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Wealthy socialite Charlotte Cartwright and her dear friend Alice Pratt, a working class woman of high ideals, have enjoyed a lasting friendship throughout several decades. Recently, their lives have become mired in turmoil as their adult children’s extramarital affairs, unethical business practices, and a dark secret threaten to derail family fortunes and unravel the lives of all involved. Charlotte and Alice decide to take a breather from it all by making a cross-country road trip in which they rediscover themselves and possibly find a way to save their families from ruin.

When a straight-laced couple that has fun with a rowdy couple on vacation in Mexico return to the States, they discover that the crazy couple they met in Mexico followed them back home and decide to play tricks on them.

Newly married Marcus and Emily invite Ron and Kyla, who are also newly married with a baby, to join them at a Caribbean resort, where Marcus is meeting with the owners about a construction contract for a Chicago hotel. But when the party begins the couples' relaxing vacation quickly becomes a wild adventure.