Brooke, a young marketing executive, goes back to her hometown excited to relive her Christmas memories, while helping a struggling family-owned winery. Her marketing assignment involves an unlikely partnership with Tyler, the charismatic, yet stubborn owner of the winery. Brooke quickly learns that the town’s Christmas spirit has disappeared due to a wine conglomerate buying out all of the local wineries. Determined to bring Christmas back to the town, Brooke and Tyler work together and discover they share more than a love for wine.

Dodie is a hopeless romantic just like the pieces in her vintage antique shop. When Dodie finds a hidden box full of romantic trinkets, she makes it her mission to deliver it to its rightful owner. Following the address, she manages to persuade the handsome but reluctant new tenant, Edward, to help her with her search.

When Lacey takes a rare break from work for her friend Ava's Christmas Eve wedding, she reconnects with her former flame, Ean. The two decorate the cottage where the newlyweds will spend their honeymoon – a cottage said to bring true love to anyone who stays there – and feel their chemistry return.

A campy look at the making of the 1964-67 TV series, as told by stars Bob Denver, Dawn Wells and Russell Johnson, as well as in flashbacks (actors play the castaways). Bob/Gilligan: Jon Wellner. Dawn/Mary Ann: Samantha Harris. Tina/Ginger: Kristen Dalton. Alan/Skipper: Eric Allan Kramer. Russell/Professor: Michael Wiseman. Jim/Mr. Howell: Steve Vinovich. Natalie/Mrs. Howell: E.J. Peaker. Sherwood Schwartz: Aaron Lustig.