At the wedding of the century, candy store co-owner, Ann Jones declares her intentions to get her well-manicured hands on the town's new doctor, Nate Flynn and never let go. She's never had trouble getting her man, so it's only a matter of time and the right outfit.
Nate, cautious with his heart after being burned, has his intentions set on getting to know Ann's sister and store co-owner, Jo.
It's going to be a busy Christmas season in Pirate's Nest, the quaint New England village with the contrary name. As the last of Thanksgiving dinner is eaten and the Christmas tree is on its way to being decorated, some of the residents are feeling love in the winter air, some are feeling bypassed by love yet again and some are feeling the heat of sibling rivalry.