What happens when you gather a group of extraordinary women in the heart of Italy, and mix in art, wine, pasta, and laughter? You get one unforgettable week in Florence and Tuscany. Our latest women’s small group tour was just that—a perfect blend of sightseeing, cultural experiences, incredible food and wine, and time to relax and enjoy the natural beauty of the region.
Here’s a recap of what we got up to:
Day 1: Ciao, Firenze!
We landed in Florence and checked into a 4-star boutique hotel in the city center. After group introductions, we hit the cobblestones for a walking tour with a local guide who showed us Florence’s must-sees and pointed out some hidden gems along the way. Did you know that Florence has over 250 wine windows, preserved since the 16th century, and many are still operating?
Day 2: Best of Botticelli
Florence is synonymous with Renaissance art, and began our day with a guided tour of the Uffizi Gallery (the world’s first “art gallery”). Standing face-to-face with Botticelli’s Birth of Venus and seeing Caravaggio’s dramatic works close up was an experience that moved some to tears. Our art expert Marco made the art come to life—sharing the juicy backstories behind the masterpieces.
Day 3: Siena Charm
After breakfast, we traded Florence for Siena, driving through the rolling vineyards of Tuscany. Our hotel near Siena’s medieval walls was as charming as the city itself. We learned about the famous Il Palio horse race and the rivalry between Siena’s 17 contrades, (neighborhoods represented by an animal or symbol. I’m partial to the snail.). Our local guide then led us through into the awe-inspiring Siena Cathedral, with sculptures by Michelangelo and Donatello almost get lost amid the baroque splendor. We capped off the night with a 4-course al fresco dinner at a Michelin-recommended restaurant.
Day 4: Chianti and More Chianti
This day was for wine lovers, with a full-day tour of Chianti’s stunning vineyards. We started at the stunning Brolio Castle for a taste of history (and Chianti Classico) before moving on to a vineyard lunch in a setting that felt like a Tuscan dream. We had some free time to stroll the medieval streets of Radda in Chianti, then the afternoon brought us to yet another winery where we sipped and swirled while learning the ins and outs of traditional winemaking.
Day 5: San Gimignano Magic
We arrived in San Gimignano—aka Tuscany’s medieval Manhattan thanks to its many towers—and settled into a centuries-old hotel with views to die for. Free time meant shopping for leather goods, linen, or jewelry (plus an obligatory stop at Gelateria Dondoli for the world’s best gelato). That evening, we rolled up our sleeves for a pasta-making class with a sunset view of the city “skyline,” where laughter, flour, and wine flowed in equal measure.
Day 6: Truffle Time
One of the highlights of the trip was our truffle hunting adventure at a beautiful family estate in San Miniato. With guide Francesca and her trusty truffle dog, Levante, we tromped into the woods and struck culinary gold (three black and one prized white truffle!). Our reward? A three-course truffle feast paired with wine. Back in San Gimignano, we capped the day with a delicious dinner of Bistecca alla Fiorentina, a 2 kilo steak shared by the table.
Day 7: Farewell with Vernaccia
On our last full day, we lingered in San Gimignano for a relaxed morning before heading to a panoramic viewpoint for a wine tasting class featuring the region’s signature white wine, Vernaccia. With rolling hills, olive trees, and vineyards stretched out before us, it was the perfect end to an incredible week. That night we shared one last dinner together and raised a toast to our Tuscan adventure!
Trips like this are why I love what I do. The scenery was stunning, the food and wine amazing, but it was the women who joined me—sharing stories, laughter, and a sense of adventure—that made the week so special. I’m already looking forward to next year’s trip!
Sign ups are open for our 2026 women’s tour. There are four spots left, so don’t wait! Find all the details here.