Joe is thrilled to learn that, for a charity auction, a plane ticket he donated to fly to any nearby airport goes for a staggering $10,000. But his mood sours when a misprint on the ticket forces him to fly crabby old Carlton Blanchard on a cross-country trip for a reunion with his brother.

Helen throws a surprise birthday for Nantucket's most unpopular resident, 70-year-old Carlton Blanchard, who threatens to become a permanent household fixture after suffering a fall in her home.

To help pay for his new used cab, Antonio gets a job as a chauffeur for Carlton Blanchard. Things get even worse when Carlton's equally annoying nephew, Lewis, arrives on Nantucket to attend Carlton's banquet.