Situated roughly halfway between Athens and Crete, Santorini is the supermodel of the Greek islands. Famous for its whitewashed buildings, winding cobblestone streets, and dazzling panoramas, this Mediterranean oasis will offer plenty of gasp-inducing views of land and sea.
And while most people flock to this isle during the Summer, the Winter months are a great time to visit if you're looking to do more than simply sunbathe, as it is during this time that you can stretch your budget the farthest. Plus, with fewer crowds, you'll be able to soak in a lot more peace and quiet. Although Winter here is quite warm, with just the occasional drops of rain, be sure to bring a light jacket for when the sun goes down.
Average January weather: high of 54 degrees with very few inches of rain