Helen is bitten by the flying bug after Brian lets her take the plane's controls for a few minutes. She decides to take flying lessons from Joe but his classes are too long and boring so Brian offers to take her up again. They experience some turbulence and Helen finds herself at the controls but never learned how to land.
Brian is upset because Fay beat him at tennis. Meanwhile, Roy tries to mess with Helen's mind by claiming that one of his male pilots is actually female and Joe, despite being told otherwise, can't resist flying Lowell's prized Graf Zeppelin model he's keeping in Joe's office ahead of a model airplane show.
Joe and Brian think they see a UFO. Joe is hesitant to file an FAA report, fearing that Sandpiper Air will be blacklisted. Brian goes ahead and files the report which catches the notice of an eccentric group of UFO enthusiasts. Meanwhile, Helen informs Fay she still owes her money on her lunch tab but Fay insists she paid it.
It's the gang's High School reunion. Brian dates one of his sweethearts who has a child that is the spitting image of Joe. Helen grapples with the mean girls who tormented her. Not to be left out, Antonio poses as an exchange student who briefly went to the school and Lowell discovers his shop teacher isn't all there.
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.
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.
Joe and Helen reap unpected benefits after getting a large insurance settlement for Helen's burnt down house. But Joe soon finds soon faces the task of stopping Helen's shopping spree, before it leaves them broke. Meanwhile,Brian and Casey try to find something in common and Antonio returns to Edna, "The Big Faced Girl."
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.
After fighting with Helen over the architect's plans for their new house (he wants a big screen TV in the bedroom, she wants a walk-in closet), Joe has a strange dream involving Tigers, Clowns, Roy bellying dancing and the two of them dying in a plane crash with Antonio. As one by one the dreams events come to pass, Brian tries to convince Joe to heed the dream's warnings, but he fails and soon Joe, Helen and Antonio find themselves plunging to earth in the plane...
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.
Fay quickly falls for Lyle, the dashing man she met on a cruise, but the wedding is jeopardized when Fay learns the awful truth about him. His real first name is George, just like her first three dead husbands. Armed with this new knowledge Fay decides against making it a fourth George and calls off the wedding.
A publicity disaster occurs when Antonio (running the desk while the brothers go to a hockey game) bumps the Bruins abrasive star goalie Danny "Dead End" Connelly off a Sandpiper flight to a critical game, causing the Bruins to lose. Meanwhile, winter tourism on the island takes an upswing when Casey welcomes the International Society of Masochists to Nantucket.
Sandy's return sends Joe to the psychologist, as no one believes his stories of her obsession with him. The psychologist does wonders to calm Joe down, but the real psycho is revealed when Joe meets Sandy in the vacant psychologist's office. Meanwhile, Roy, Antonio, Fay and Casey try to deal with the news they may have suffered food poisoning from Helen's tuna.
Antonio thinks his fortunes have taken a turn for the better when one of passengers hires him to be his personal chauffeur. But some overheard conversations seem to indicate that his new boss is a mobster. Meanwhile, Helen hurriedly reads "Don Quixote" when her old english lit teacher from highschool drops by for a visit.
On the verge of losing her job with the Tourism Board, Casey sees a solution when her sister city idea is accepted. But things go downhill when Brian sleeps with the visiting princess of prospective sister city Khirinan. Meanwhile, Antonio offers to take the little princesses for their hair care appointment. It turns out to be two dogs, which he promptly loses.
Antonio meets the perfect woman, but when she disappears before he can get her name, he goes on a desperate search for her, only to discover it wasn't just coincidence that she was so difficult to track down. Meanwhile, Brian impresses Helen with his ability to read women and predict the entire relationship before it even starts.
The unearthing of a 20-year old time capsule is occasion for Joe, Brian, Helen and Casey to reflect on what kind of a future they envisioned themselves having as kids. Joe dreamed of being a pitcher for the Red Sox, Brian dreamed of being a Suave Secret Agent, and Casey dreamed of being a supermodel. But only Helen's dream came true.
Casey finally catches up with the husband who abandoned her, but her rage lessens as he professes his heartfelt remorse at his desperate act. She's understanding to his sad stories of being bankrupt and shame causing him to leave in the first place...until she sees him on his yacht. Meanwhile, Roy teaches Antonio how to dance.
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.
Joe and Helen meet the next-door neighbors, Steve and Barbara, but what starts out as pleasant soon turns disturbing when Steve asks for $5000 to cover his gambling debts. Becoming increasingly paraniod after a fight Joe and Helen decide to try and make amends, only to find out their new neighbors are only on the island for the month. Meanwhile, Antonio recieves his Uncle Bernardo's personal affects after he dies. Which includes a set of perfume scented love letters appearantly from Bernardo to a certain very famous movie star of the times (Gina Lollobrigida). Hearing this Antonio suddenly becomes a suave ladies man with confidence, until he finds out his Uncle wasn't in love Gina, but Gino.
As a furious storm rages outside,Joe and Helen stop by the "Singles Mingle" to drop off Brian's wallet,intent on leaving as soon as possible to begin celebrating the first anniversary of their wedding.But news soon comes that the roads are closed due to high water and everyone is trapped.Not wanting to let everyone know they are married,for fear of their reaction,Joe asks Helen to be his bride again. Meanwhile,Fay,Roy and Casey mingle,while Antonio is offered his money back and asked to wait in the office till the party is over.And Brian tries to convince the only woman in the place he's attracted to,the sexy Bartender,that he's not a pathetic as he seems.
Antonio volunteers to man the Nantucket Suicide Hotline,it soon pays off for him when he scores a date with a caller he helped.When they meet he can't believe his eyes or his luck and keeps waiting for the other shoe to drop and for her to dump him.But the weird thing is,she never does. Meanwhile,Helen faces some new competition when a
Cord's first act as the new President of Sandpiper is to hold a meeting, informing everyone they need a "big idea".Something that drives Joe crazy, trying to get everyone to see there is no "Big Idea".But there is,Little does Roy know that he would be responsible for the "Big Idea".Mentioning to Cord that the charter business is the one, he hasn't been able to crack. So after contacting friend of his in the music business,the "Big Idea" pays off when Sandpiper becomes the charter for the singing sensation the Todds.That is until a fued breaks out and the tour is cancelled.
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 plane’s 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 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.
Brian and Helen's trip to New York to see "Rent" turns into a night mare when the theatre refuses to transfer the tickets from Helen's benefactor to her.Even worse a con-man robs them of their money and Helen is forced to compete in a drag queen contest in order to get the money to get home. Meanwhile,A bad back leaves joe in the house alone with a suddenly talkative Antonio.
Brian is surprised to find out his new girlfriend,Emily's son is already in college.Further complications ensue when Casey takes a shine to the young man. Meanwhile,Joe and Roy go to the circus:Joe to try and deal with his childhood trauma and Roy to demand an apology from the clown who humilated him in his act.
To cheer up Helen,Joe restores her old cello.While Helen is busy rediscovering her old passion,Joe and Brian discover the ages old treasure hunt they undertook when their father died isn't over yet.They and the rest of the gang are led all over New England,only to wind up back at the airport,to discover $250,000 in an old suitcase in an airport locker.
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.