Nantucket's famous Christmas Stroll is always the first weekend of December and this year sisters Mandy and Emma, and Paul, the executive chef, want to do something extra special for Mimi's Place, the restaurant they co-own. It will be Emma and Paul's first Christmas together as a couple and Mandy's first holiday as a newly single and divorced mother of two. Although Mandy does have a promising new relationship, she wants to take things very slow. Their sister Jill and her new husband, Billy, are planning to spend the whole month of December on Nantucket too, juggling working remotely for the executive search firm they own together in Manhattan and relaxing and spending time with family and helping out at the restaurant too. And Gina, one of their best servers and bartender, is spending her first winter on Nantucket and it's a bit of an adjustment. Winters on Nantucket are so much quieter than the city life she was used to. She's even more confused when someone she had a major crush on back in the city moves to Nantucket. Suddenly her boring winter is starting to look a lot more interesting.