Nantucket, Massachusetts
Where to fly: Boston Logan International Airport
As it turns out, Nantucket actually proves to be equally charming during the off-season, when the summertime tourists have vacated and the locals put on a stunning display of holiday cheer throughout the town.
Head to this scenic part of Massachusetts during the first full weekend in December to participate in the Christmas Stroll, where you can simultaneously sip on mulled wine, listen to carolers, and shop for unique Christmas gifts.
After the stroll has commenced, be sure to stop and take in what has made this area so famous during the holiday season—its hundreds of adorned seven-foot-tall Christmas trees that grace nearly every spare corner of the town.
Pro tip: One of the more recent establishments to crop up in this beach side town is the impressively cozy Greydon House, a boutique hotel that’s made perfect for the winter season with snug furniture tucked around every corner—each making for a great reading nook when you find a moment of alone time.
