Naples at $435 RT

There's no better starting point in Italy than Naples! Aside from literally inventing one of the most popular foods of all time, it's also got a primo location.

After all, how many cities have legendary volcanic ruins as a neighbor?

Hop down a little further, and you're along the Amalfi Coast — two of the most enviable words in the travel lexicon. It's a bit of a different experience in February, when most of the crowds have dissipated. It's less "sun-soaked Instagram photos" and more "hauntingly beautiful coastline rising through the mist." 

And lastly, we hear there's this REALLY old city about 70 minutes away by train. Some might even say it's... eternal :-)