When aspiring magazine writer Sophia Marcus and would-be restaurateur Victor fly from New York to Italy for a vacation, the stage seems set for some much-needed romance in their relationship - especially since their destination is the city of Verona, home of the star-crossed lover Juliet Capulet of Romeo & Juliet fame. But Victor is far more interested in finding suppliers for his future restaurant than in wooing Sophia, who ends up getting a vicarious romantic fix from an unlikely source; she joins a group of volunteers who respond to letters that pour into Verona from around the world - letters to Juliet seeking advice about love. One such letter that Sophia responds to dates back to 1951 and came from one Claire Smith, an Englishwoman who fell in love with a young Italian man in her youth but let the opportunity slip away. To Sophia's surprise, her letter inspires Claire, now a grandmother, to travel to Verona in search of her long-lost love - accompanied by her grandson Charlie. With Victor wrapped up in his culinary quest, Sophia, Charlie and Claire scour the beautiful Italian countryside in search of Claire's long-lost love. In the process, romance blossoms in unexpected ways, eventually facing Sophia with the very advice she wrote in her letter to Claire. Will she find the courage to seize love or - like Claire - spend a lifetime regretting the road not taken?