33. Porto, Portugal
Why you should go: Located along the Douro river, Porto’s climate is practically Mediterranean, making it a great spot for winter break (if it’s sunny, you can still enjoy the Ribeira, the lively riverside promenade). The second-largest city in Portugal, Porto is famous for its medieval architecture, ornate tilework, and, of course, the port caves that give it its name.
Why it’s a steal: The average flight to Porto costs $681 between December and March, while hotel rooms are 10 percent cheaper than during the fall at $113 per night.
Where to stay: Porto’s Torel Avantgarde hotel opened in fall 2017, and it’s as colorful as the city itself (which you can take in from the rooftop terrace and pool). Each room is inspired by a different cultural figure (think: Frida Kahlo and Andy Warhol). Rates start at $130.
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