When life gives you lemons, make limonata: How lockdown upended a Torontonian’s Roman holiday — and gave her a business idea

Back in April 2019, marketing pro Zoe Shapiro bid arrivederci to her downtown Toronto loft, packed up her life and her mini aussie shepherd, Chutney, and hopped on a plane to realize a long-time dream: a year in Italy. She could do her consulting work from anywhere, so why not the land of Vespas, bellinis and cacio e pepe?

As a movie nerd growing up, she’d had her first unforgettable glimpses of the country in “Stealing Beauty” and “The Talented Mr. Ripley.” “Italy really lodged itself in my brain from a very young age,” says Shapiro, an avid traveller whose clients have included the Drake Hotel Properties and the Broadview Hotel.

But despite having a passport stamped with solo adventures, she hadn’t done a trip quite so ambitious. Shapiro expected that the dramatic change of scenery — and the sense of boldness it required to move to a country where she knew nobody and only a smattering of the language — would push her in new directions. Little did the self-described “stubborn, obsessive planner” know what an understatement that would be.

She flitted through Bologna, the Tuscan countryside, Palermo and elsewhere, before ensconcing herself in an Airbnb in Rome. Her days were spent strolling museums, learning Italian from a nun at the Vatican and meeting new friends over aperitivo.

Just as Shapiro’s bucket-list sabbatical should’ve been nearing its end, the pandemic tore into town. By March, a national lockdown was announced. “My first instinct was, OK, put me on the first flight,” says Shapiro, who booked a ticket to Toronto, set to depart just two days later. That flight — her last chance to leave — was cancelled, stranding her indefinitely.

But when life gives you lemons, make limonata. “At first, I was stewing and then I was plotting,” recalls Shapiro, who had also wrapped up her work contracts right around then, freeing up time to scheme.

“I don’t want to minimize what has been a really tragic event,” she says of the pandemic, “but the silver lining was experiencing Rome this past year, more quietly. It’s just a completely different city, like Rome for the Romans.”

The first time Shapiro had gone to Trevi Fountain, pre-lockdown, there was a crush of tourists, extending 10-plus people deep, all around the iconic Baroque spectacle. When she returned mid-pandemic, she was alone, save for her faithful sidekick, Chutney. Wandering the suddenly sleepy city, through the jarringly empty Piazza Navona and St. Peter’s Square, was a once-in-a-lifetime experience.

With everything in limbo, Shapiro began to rethink what she really wanted to do, and the answer wasn’t so much a pandemic pivot as the obvious outcome of her passions: starting her own travel company in Italy.

Last month, on the two-year anniversary of touching down in the country, she launched Stellavision Travel, specializing in small-group tours for women, tailored with her insider’s eye for truly under-the-radar gems. “In Italy, the hits are so well known,” she explains, “so you really have to scrape and scour and hunt.” The trips are all-inclusive, and in the age of Instagram, that means they come complete with a professional photographer.

Among the many things that Shapiro has learned to appreciate in Italy, the life-changer has been letting go of meticulous plans. Last year, she booked an overnight ferry to Palermo, Sicily, and arrived at the port only to learn it had been delayed until 2 a.m.

With seven hours to kill, she spontaneously drove north to Maremma, Tuscany, chancing upon a large-scale installation by artist Massimo Uberti, just standing in the landscape: neon lights spelling out “Spazio Amato” (loved space). “It just felt fortuitous,” says Shapiro. Later, heading down a narrow laneway, she spotted people peering through binoculars. “I pulled over and asked what they were looking at, and there were wild flamingos in the distance,” she recalls. “I ended up happening upon the most magical evening.”

Shapiro has a permanent memento of that serendipitous moment, a flamingo tattoo on her back. It’s a reminder of what has become her personal motto: “When you stop expecting or forcing something to go a certain way, it will turn out so much better,” she says. “If the road diverges, as my life has now really done, just be open to it. See what opportunity is there.”

When in Rome (or Florence or Venice or Palermo)

Zoe Shapiro offers a few of her favourite spots in Italy.

Rome: L’Archivio di Monserrato (150 Via di Monserrato): “The modernist painter Cy Twombly has a long history entwined with Rome. His daughter-in-law, Soledad, owns a stunning shop called L’Archivio di Monserrato in centro that offers an array of clothing and curated textiles from around the world. If you happen upon Soledad, you might even be lucky enough to get a tour/peek at her basement’s treasures — and modernist masterpieces.”

Florence: Santa Maria Novella Pharmacy (16 Via della Scala): “Attached to the famed Santa Maria Novella church, this magical marble apothecary is thought to be the oldest pharmacy in the world. We love to imagine the recipes for tinctures and concoctions passed down for 800 years, since the monks first started experimenting in their herb garden. Decidedly more luxe now, you can pick up creams, candles and much more, all in beautiful packaging. The bath salts are our personal favourite. Even if you’re not shopping, the store is a treasure trove of artifacts, frescoes, statues and history, well worth a visit.”

Venice: Vino Vero (2497 Fondamenta Misericordia): “Not just our favourite wine bar in Venice, this spot is in contention for our favourite in the whole country. Which is saying something. Come for the selection and knowledgeable pours; stay for the assortment of droolworthy cicchetti — the local take on snack food. At Vino Vero, meaty, fish-based and vegetarian options are arranged as beautifully as jewelry under a vitrine and pair perfectly with our favourite glass of Friulano wine.”

Palermo: Pasticceria Cappello (68 Via Colonna Rotta): “The Sicilian sweet tooth is well documented and much appreciated! You’ll find countless cafes to sample granita and gelato, cannoli and cassata. But for their dolce, the locals head to Pasticceria Cappello. While it’s only a 10-minute walk from Palazzo dei Normanni, it’s out of the city’s centre and most tourists would miss it. You shouldn’t!”

Excerpted with permission from Stellavision’s free mini city guides, downloadable at stellavisiontravel.com. The Star understands the restrictions on travel during the coronavirus pandemic. But like you, we dream of travelling again, and we’re publishing this story with future trips in mind.