Annabelle Wilson (Kathie Lee Gifford) is suddenly widowed after a 32-year marriage to her husband, Fred. They have lived on Nantucket the entire time, running their hardware store and going to the movies every week.
While reading his last will and testament she discovers that upon his death he wishes to be cremated and have his ashes put in "a box of chocolates" because 'Forrest Gump' was his favourite movie. This discovery begins a whole new season of her life where she sets out to fulfil her own long, lost dreams. She makes a list of their favourite 20 movies, sells her house and the hardware store, and leaves her life on Nantucket behind forever. She travels to Scotland first, in honour of 'Braveheart', where she meets a crusty Inn owner named Lord Howard Awd (Craig Ferguson).
Annabelle is immediately stunned and seduced by the sheer power and passionate beauty of the Scottish countryside. Her breath is literally taken away by the ancient landscapes draped first in sunlight, then raindrops, then rainbows. She finds herself profoundly aware that this country is going to impact her very soul in ways she could never have imagined. In Lock Lomond, she checks into an inn owned by and operated by a crusty, weathered Scotsman, Lord Howard Awd. Polar opposites, Annabelle and Howard spend one week discovering secrets they've never shared and develop an unlikely friendship. Will it lead to a last chance at love for both of them? There's a complication: Howard is scheduled to be married at the end of the week!