In the year before the 1904 St Louis World’s Fair, the four Smith daughters learn lessons of life and love, even as they prepare for a reluctant move to New York.

As Christmas approaches, Paula, a St. Louis antique appraiser, reluctantly accepts a marriage proposal from her boyfriend, Daniel, a career-focused attorney. When her Aunt Jane senses she has mixed emotions over the engagement, she invites Paula to her Nantucket home. Upon her arrival, Paula plans a trip to the nearby island of Martha’s Vineyard where she meets a charming inn owner.