Wedding planner Rosie is struggling with her grey, rain-soaked life in Ireland. When her landlord suddenly doubles the rent, Rosie is left with no choice but to pack up her family, two dogs, and possessions into a 20-year-old camper van and head off in search of her own happy ending in sunny Italy. While Rosie is determined to create the perfect life for her family in Italy, despite a hurricane, a raucous family dispute, and a little thing called a global pandemic to top it all off, she begins to realize that the Italian dream may be too big for her.

After ten years of loyal service, Daisy Butterworth has been made redundant. Like any clever woman, she knows the cure to redundancy is a little too much wine and her best friend. Only the next morning, Daisy has more than a hangover...she has a whole new house—in France! Seeing this as an opportunity instead of a disaster, she’s excited about finally moving to France, just as she and her husband always dreamed of. However, Daisy is in for another surprise. Despite planning to move there for over 20 years, her husband never actually intended to go.

When Elizabeth drops her beloved only daughter off at college, she holds back the tears…fighting her worries about an empty nest with the thought of all the adventures that she and her husband Joel can now enjoy together. But as soon as they sit down to eat dinner that evening, Joel drops a bombshell. He wants a break. Searching for an escape, Elizabeth discovers an apartment in Rome that is only available for three months rental to ‘an English woman of a certain age’.

In the 1970s, the ultimate trip for any backpacker was the storied “Hippie Trail” from Istanbul to Kathmandu. A 23-year old Rick Steves made the trek, and like a travel writer in training, he documented everything along the way: jumping off a moving train, making friends in Tehran, getting lost in Lahore, getting high for the first time in Herat, battling leeches in Pokhara, and much more. The experience ignited his love of travel and forever broadened his perspective on the world.

Workaholic, career-obsessed Francesca is fiercely independent and successful in all areas of life except one: family. She struggles to make time for her relationship with her teenage daughter, Allegra, and the two have become practically strangers to each other. When Allegra hangs out with a new crowd and is arrested for drug possession, Francesca gives in to her mother's wish that they take one epic summer vacation to trace their family roots in Italy. What she never expected was to be faced with the choice of a lifetime....