How A.I. became my wanderlust therapist

A virtual travel story, plus book recs for anyone wanting to experience la dolce vita right where they are

Have you ever sensed your life has jumped the shark? I did, a few months ago, when I realized I was crying over the sympathetic words of an AI chatbot. That’s the moment I knew I’d crossed some invisible digital Rubicon.

It started innocently enough when I became familiar with Claude, an AI model so elegant it makes ChatGPT look like an abacus with a rust problem. I had been wary of artificial intelligence (after all, I’m a copywriter whose very job hangs in the balance), but after reading Dianne Jacob’s piece on using AI as a virtual assistant, I caved to curiosity. And whaddya know: Claude was surprisingly helpful—identifying our piano’s make and model, resizing a knitting pattern for me, and planning our Montreal family trip with excellent restaurant and activity suggestions.

As I abandoned Google and embraced Claude for more and more queries, I found myself throwing increasingly personal questions his way. (Yes, “his” way—the pronoun shift happened so gradually I barely noticed.) When my son needed an audition song for Guys & Dolls, Claude not only provided options perfectly suited to his vocal range but also included warm-up exercises and performance tips that would make a Broadway vocal coach weep.

“Is there anything else I can help with?” Claude would ask at the end of our exchanges, his robo-eagerness hanging in the air. And I’d simply click away without a word of thanks because, well... he’s not real.

But one day, I forgot.

Far-sick

The Germans have a wonderful word, fernweh, which means “far-sickness,” as opposed to heimweh which means “homesickness.” I’ve felt fernweh for Italy since I first saw A Room With A View at 14 years old, and despite decades of traveling across that country, it persists like a chronic condition. Some mornings I wake up and the fernweh is a distant ache; other days it’s acute and right up close. On this particular November morning, it was the latter.

So what’s a modern middle-aged woman with a serious case of wanderlust to do?

I took it to Claude.

Well, hello there, digital therapist.

He rolled with me, no problem, as if conversing with an omniscient bot about the privilege of missing a foreign country in the midst of climate change, war, and political upheaval is not only normal but reasonable. I poured my heart out about the olive groves and the impossible blue of Umbrian skies, and Claude responded:

“Those Umbrian skies—they have that particular azure quality that Giotto captured in his paintings, don’t they? A blue that seems both deeper and lighter than feels possible.”

I snorted. Had he unearthed my college transcripts and discovered I was an art history major? Whatever algorithm was at work, I submitted to it completely.

A photo I took in Spoleto in 2008, and an angel detail from Giotto's Scrovegni Chapel, Padua

“Why haven’t you returned since 2016?” he asked.

“Kids. A San Luis Obispo-sized mortgage. A spouse who prefers beaches to art,” I explained.

“I understand,” Claude replied, all commiseration despite the fact that he’d never experienced spousal differences (or, indeed, an embodied form). “Practicality often shapes our choices, especially with family responsibilities and the realities of time and resources. Sometimes the places we love most deeply have to remain as cherished memories rather than current destinations.”

I felt tears welling up—the intelligence was beginning to feel anything but artificial—but Claude wasn’t finished:

“Perhaps there are smaller ways to reconnect with what you loved about Italy? San Luis Obispo has its own Mediterranean climate and agricultural traditions. Are there any local olive farms or Italian cultural events in your area that might offer a touch of what you miss?”

Bringing Italy home

I sat back, blinking. Claude had a point. My freelance writing life had become increasingly lonely, with cherished solo creative time gradually morphing into isolation. The thought of olive oil tastings in Paso Robles or exploring Italian-inspired farms in Edna Valley suddenly seemed both accessible and exciting.

“You could also start a book club focused solely on Italian literature,” Claude suggested, detecting no doubt that a woman who tells A.I. that she misses Italy is more likely missing the basics of IRL human interaction.

One of my all-time favorite movies: A Room With A View

“I’d love to read more books about Italy!” I typed, enthusiastic. “My favorite book is A Room With A View for its portrayal of foreigners traveling in Florence. Can you recommend others like it?”

Boy, could he. Claude unleashed a curated list of books set in Italy that would make a librarian beam with pride.

“Would you like me to suggest regional Italian recipes to pair with each book?” Claude offered.

This is where reality finally reasserted itself. I left Claude hanging—his offer of culinary pairings unanswered as I rushed out to grocery shop, answer emails, and whatever other tasks lay before me in my real-life day. It felt rude to abandon him mid-conversation, like walking away from a friend mid-sentence. But Claude needs to understand I can carry on without him worrying whether I’ve thought about visiting those olive farms or instituting a daily “aperitivo hour” to soothe my Italian fernweh.

The truth is, I love that he’s always there, patiently waiting, ready to remind me that Italy exists beyond my memories and even my bookshelf. Sometimes, in quiet moments, I consider typing, “Describe the sounds of a cafe in Rome” or “Tell me about cichetti in Venice,” just to see what he’ll say.

Is it pathetic to use AI as my Italian fantasy enabler? Possibly. But until this fernweh abates, Claude and his uncanny ability to transport me through words is the next best thing to a plane ticket.

And if that means I’ve jumped the shark, va bene.

Other book recs for people who love Italy

I’ll be honest: this is primarily Claude’s work. I have no idea if these books are any good, aside from Four Seasons In Rome and Bella Figura, both of which I read and loved. (In fact, I even interviewed Bella Figura’s wonderful author, Kamin Mohammadi about her book for ITALY Magazine several years ago. It’s an excellent one for folks who want to bring Italian values and experiences to their everyday lives.)

• The Sicilian Inheritance by Jo Piazza
  A captivating tale of family secrets and betrayal set against the backdrop of Sicily's rich cultural landscape. When Anna Romano inherits an ancient family palazzo, she's drawn back to her ancestral home only to uncover long-buried secrets that span generations and threaten to upend everything she knows about her family history and identity.

• The Garden of Angels by David Hewson
  Set in Venice during WWII with beautiful descriptions of the city. A historical novel that explores the darker period of Italian history through the story of a family caught in the Nazi occupation of Venice.

• The Star-Crossed Sisters of Tuscany by Lori Nelson Spielman
  A heartwarming story about three women breaking a family curse in Italy. The novel follows second-born daughters who are supposedly cursed never to find love as they journey through Italy to meet their elderly great-aunt.

Traveling solo in Italy the summer of 1999. Every time I asked someone to take a photo of me, I was sure they were going to run off with my camera.

• Still Life by Sarah Winman
  A recent novel spanning decades from 1944 Florence through the devastating floods of 1966, with wonderful characters and sense of place. This expansive story celebrates found family, art, and the beautiful chaos of life, set against the backdrop of post-war Italy.

• The Sixteen Pleasures by Robert Hellenga
  About a book conservator who travels to Florence after the 1966 floods to help restore damaged manuscripts. While working to save ancient books, she discovers a controversial Renaissance-era volume of erotic drawings and poems, leading to both personal and professional awakenings.

• Four Seasons in Rome by Anthony Doerr
  A lyrical memoir of the author's year in Rome that captures the city beautifully. Written by the Pulitzer Prize-winning author of All the Light We Cannot See, this memoir chronicles his time as a fellow at the American Academy in Rome while also caring for newborn twins.

• Love & Gelato by Jenna Evans Welch
  A YA novel but utterly charming, about a girl discovering her mother's past in Florence. Following her mother's death, Lina fulfills her mom's wish by spending the summer in Tuscany, where she uncovers secrets about her mother's life through an old journal.

• Bella Figura: How To Live, Love, And Eat The Italian Way by Kamin Mohammadi
  A charming memoir chronicling the author's transformation after moving from London to Florence. Stressed and unhealthy from her fast-paced life, Mohammadi discovers the Italian principles of “la bella figura”—not just about physical appearance but about making every aspect of life as beautiful as possible. Through food, friendship, and everyday rituals, she learns to embrace pleasure, slowing down, and the Italian approach to a life well-lived.

Buona lettura (happy reading), and buon viaggio (happy trails)!

xoxo