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.

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.

Joe and Brian, in heated competition, pull out all the stops in a transparent attempt to get closer to Alex.

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 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.

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.

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.

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.

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.

Fay encourages a retired pilot to complete his trip around the world.

Joe and Helen find themselves being rushed to the altar when Brian and the jet-setting woman of his dreams talk them into a double wedding.

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."

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.

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.

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.

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.

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.

Brian sets Joe up on a date with a woman who's been with every man on the island.

When Brian's old friend shows up and they resume their wild, partying lifestyle every night, Alex grows increasingly neglected. Lowell takes in his idol, over-the-hill television superhero Big Strong Man, who takes advantage of his hospitality.

After receiving $25,000 from the family trust fund, Lowell invests the money in an old wax museum. Despite everyone's doubts, Lowell renovates the museum. but he comes to realize it won't be easy at the lackluster grand reopening of "Lowell Mather's House O' Wax". When news comes of a disastrous fire at the museum, Lowell is determined to start again from scratch.

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.

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'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.

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.

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.