5. San Juan, Puerto Rico
The holidays are a jam-packed and exciting time to be in Puerto Rico, and you don’t even need a passport to travel there from the U.S. The entire month of December boasts activities from open-air food festivals to holiday bazaars and parades, and January is the month of the San Sebastián Street Festival. Regardless of what month you visit, there’s nothing like taking a stroll along the colorful streets of Old San Juan and enjoying the sunny beaches to take the winter blues away.