Riding, Eating & Drinking Our Way Through Tuscany.
We’ve lost count of how many times we’ve been to Italy, but every trip seems to deepen our love for the country’s food, wine, and way of life. Tuscany, in particular, keeps calling us back. We’ve now visited three times, and those experiences played a big part in inspiring our 2024 Flight Path Sonoma Valley Sangiovese.
Our first visit was on a Trek Travel cycling trip through the Tuscan countryside - Tuscany Bike Tour: Cycling Through Italy’s Most Beautiful Views. The second was for my 50th birthday, when we gathered friends from Atlanta, Santa Cruz, and Park City for a week of riding the famous strade bianche - the white gravel roads that wind through vineyards, olive groves, and hill towns. We rented a beautiful villa we found on Airbnb and it was even better in real life than the pictures. Normally, we don’t go back to the same place twice, but Antico Machionne became one of those places you never quite forget. Less than two years later, we returned to the same villa for a week-long food and wine retreat hosted by chef Massimiliano Giovannini and his wife Jordana. It was every bit as magical as it sounds.
Across those three trips, we have collected favorite places, meals, bottles, and memories. Here are a few worth sharing.
Where to Stay: Antico Macchione
If you’re traveling with a group, the carefully restored Antico Macchione is special - Nestled among the rolling hills, your sanctuary style villa awaits. Tucked into the rolling hills, it’s the kind of villa that makes you want to extend your trip immediately. Eight bedrooms with en suite baths, inviting indoor gathering spaces, sweeping outdoor terraces, and a fully equipped kitchen make it ideal for family or friends.
Our host, Cally, is also an amazing yoga instructor, and the property includes a beautiful studio where she teaches guests. Morning yoga overlooking Tuscany is not a bad way to start the day.
The Chef: Massimiliano “Massi” Giovannini
Massi first cooked for us during my birthday celebration, serving a rich Tuscan steak prepared slowly over hot coals. He spent hours stoking the coals before serving this unforgettable meal.
He also led a cooking class that made such an impression that when he and Jordana invited us back for their retreat, I Dream of Tuscany, we didn’t hesitate. If you’re looking for private dinners, cooking classes, or curated food-and-wine experiences, they create the kind of moments that become trip highlights.
Massi, an Italian native, spent time as a sommelier in New York at Del Posto and later worked alongside Michael Chiarello in Napa before returning home to Tuscany, where he now creates unforgettable experiences as a private chef. His wife Jordana—a forager, artist, and herbalist—brings her own creativity and deep connection to the land. Together, they blend food, wine, nature, and hospitality into truly memorable gatherings through their company LOVE WINE AND CHEESE
The Riding: Tuscany by Bike
Our first cycling trip stuck mostly to paved roads, but on the birthday trip we fully embraced the gravel routes Tuscany is famous for. Riding the strade bianche is part challenge, part postcard. Every turn seems to reveal another cypress-lined ridge or medieval village in the distance.
We used Anima Toscana Bike Tours for rentals, guiding, and support, and they were fantastic. Great equipment, smooth logistics, and local knowledge that led us through scenic backroads and charming towns we would have missed on our own.
One day, we even passed Lance Armstrong and George Hincapie on the road and later realized based on their Strava route and Instagram posts that we had stopped at the same coffee shop: Sapori di Radi. Tuscany keeps things interesting. SAPORI DI RADI - Restaurant Reviews, Photos & Phone Number - Tripadvisor
The Wines: Memorable Tuscan Stops
No Tuscany trip is complete without wine, and over three visits we managed to taste more than a few unforgettable bottles and can’t possibly list them all here. But, here were a few of our favorites that stood out from our most recent trips.
Ciacci Piccolomini d’Aragona
We arrived at Ciacci Piccolomini d'Aragona after our longest ride of the birthday trip, dusty and hungry, and were welcomed into a tasting room decorated with vintage bicycles and cycling jerseys. Local snacks, Brunello in the glass, tired legs, happy people—it was perfect timing.
Salicutti
Visiting Salicutti in Montalcino was a highlight. We met the German owner, who seemed to embody the wines themselves: precision, discipline, and total respect for the land. The estate farms three vineyard sites – Teatro, Sorgente, and Piaggione—their three different Brunello di Montalcino that capture the character of each parcel, delivering wines of purity, structure, and a strong sense of place.
Chiappini
In Bolgheri, we visited Giovanni Chiappini Firma - Bolgheri , a warm family-run estate along the famous Via Bolgherese. Giovanni Chiappini built the winery from farming roots, and today his daughters help lead the next chapter.
Bolgheri is famous for a different side of Tuscany—powerful yet polished reds built around Bordeaux varieties like Cabernet Sauvignon, Merlot, and Cabernet Franc. At Chiappini, those coastal influences and family roots come together in wines that are structured, expressive, and unmistakably tied to this special corner of Tuscany.
Villa Calcinaia
One of the most memorable visits of all was Villa Calcinaia , where we were welcomed by the current Count of the Capponi family. The estate has been in family hands since 1524, and that sense of history is impossible to miss. The Capponi family has long combined tradition with innovation; in the 1600s, one of the family’s Counts even wrote an early treatise on winemaking techniques inspired by the French.
Then came the real surprise: a 50-year-old Chianti Classico that was still vibrant, layered, and graceful. A reminder that great Chianti can age with remarkable elegance.
Why It Inspired Our Sonoma Valley Sangiovese
Across these trips, we drank countless wines, including one memorable evening built entirely around 100-point bottles. But what stayed with us was the feeling of Tuscany. The hospitality. The rustic meals. The gravel roads. The long tables. That spirit is what we hoped to capture in a bottle in our 2024 Flight Path Sonoma Valley Sangiovese—California sunshine with a Tuscan heart.
Worthwhile Side Trips
Volpaia
Castello di Volpaia is more than a winery—it’s an entire medieval village woven into the Chianti hills. You can stay overnight, taste wine, enjoy a meal, or even take a cooking class with owner Giovanna in her own kitchen. “Gio” as they call her is a spectacular women. She invented a system to run wine through the town via a “vino ducto” - a system to transport wine under the streets to the various building where their winery operations are housed. Perfect for an overnight or two to enjoy all that their tiny village has to offer. We love this little town so much that we’ve been twice now. You can find Volpaia wine in some restaurants and shops in the US.
Civita di Bagnoregio
A tiny hilltop town reached by a long pedestrian bridge, Civita feels almost unreal. It’s ideal for a short overnight stay. Quiet after dark, but with surprisingly excellent restaurants. We loved dinner at Alma Civita and stayed at AirBnB Casa Piazza San Donato.
