One Unforgettable Week In Florence and Tuscany
Our Fall 2026 Women’s Florence & Tuscany tour wrapped up a few weeks ago and I’m still craving gelato. it was a week of beautiful landscapes, amazing food and wine, and a wonderful group of women who quickly felt like old friends. We even celebrated a birthday and a retirement along with way. Here are just a few memorable moments from the trip.
The medieval wine windows of Florence
On a walking tour, local guide Michele introduced us to some of the city’s hidden gems, like the “wine windows,” tiny centuries-old doors where Florentines once knocked and had wine passed out to them. The windows were originally created as a way for winemakers to bypass taxes and sell directly to the public. And when the plague hit in 1630, they became a useful way to buy and sell wine without coming into contact with another person.
Il Palio in Siena
In Siena, our guide, Luisa, explained the history of the city’s 17 neighborhoods, or contrade, and the fierce rivalries surrounding Il Palio, the legendary bareback horse race held every year in the city’s main square. Suddenly, the flags adorned with elephants, geese, and dragons we saw everywhere made sense.
A day in Montepulciano wine country
From Siena, we set out for a full day in the heart of Tuscany’s wine region. After a stop to explore the charming medieval city of Pienza, we visited a family-owned winery and farm in Montepulciano. There, we enjoyed a wine tasting and lunch made entirely with organic ingredients—from olive oil to pecorino cheese to pasta flour—that they grew and made themselves.
Truffle hunting with Iris
On a beautiful estate that’s been in the same family for six generations, we went truffle hunting with Iris. An adorable and very talented dog, she found 5 black truffles! The 3-course homemade lunch we had afterwards, finishing with biscotti to dip in a glass of the local Vin Santo (“Holy wine”), was a trip favorite.
Great views and gelato in San Gimignano
San Gimignano feels like stepping back in time. A stunning hilltop town, it’s famous for its skyline of medieval towers and postcard-worthy views of the Tuscan countryside. Gelato from Dondoli, voted “Best In the World,” may have happened two or three times during our stay. And of course we had to sample a cone from their competitors just across the piazza—for comparison’s sake.
Pasta making and a special birthday treat
With a view of the towers at sunset, we learned to make pasta at the home of our teacher Francesca. After a delicious al fresco dinner, Francesca surprised the birthday girl in the group with a a crostata, a traditional Tuscan dessert made by her mother. It was such a thoughtful gesture, the kind of personal touch that makes me appreciate the relationships I’ve built with locals over the years.
A huge thank you to the wonderful women who joined me. From great conversations to shared discoveries and lots of laughs, you truly made it a trip to remember. I loved sharing Florence and Tuscany with you!
This is your invitation to join me in Tuscany in 2027
I’m already hard at work on next year’s tour and I can’t to experience it all again, along with a few new surprises. I’ll be leading two trips in 2027, from September 16 – 23 and September 24 – October 1, with a limit of 8 guests on each. The price is $4,985 per person (and worth every penny!).
If Tuscany has been on your list, now’s the time! Check out the full tour details, fill out the interest form on our 2027 tour page, and get ready for the experience of a lifetime!
Arrivederci for now!
Janet