We love unearthing creative experiences across Italy. It’s highly likely this article contains links to products or services that we believe in from one of our affiliate partners – Trip.com. Mission accomplished if we’re paid for any link you click on. Read here.
The Real Tour of Frances’ Italian Midlife Makeover
If you’re already fluent in the language of “Under the Tuscan Sun,” you know this isn’t just a story about rolling hills and endless pasta. It’s about the glorious mess of reinvention, the comedy of errors that is starting over, and the peculiar magic that happens when you say yes to the improbable.
Day 1: Rome—Where the Plot (and the Pasta) Thickens
Frances doesn’t arrive in Rome seeking enlightenment; she stumbles into it, propelled by heartbreak and the dubious encouragement of friends who think a gay tour ticket is the cure for divorce. Rome, with its anarchic beauty and layers of history, is less a backdrop and more a co-conspirator. Here, every cobblestone is a reminder that reinvention is as old as the city itself.
Iconic Scene Echo: Remember when Frances, lost in her despair, absentmindedly boards the wrong tour bus, a ‘gay and lesbian’ tour? That initial disorientation is Rome in a nutshell – a beautiful maze that leads to unexpected discoveries.
Photographers, skip the postcard shots. Instead, hunt for the stories in the shadows:

- Campo de’ Fiori: Capture the hands that barter and build, not just the produce. Think of the vibrant market scenes where Frances starts to engage with local life, one tomato at a time.
- Aventine Keyhole: Peer through for a metaphor—sometimes the best views require a little squinting and a lot of faith. It’s like Frances’ tentative peek into a new life.
- Quartiere Coppedè: Let the surreal architecture echo Frances’ sense of being out of place. The whimsical, almost dreamlike structures reflect her initial disorientation.
- Galleria Sciarra: Find the interplay of colour and light, as unpredictable as Frances’ next move.
- EUR District: Seek out the austere geometry—a visual palate cleanser from the city’s usual chaos.
Where to stay? Imagine Frances, espresso in hand, plotting her escape in a hotel lobby, eyeing fellow travellers and wondering who else is running from something. Choose a spot that feels like a launchpad, not a destination.
Hotels:
Restaurants:
Getting There: Fly into Rome’s Fiumicino Airport. Take the Leonardo Express to Roma Termini (30 minutes).
Day 2-4: Cortona—Impulse Buys and Existential Renovations
Cortona isn’t just picturesque; it’s a test of endurance. Frances arrives, jet-lagged and panic-stricken, only to fall for a villa that’s seen better centuries. The ensuing renovation is less HGTV and more slapstick tragedy: plumbing that sabotages, roofs that conspire, and a garden that threatens to reclaim the house entirely. Yet, amid the chaos, connections form—awkward, endearing, and utterly unscripted.
Iconic Scene Echo: Picture Frances’ first, comically disastrous tour of Bramasole, complete with a leaky roof and questionable structural integrity. Capture that sense of dilapidated charm; the “fixer-upper” that becomes a metaphor for fixing herself.
Skip the tourist gloss and focus your lens on:
- Piazza della Repubblica at dawn, when the town stretches awake. It’s the perfect backdrop for a scene where Frances slowly begins to feel like she belongs.
- Via Nazionale, where sunlight and shadow duel across ancient stone. Reflect on the market scene where Frances buys her first tablecloth – a small victory in embracing her new life.
- Fortress of Girifalco at sunset, for the kind of view that makes you forget your overdraft. The panoramic view mirrors Frances’ expanding horizons.
- Vicolo Iannelli, where the town’s true character hides in the cracks and blooms.
Stay somewhere that lets you eavesdrop on locals debating football or politics, and eat where the menu is handwritten and the wine flows without pretence. Frances learned that happiness is found between mouthfuls of handmade pasta and half-understood conversations.
Hotels:
Restaurants:
Getting There: Take a train from Rome to Camucia-Cortona (2.5 hours), then a bus or taxi to Cortona (15 minutes).
Day 5: Positano—Escapism with a Side of Limoncello

When the villa’s chaos becomes too much, Frances bolts for the Amalfi Coast, where Positano clings to the cliffs with the same desperation she clings to hope. Here, romance is fleeting but vivid—a brief interlude with Marcello that’s more about rediscovering possibility than finding ‘the one’.
Iconic Scene Echo: Recreate the feeling of Frances’ impulsive escape to Positano. The dazzling coastal views and brief fling with Marcello signify a momentary break from the heavy lifting of rebuilding her life.
Photograph the town from the sea, where its pastel buildings tumble into the Mediterranean like a spilled box of crayons. Hike the Path of the Gods for a reminder that the best perspectives require a little sweat. And when you eat, let each meal be an act of celebration, not consolation.
Hotels:
Restaurants:
Getting There: Take a train from Rome to Salerno (2 hours), then a ferry to Positano (70 minutes).
Day 6-7: Montepulciano—Building Something That Lasts
Back in Tuscany, Frances finds her footing on Montepulciano’s limestone ridge. The villa, once a monument to regret, becomes a stage for new beginnings—a wedding, a gathering, a home. The town’s medieval walls and underground wine cellars are less about history and more about the layers we build (and rebuild) in our own lives.
Iconic Scene Echo: Channel the heartwarming scene of the impromptu wedding at Bramasole. The villa, now a home, symbolizes Frances’ transformation from a heartbroken tourist to the heart of a makeshift family.
Capture the changing light in Piazza Grande, the hush of wine cellars, and the daily rituals that make a place feel like home. Stay somewhere with a view that reminds you why you came, and eat with strangers who might, by dessert, become friends.
Hotels:
Restaurants:
Getting There: Take a train from Rome to Chiusi-Chianciano Terme (1.5 hours), then a bus to Montepulciano (30 minutes).
For those retracing Frances’ journey, the real adventure isn’t in the scenery or the food (though both are spectacular). It’s in the willingness to be undone and remade, to find humor in disaster, and to discover that sometimes, the best parts of life are the ones you never planned.

