Nearly thirty years ago, I picked up a copy of the book Under the Tuscan Sun by Frances Mayes. I was nineteen years old, had never been to Tuscany, and had no idea that one book would quietly plant a seed that would grow for decades. At that point, we had been living in the States for just about eight years, I was still feeling somewhat “homesick” for Italy, so I gravitated towards Italy-inspired books and TV shows.

As I turned each page in this book, I found myself imagining stone houses, winding medieval streets, sunflower fields, and a slower, simpler way of life. I remember thinking, “Wouldn’t it be incredible to own a home in Tuscany someday?”

It seemed like one of those dreams that belonged in the “maybe someday” or “wishful thinking” category. Because at 19 years old, everything still feels possible, doable. There’s so much time left!

Life happened. I built a career in healthcare. I cared for family. Eventually, I started a business. I wrote cookbooks. I’ve had the distinct honor of leading hundreds of travelers through Italy. The dream never disappeared, but it patiently waited its turn.

Then, nearly three decades after its planting, that little seed blossomed.

Today, I split my time between Boston and Cortona. Every time I unlock the front door to my home here, I still have moments where I can’t quite believe this is real.

People often ask me why I chose Cortona instead of Florence, Siena, Lucca, or one of Tuscany’s many famous villages.

The answer is simple.

Cortona felt like home. But the purchase was also strategic! Cortona is close enough to the Rome International Airport that I don’t need a connecting flight! If I’m going to be going back and forth several times a year, this convenience is second to none. No layover! No connections! No wait times at the airpot for connecting flights!

More Than a Beautiful Hill Town

Of course, Cortona has everything visitors hope to find in Tuscany. Ancient Etruscan history, medieval architecture, spectacular countryside views, charming piazzas, family-run restaurants, artisan boutiques, and enough winding alleyways to keep you happily lost for days. It became internationally famous after Under the Tuscan Sun, yet somehow it has managed to preserve its authenticity in a way many destinations struggle to do.

But what truly captured my heart isn’t something you’ll find in a guidebook.

It’s everyday life.

Most mornings begin with me taking my dog, Trixie, for a walk through the town. Shopkeepers are raising their shutters. The scent of fresh cornetti drifts from the cafés. Church bells echo through streets that have existed for centuries. New friends stop to chat in the piazza before heading off to work. Thursdays and Saturdays are market days, so those are our favorite days of the week.

Nobody seems to be in quite as much of a hurry as we often are back in Boston.

That’s what I love most about Italy.

Life isn’t measured by how much you accomplish before noon. It’s measured by conversations, shared meals, long lunches, beautiful views, and taking the time to enjoy ordinary moments.

The Italians even have a phrase for it: la dolce vita.

It’s not about luxury. It’s about presence.

Why Slow Travel Changes Everything

I’ve realized over the years that so many travelers unintentionally rush through Tuscany. They spend one night here, two nights there, checking famous towns off a list before moving on to the next destination.

They certainly see lots of Tuscany.

But they rarely experience it.

One of the philosophies that has shaped my company from the very beginning is something Italians have understood forever: piano, piano. Slowly, calmly.

When you get to know one place, something changes. You begin recognizing faces at your favorite café. You stop worrying about schedules and suitcases. You settle into the rhythm of the town instead of simply passing through it.

That’s exactly why most of my tours are built around a single home base. Rather than spending precious vacation time constantly packing and unpacking, we immerse ourselves in one area and truly get to know it. It’s a slower, richer way to travel that allows you to experience Italy rather than simply check it off a bucket list.

Experience Tuscany the Way I Do

It was only natural, than, that when I decided to create my newest Tuscany adventure, Cortona became its heart.

My Springtime Under the Tuscan Sun journey isn’t about racing across Tuscany trying to see everything in one week.

It’s about discovering the Tuscany that made me fall in love with this region in the first place.

We’ll spend seven nights in a beautiful boutique hotel right outside Cortona’s historic center, allowing you to experience the town much the way I do. Wake each morning to one of the finest hotel breakfasts in Italy, actually an award-winning breakfast, before wandering the quiet streets as the town slowly comes to life. Return each evening to the same welcoming home base, where you can settle into the rhythm of daily Tuscan life.

From Cortona, we’ll venture out on carefully chosen day trips that complement, rather than compete with, our home base. We’ll spend a delicious day eating our way through Florence with a guided food tour, stroll the elegant streets of Montepulciano, discover the beautiful city of Arezzo, explore picturesque Lake Trasimeno, and cross into neighboring Umbria, proving that some of Italy’s greatest treasures lie just beyond Tuscany’s borders. Each evening, however, we return “home” to Cortona.

Of course, food remains at the center of everything I do.

We’ll share unforgettable meals, meet passionate local producers, taste incredible wines, enjoy authentic Tuscan flavors, and spend time around tables where conversations often become just as memorable as the food itself.

Because that’s the Italy I want you to know. Not the Italy that exists for tourists.

The Italy where families have been making pecorino for generations. Where olive oil isn’t simply purchased—it’s discussed. Where lunch is never rushed. Where the owner of the trattoria comes out to ask if you enjoyed your meal because they genuinely care.

Those moments can’t be manufactured. They simply happen when you slow down enough to let them.

Spring Is Tuscany at its Finest

Spring is perhaps my favorite season here. The countryside turns an almost impossible shade of green. Wildflowers blanket the hillsides. Outdoor cafés fill with locals enjoying the first warm afternoons of the year. The days are comfortably warm without the intense summer heat, making it the perfect time to wander medieval streets or linger over a glass of wine in the piazza. Spring has long been one of Tuscany’s most celebrated seasons, as villages come alive with festivals, markets, and the energy of renewal after winter.

A Place That Keeps Calling Me Back

I’ve now been calling Cortona my part-time “home” for about 18 months, yet, it continues to surprise me.

I’ll stumble upon a tiny wine bar hidden down a side street. Discover a new artisan I’ve somehow walked past dozens of times. Watch an impromptu concert in the piazza. Strike up a conversation with someone who’s lived here their entire life.

The town reveals itself little by little. I hope to never grow tired of its revelations.

It’s no longer simply the place where Under the Tuscan Sun was written. It’s the place where one of my own dreams came true. And now, I’d love nothing more than to share it with you.

Maybe you’ll leave with beautiful photographs, wonderful recipes, and a few extra pounds from all the incredible food.

But my hope is that you’ll also leave with something far more valuable: an appreciation for slowing down, living more intentionally, and discovering why this little hilltop town has captured hearts—including mine—for generations.