Tuscany, Castellina in Chianti: Big Dreams

Yes, in Italy. Where is it? What is it? And why should you care? Read on.

(One quick note: a 5pm meeting in Tuscany is an 8am meeting in Seattle — same day.)

For me, Tuscany started almost two decades ago. Coming here now feels like the Steve Jobs quote: you can’t connect the dots looking forward - only looking back. Let’s unpack…

The beginning: a airplane magazine and a chef

In 2005 I’d fly Horizon Air (Alaska). Onboard was the Alaska Airlines magazine, which I loved because it featured ads from local Seattle businesses. (Side note: Daniel and I even sent 11x17 posters of ourselves to some of those businesses asking them to become customers — scrappy days.)

One ad stood out: a chef in a crisp white coat holding a half-full glass of wine. He was a big man — in presence, in life, and as I’d later learn, in dreams. I told myself, the day I meet that chef and call him a friend, I’ll know I’ve “made it” in Seattle.

That chef was Mauro Golmarvi.

Today, we’re in Tuscany with Mauro, his wife Connie, and their estate, Villa Gran Sogna — which in Italian means Big Dreams. If you’ve ever crossed paths with me, chances are you’ve crossed paths with Mauro too, whether at his restaurant Assaggio in downtown Seattle or through one of the many stories tied to it.

But this isn’t about Seattle. This is about Tuscany.

Where and what is Tuscany?

Tuscany is a region in central Italy — about an hour from Florence (the capital) and three hours from Rome. It’s famous for rolling hills, vineyards, olive groves, cypress trees, bistecca (steak — look it up), wild boars, and timeless towns.

It includes Siena, Pisa, Lucca, Arezzo, San Gimignano, and world-class wine regions like Chianti, Montalcino, and Montepulciano. (Did you know Chianti is just another name for Sangiovese?)

Many visitors will choose Florence or Siena and make day trips into the countryside. My recommendation: don’t. Stay in the countryside — but pay close attention to where.

If the movie Under the Tuscan Sun is playing in your head, you’re not wrong.

Tuscany is for gathering. Rent a villa, stay a week. It works as a couples’ trip, but I lean group. The sweet spot for a stay? Five to seven days.

You can fly into Rome or Florence and rent a car easily through SIXT. We stayed in Castellina in Chianti, which feels more centrally located than other towns, roughly halfway between Florence and Siena. Note: every gas station has an espresso bar and if you are unsure if one does stop at Auto Grill. Ashley says the best glass of wine she had was in one of those gas stations on our way from Rome to Castellina.

Here’s some perspective: Florence’s population is almost 400,000. Siena’s is 60,000. Tuscany’s total region holds about 3.7 million people. Pisa — and yes, the Leaning Tower — is also in Tuscany. Staying in Florence versus the countryside is like staying in San Francisco when Napa and Sonoma are only an hour away. Same region, very different experience.

For us — living in three major U.S. cities already — countryside life appealed. A town like Castellina offers space to paint, write, sit under a tree, watch a movie, and wake up among ancient vines. City life has its pull too: Florence or Siena gives you that mix of energy and proximity to the countryside. It’s really about the experience you want.

Being comfortable under the lights of an olive tree, having a sloooow breakfast, lunch, and dinner — sometimes even skipping dinner in favor of brunch — is not uncommon here. If the go-go-go pace of vacation is what you crave, pick one of the cities. But if you have gran sogna (big dreams) and romanticize carving your rental car along winding Tuscan roads, pick the countryside.

What to do in Castellina in Chianti

Side quests are part of the fun: mopeds, wine tasting, a dip by the pool, a Ferrari drive, a Siena day trip, vintage shopping, painting, writing, long lunches at ristorantes, simple dinners at osterias, even gas station espresso (can you tell we loved it).

A long lunch in Greve in Chianti? Chef’s kiss.

Early morning walks along rolling vineyards? Epic.

A picnic with friends — or even doomscrolling poolside? No judgment.

Sometimes the best thing you can do here is sit, breathe, and think — especially against the echoes of the ancients.

Still, one of the most Italian things you can do is nothing. There’s a saying — il dolce far niente — the sweetness of doing nothing. And the small towns of Tuscany reward that far more than any big-city itinerary.

Why should you care?

Because it’s immersive. You walk, sip, and breathe lands layered with history, art, and philosophy. Tuscany is the cradle of the Renaissance.

Starting in the late 14th century, wealthy families like the Medici invested in art, science, architecture, and humanism — sparking a cultural revival that spread across Europe.

The Medici were both ruthless power brokers and visionary patrons. They bankrolled Leonardo da Vinci and Michelangelo (fun fact: Bill Gates bought Leonardo’s sketchbook for ~$25 million). They produced Popes, supported Galileo, and even after their bank collapsed, their influence still lingers in Florence’s culture.

I brushed up on this before we came, watching Stanley Tucci’s episode in Florence where he and a local chef explained how the Medici influence even reached the cattle — hence the steak reference earlier. That rabbit hole added new depth to the trip. Having Mauro as our guide, translator, and larger-than-life “uncle” added the rest.

The patrons of artists allowed their influence to reach cities around the globe including modern 19th century New York City in collections at the Frick to the Met. This single point is drawing us closer to connecting the dots to old masterworks and how art plays a cultural role - we can discuss that in a later post.

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Comparisons & Food

It’s tempting to compare Tuscany to Napa, Eastern Washington, or Chile. Vineyards, rolling hills, sunshine — sure, the parallels are there. But Tuscany carries two things those regions can’t: its Renaissance heritage and its food.

As for the food? That’s for you to discover.