Charlie (McShane) is an amorous English tour guide who takes groups of Americans on whirlwind 18-day sightseeing tours of Europe. Among his various clients on his latest trip are Samantha (Pleshette) with whom he wants to have an affair, a man who desires a pair of custom-made Italian shoes from a certain cobbler in Rome, another man (Baron) who is secretly being set up for a surprise marriage with his Italian cousin, and an Army veteran who is reliving his World War II experiences.