Travel Tools - How to find cheap destinations by date?

Good morning!

Please accept my apologies if this is posted in the wrong place or otherwise doesn't make sense.

Essentially, I am trying to find a travel site/tool that will allow me to put in travel dates without entering a destination in order to get the cheapest destinations for those dates.

For example, I am looking to take the family to the Caribbean for Columbus Day weekend or even Thanksgiving. But I don't want to research each and every possible location in the Caribbean. Instead, at a regional scale that tells me, possibly map-based, where the best deals are to be had for the dates I entered.

Any ideas will be greatly appreciated.

Thank you,

Nico

http://www.kayak.com/explore/

Perfect!

Thanks very much, Spark!

Nico

Happy to help.

Skyscanner, while not always particularly accurate, allows you to search from either an airport or a whole country to "everywhere" on a specific date or even across a whole month. It's useful for getting an idea as to what's out there.