Nantucket's famous Christmas Stroll is always the first week 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 that 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. 

Mandy, Emma, and Jill are as close as three sisters who live hundreds of miles apart can be. They grew up together on Nantucket, but Mandy is the only one that stayed. The girls are stunned when they learn about the restaurant, Mimi's Place, and the condition their grandmother added to the will, leaving the restaurant equally to Mandy, Emma, and Jill - and also to Paul, the chef for the past 12 years, and Emma's first love. 

Jill Conroy is tricked by her sister into becoming the housekeeper and cook for the summer at Seashell Cottage where Greg Campbell and his nephew, Brody, have been hired to do maintenance projects on the house. Annoyed at first, Jill soon realizes how wonderful it is to be away from her home in New York and the memories of her deceased, emotionally abusive husband. Soon the magic of the beach heals Jill enough for her to decide to move to Florida permanently to make a new life for herself.

With her unexpected pregnancy, Carol Ann breaks free from her dismal life with her parents. Left on her own with no support from the father of her child, she decides to start an interior decorating business on the side. She begins by secretly helping Ed Pritchard, her boss at MacTel, decorate his condo for Christmas. One secret Sunday leads to others. Carol Ann and Ed are planning a future together when Ed is diagnosed with a serious illness. He decides it's only fair to break off his engagement to Carol Ann. Devastated, Carol Ann wonders how she can continue. 

Four women, all at different stages of their life, are brought together as they overcome the challenges that life tends to throw in our way - and learn to embrace the surprises, too, as each faces a second chance at happiness.