Nantucket's famous Christmas Stroll is always the first week of December, and the co-owners of Mimi's Place want to do something extra special for the restaurant this year. It will be Emma and Paul's first Christmas together as a couple and Mandy's first holiday as a newly 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. Gina Caruso, the awesome bar manager, is spending her first winter on Nantucket after having lived in Boston for years. She's confused when someone she had a major crush on back in Boston moves to Nantucket, while Jared Hawthorne, the new sous chef at Mimi's Place, makes it his mission to introduce Gina to all of Nantucket's holiday festivities.

Mandy, Emma and Jill O'Toole are as close as three sisters who live hundreds of miles apart can be. They grew up together on Nantucket but have scattered around the country. When their beloved grandmother passes peacefully in her sleep a week before her 99th birthday, she leaves them quite a surprise. In addition to her Nantucket home, they learn that they've inherited Mimi's Place, one of Nantucket's most popular year-round restaurants. They had no idea that she was the silent owner of a restaurant, and no idea how they're going to handle this kind of inheritance. There is, of course, a catch. She left the restaurant equally to Mandy, Emma and Jill --- and also to Paul, the executive chef for the past 15 years. And before they can sell, all three women need to work at the restaurant for a period of one year.