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 paranoid 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 receives his Uncle Bernardo's personal affects after he dies, including 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 with Gina, but Gino.

Brian's vow to find a deeper, more meaningful relationship is tested by beautiful but dumb Dani. Meanwhile, Joe tries to deal with the fact that one of his best friends didn't invite him to his wedding.

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—for her to dump him.

When a medical courier leaves his package in the terminal on Halloween Eve, the gang scramble to find him before time runs out.

Casey encourages Brian to use his insurance money to open a martini bar, offering to help manage it. But things go awry immediately when the first customer through the door slips and falls on the floor. Brian's problems are compounded when he learns Casey never got insurance.

A financial crisis forces Joe to seek out an investor for Sandpiper. He thinks his luck has changed when businessman Jonathan Clayton comes to the island. But he soon informs them he doesn't invest in companies; he buys them.

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 Roy mentions to Cord that the charter business is the one, he hasn't been able to crack. Roy's "Big Idea" pays off when Sandpiper becomes the charter for singing sensations, the Todds.

When Cord chickens out on delivering a presentation before his father's board of directors, Joe and Brian must deliver it. Meanwhile, hanging in the men's, Helen learns a nasty secret: Cord was expected to fail at Sandpiper for the tax write-off.

Another odd Christmas falls on Nantucket as Antonio drives a nun around in search of a vision she saw in a dream, while Joe plays reluctant host to feuding brothers Lou and Harry, and a little last minute shopping ends up trapping Fay, Helen and Casey.

Roy falls for talk show host Mary Pat Lee, but discovers she used confidential information to ambush Joe and Helen on her show. Meanwhile, Brian pays Casey to run errands for him.

Joe and Helen deal with a crooked vacuum cleaner salesman charging them to repair a vacuum originally sold with an "eternal" guarantee. Meanwhile, Brian gets close to Roy to get closer to his niece.

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. This leaves 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 George's, 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, 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 nightmare 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.

Kicked out by Joe and Helen, Brian and Casey move into a new home with Antonio. Meanwhile, Joe and Helen's fling with nudism has them being threatened with blackmail when the neighbor kids snap pictures of them.

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 for them.

When Fay goes on vacation, the Hacketts hire a beautiful woman to fill in at the counter. Brian finds her distressingly distracting, while Joe and Helen have uneasy dreams about her. Meanwhile, Casey helps Antonio get a job at the department store, only to see him promoted ahead of her.

Roy invites Joe and Helen over to his house on an important night for him: the introduction of his girlfriend to his mother. But when he's dumped before the fateful evening, Helen reluctantly fills in. Meanwhile, Brian passes on his cold to Casey before her big date.

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 young Shawn. 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.

When a long time rival drops out of a boxing tournament, Joe finds himself matched up against Brian. But what starts out as a friendly competition gets decidedly unpleasant.

To cheer up Helen, Joe restores her old cello. While Helen is busy rediscovering her old passion, Joe and Brian discover that 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 and 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 to use 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 Caribbean in order to run Sandpiper for one year while Joe and Helen are away in Vienna.