The Road Less Traveled: Porto, Portugal- October

At the mouth of the Rio Duoro, this hilly city is both modern and decaying; a brand-spanking new metro system travels right past crumbling townhouses that haven't been renovated since they were built hundreds of years ago. But it still holds a certain amount of charm, even for being the second largest city in Portugal (behind, you guessed it, Lisbon). There are medieval and windy alleyways, never-ending staircases, baroque churches, cute plazas and some amazing views. Porto's historic center is a Unesco World Heritage zone that you could spend days getting lost in. Cross the famed Dona Maria Bridge, built by none other than Gustave Eiffel, and you enter the world of port wine (where it was originated and the only place it is produced). Some wine is still brought by wooden barrel on adorable boats into the city- see pictures below.

Scattered across the hillside are various port houses offering tours and tastings, with restaurants and bars lining the riverwalk. Oporto, as it's referred to across Europe, is the birthplace of Prince Henry the Navigator and, some people say, the birthplace of Harry Potter (author J. K. Rowling was living in Porto as an English teacher when she started writing her first book). A visit in spring or summer would be much more lively than fall but it was a weekend well spent (and so close I just might have to go back again soon!)