Two brothers, Joe and Brian Hackett, run a one-plane commuter service from a small Nantucket airport. Along with Joe's on-again/off-again girlfriend, there are more hilarious and eccentric characters who work out of or at the airport.
After selling off the valuables of her Georges,Fay is visited by their ghosts,demanding that she buy back their items. Meanwhile,Joe's Valentine's Day efforts seem paltry to Helen compared to the man intending to propose to his beloved with a banner flying from the Sandpiper plane (problem is she's not his beloved,and she can't even stand him.) and Brian and Casey prepare to go out on a sham date.
The gang accompanies Helen to Boston after she lands a gig with the Boston Symphony Orchestra. Caught up in a heavy storm and their fate uncertain, Helen recounts the bizarre way in which they got to that point.
Joe and Brian are thrilled at the return of Grandpa Hackett, but Helen isn't so sure he is who he claims to be. Meanwhile, Antonio refuses to continue a chain letter, which everyone else gets and passes along, and begins to suffer for it.
Joe and Brian are divided over their new-found inheritance:Joe wants to expand the business,and Brian wants the money to leave Nantucket and the tedium of his job.Joe's agony over the dissolving of the partnership is further complicated when he learns of Helen's earth shaking news:she's been invited to study cello in Vienna with the world's greatest cellist.Joe is prepared to sacrifice Sandpiper to help Helen finally live her dream.But it is Brian who makes the final sacrifice,by postponing his and Casey's move to the Carribean,in order to run Sandpiper for one year while Joe and Helen are away in Vienna.
The sad news of Richard Kingsbury's death in Miami is occasion for celebration at Sandpiper, as Kingbury's oldest daughter hires the Hackett's to bring the body back to Nantucket for the Memorial. But the brother's fly the wrong body back to the island, and it's up to Joe to impersonate the late Kingsbury at the funeral.
With Joe MIA, the burden of running Sandpiper Air falls all on Brian. As he struggles to keep things in the air, he gets a clue to where Joe ran off to.
On their way home from Las Vegas,Joe has a bad case of food poisoning and is soon helpless in the airliner's bathroom.Where he is soon followed by the plains pilots.Leaving the job of hero to be played by Brian who safely lands the plane and becomes an instant celebrity. Joe tries to deal with Brian's newfound celebrity and all the grief he's getting from Helen over his "Men's travel bag",but Brian's celebrity is short lived and he soon is back at Sandpiper asking for his old job back once again.
After Joe and Helen burn down Brian's house,he's expecting a big check,much like the one Joe and Helen got,but the gutting of the old Hackett house is cause for an appearance by an insurance investigator,who has serious doubt about the legitimacy of the two claims in the last year.Until she and Antonio's wild night of passion sparks a blaze at the local hotel and that convinces her the cases are Legit.
To lift Antonio's spirits after he's dumped by the "Big Faced Girl," Joe and Brian set him up with a girl at the Club Car only to discover later that she's a very expensive hooker.
To help pay off 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 Retired Businessman of the Year banquet.
Spurned by Joe (who's too busy with his new wife to spend time with him), Brian turns to food, but ends up trying to deal with his problems at a meeting of the "Eat-A-Holics." Meanwhile, Antonio tries to get used to tight shoes, after he pays $200 for them, and Casey gets hired by the Nantucket Tourism Board.
When digging through the rubble of Helen's home, Brian and casey unearth a suitcase and photgraph that had been the hackett brother's only inheritance from their late father. Brian's attempts to remind Joe of that fail,but Joe later sees a vision of his late father and forgives Brian. Meanwhile,Antonio executes his revenge on Brian and Casey and Helen takes out her anger on Casey's clothes.
Joe and Helen return from their honeymoon in Jamaica to recieve bad news; a night of passion between Brian and Casey in Helen's house results in a devastating fire. That Leaves Brian kicked out of the house and Sandpiper by Joe.
Fay is understanding when Joe tells her he won't be able to give her a raise but when she sees the brothers gloating over a pair of new leather flight jackets, she is outraged and quits.
Joe, Brian, Helen, and Lowell struggle with the return of their 9th grade English teacher on whom the boys had a serious crush. Meanwhile, Roy is dubious about why a "Simon Says" expert wants to marry his mother.
Brian and Casey decide to throw Joe and Helen with a surprise engagement party as a way to apologize for not giving them some much needed time alone.
It's Roy's 12th birthday (he was born on a leap year), and Helen contacts Roy's son R.J. and convinces him to come back to Nantucket for the party. But the initial reconciliation is dashed when R.J. brings his significant other to the party. Meanwhile, Brian helps Antonio out by driving the cab while Antonio waits for his driver's license.
When news arrives that Sandy Cooper is returning to Nantucket, Joe fears her high school obsession with him will return but the others think he's imagining things. Meanwhile, Antonio tries to raise money to send to his family and Roy is worried about a visit from his cranky mother.
Helen dates a guy with an annoying laugh. Antonio has trouble with his jerk neighbor.
Back from vacation, Lowell goes out for a meal of hot wings with Antonio and lands in hot water when he witnesses a mob hit. After he is threatened by the gangster's lawyer, he decides to join the Witness Protection Program and leave Nantucket forever.
Brian makes a video diary of Joe and Helen's relationship for them as a wedding gift.
After having a few drinks, Alex asks Joe to drive her home and when he arrives late the next day everyone assumes that they spent the night together.
Brian falls for "R",after reading her love letters,mistakenly sent to a former occupant of the house. Meanwhile,Joe and Helen ask Antonio to install a new security system in their house.
Helen is in desperate need of Roy's help when she discovers that she and Antonio are still married.
The news that the Hacketts' old house has been condemned due to storm damage has the two brothers reminiscing about their childhoods.
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