RUBY, a British forty-something, reluctant mother and wannabe writer finds herself smack in the middle of a mid-life crisis, kicked off by the death of her famous, but icy mother, with whom Ruby never had closure. With her best friends from university, British DEBS and American ALICE, Ruby plans a long-awaited family vacation in Italy, where 20 years earlier the girls had a raucous and unforgettable time inter-railing.
Arriving at the country villa on Ruby’s 45th birthday, they are stunned to discover it is a swinging bachelor’s shag-palace, ill-equipped to house three couples and their six sprawling young children. The sexual accoutrements, including a suspicious swing and see-through shower outrageously positioned in the living room, make the men indulge in excessive macho-male bonding pomp. Their crude testosterone-driven jokes and bragging cause friction with their wives who find them ridiculous and unequivocally annoying.
Ruby has brought her beloved typewriter along, hoping to find time to finish her manuscript. She is devastated when she discovers that the typewriter is nowhere to be found and has been lost in transit. Her already intermittent writing grinds to a complete halt and she slips into an existential crunch. TOM, Ruby’s faithful ex-hippie husband, puts the final nail in Ruby’s coffin when he benevolently suggests she should “give up writing and get a new hobby.” As if this wasn’t enough grist for the mill, Ruby hides a secret that torments her: She fears she is pregnant with her third child.
Same time, EDDIE, Deb’s husband, has been drinking copious amounts of beer since they arrived to mask the cracks in his marriage, whilst Debs looks on, increasingly disgusted. When Debs snaps and cruelly reveals Eddie's impotence to her friends, right in front of him, he fires back by calling her a “fat cow.” Alice, an exhausted granola mom, who’s tried to carry on as if everything is fine, makes a final effort to smooth things over, but is soon pushed to her own limit when Italian husband FILIPPO, now joins ranks with Eddie in bemoaning their wives respective, general states of “disrepair.” The situation degenerates and explodes into a spectacular argument, which involves everyone and takes no prisoners. Led by Ruby, the women declare that they are, “taking a vacation from their vacation!!” – just overnight - and leave their families high and dry for a much needed break, hoping to revisit some scenes from their youth before their waist lines expand and their tits head south forever.
Debs and Alice, however, are unaware that Ruby has no plans to ever go back.
Their first stop is a fondly remembered hotel, currently a playground for “Singles Get it On and Get it Up Vacation Tours.” Ruby, now in self-destruct mode, embraces the bedlam, gets totally wasted and has meaningless, embarrassing sex with a stranger… or two… or three. Alice spots Ruby in the act and shocked, retreats to their hotel room, unseen. Debs enjoys a more innocent evening, indulging in cocktails and karaoke singing, topping off her act by careening off the stage.
The next day, Alice, while zapping through the TV channels, discovers that her high-school friend JENNIFER, a hugely successful children’s author on a world promotional tour, is staying in a nearby castle. She tries to convince her unwilling and hung-over friends to accompany her to meet Jennifer. Ruby, riled with envy, is dead against the visit as Jennifer’s successful and child-free life is everything that she secretly covets. In the end, Alice gets Debs on her side and the two wear Ruby down. She grudgingly agrees to go along for the ride.
In the meantime, back at the ranch, the men are crumbling under the strain of six uncontrollable and absurdly vivacious children. Filippo is the first to crack after a hellish barbecue the night before, trying to manage the raging fire with buckets of water while the older children merrily play, skimming frozen burgers across the pool. To top it off he wakes up in the morning, painted blue and smeared in chocolate. At his wit’s end, he calls Alice to tentatively inquire when they will return. She breaks the news that they are extending their trip to go see Jennifer. He manages to elicit from Alice where they will be lunching on route.
In a picturesque hilltop town, over a boozy meal, Alice confronts Ruby about her wild night. Ruby is ashamed but disguises her deep guilt by brazening it out and shocks her friends when she unmasks her plans to leave Tom. Alice and Debs are speechless until Ruby backtracks assuring them that she’s only joking. Alice and Debs are rattled, but take Ruby at her word.
The women finish eating, head back to their car and are just pulling out of the piazza when they are appalled to find Filippo trailing them in his car, children in tow! Impulsively, Ruby steps on the gas just as Filippo pulls alongside them. Alice catches sight of her daughter sadly waving and, overwhelmed with maternal guilt, she bangs on the dashboard, inciting Ruby to stop. The air-bag explodes and Ruby stops the car. Filippo, at the end of his rope, dumps their two small children on Alice and takes off. Ruby is mortified that their child-free time is over. The women continue towards Jennifer’s castle, their mood subdued before the children, unaware that their troubles have only just begun.