Joe and Helen return from their honeymoon in Jamaica to receive bad news: a night of passion between Brian and Casey in Helen's house resulted in a devastating fire. That leaves Brian kicked out of both the house and Sandpiper by Joe.

When digging through the rubble of Helen's home, Brian and Casey unearth a suitcase and photograph that had been the Hackett brothers' 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 Harrison Kingsbury's death in Miami is occasion for celebration at Sandpiper, as Kingsbury's oldest daughter hires the Hacketts to bring the body back to Nantucket for the memorial. But the brothers fly the wrong body back to the island, and it's up to Joe to impersonate the late Kingsbury at the funeral.

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, rather than see the gangster released and have a chance to kill again.

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.

Joe and Helen reap unpected benefits after getting a large insurance settlement for Helen's burnt down house. But Joe 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."

Joe and Helen's initial fortune at landing famous architect Y.M. Burg to design their new house soon turn sour as he suggests a house shaped like a giant "7." Meanwhile, Brian hires a new mechanic, Budd Bronski, who attempts to live down a previous "incident."

When Joe is too busy with his new wife to spend time with him, Brian turns to food. He 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 belly-dancing, and the couple 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. Joe, Helen and Antonio soon find themselves plunging to earth in the plane…

Nothing goes right at Helen's christmas party: Joe wants to hit the road to head for the slopes before they are snowed in; Antonio gives but does not receive; Roy misses his mother; Budd tries to be social; and Casey invites Carlton's annoying nephew Lewis.

Joe and Helen volunteer to babysit but it's far from the learning experience that they hoped it would be. Meanwhile, Casey gets a big time Hollywood star to come to the island to appear in her Nantucket Tourism commercial.

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.

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 marrying a fourth George and calls off the wedding.

A publicity disaster occurs when Antonio covers for the Hacketts so they can go to a hockey game. Antonio 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.

Brian falls in love with a woman while flying her to Nantucket for her wedding. Meanwhile, Antonio has mixed feelings after finding out Roy is dating Edna, "The Big Faced Girl."

When news arrives that Davis Lynch has re-surfaced, Helen recounts the tale of how she never broke off her engagement with him, then tries to break the news to Davis, while not alerting Joe.

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 Literature teacher from high school 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.

The contractor Joe and Helen hires to build their new house falls apart when his wife kicks him out, and the Hacketts try to rebuild his confidence and get him back to work. Meanwhile, a vacationing George Kennedy is bothered by an annoying fan: Brian.

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.

Joe faces a moral dilemma: can he lie to Helen so he can go to a strip club with Brian? To soothe his conscience, he volunteers some time at the Golden Crest retirement home, but ends up taking one of the residents with him to the strip club. Meanwhile, Fay and Antonio write their own eulogies.

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 bankruptcy and shame causing him to leave in the first place…until she sees him on his yacht. Meanwhile, Roy teaches Antonio how to dance.