "Island Inclusive" package to visitors who book a Barbados hotel through them, with a spending credit of up to $200 per person. This "free money" is actually given in vouchers, which are redeemable at select businesses and restaurants (listed here).
To get the $200, you have to stay at least seven nights (visitors who stay five nights get $150 per person).
So, flying American Airlines from NYC to Bridgetown on November 14th and returning on November 21st would cost you $398 per person. Add seven nights at a three-star hotel (we checked the Time Out hotel) for $469, and that makes the total $1,265 for two people including the flights – or $633 per person. Throw in the $200 per person free spending money and it adds up to an affordable winter vacation.
You might argue there's no such thing as free money, so take note of a few catches before booking: The package must be booked through the Barbados Tourism Authority website, using the the booking code BII2013. The package also must be reserved before September 21st and is only valid for vacations up until December 21st.