One Week, 7 Women–Pasta, Truffles and Wine!
I’ve been home from the women’s Florence & Tuscany Tour for a month now, but my mind frequently wanders back to that very special week. First, the six women who signed up for the tour were wonderful–curious, adventurous, interested in learning and interacting with local people–in short, exactly the kind of travelers I’d hoped One Street Over would attract!

First stop, Florence
Our week began in Florence at the elegant Hotel Orto De’Medici, so named because it was in the hotel garden that a 14-year old aspiring sculptor named Michelangelo first met Lorenzo de’Medici in 1489. On our first afternoon we joined a local guide for an introductory walking tour of the city, taking in the magnificent pastel-colored Duomo that always leaves me awestruck even though I’ve seen it many times. After the tour we walked to a restaurant just a couple of blocks away for a welcome dinner with wine. The night ended several hours later with our group the only remaining guests, and the very friendly staff insisting that we all sample the limoncello on the house. It was a great way to start the trip!



Art and cocktails, anyone?
The next morning after breakfast we took a short walk to the Uffizi Museum to meet our guide Marco. It would be an understatement to say that Marco knows a lot about Renaissance art. Visiting the museum with an expert who shared some fascinating stories behind the art–like female Renaissance artist Artemisia Gentileschi’s gruesome painting of the biblical story of Judith beheading Holofernes, where she gave the dying Holofernes the face of the man who had raped her. After our tour, some guests continued walking and crossed the Ponte Vecchio to visit the Boboli Gardens, while a couple of us went to the Uffizi’s rooftop café for an Aperol Spritz.
On to Siena
The next day we were off to Siena, stopping on the way to take in the magnificent view of Florence from the hilltop Piazzale Michelangelo. Once settled in to our hotel, just outside the historic city walls, we walked into town for an al fresco group lunch. In the afternoon we met our local guide for a walking tour that took us through the winding medieval alleys still decorated with flags and banners from the recent Il Palio horse race. We ended our tour at Siena Cathedral, whose striped pink and green marble remind me of licorice allsorts candy. Inside are sculptures by Bernini and Michelangelo, a library of Medieval illuminated manuscripts, and most impressive, its mosaic floor with 56 inlaid panels made by leading artists between the 14th and 19th century.



Our first dinner in Siena was at the Michelin-recommended Osteria le Logge, where we sat outside at a candlelit table, all of us dining on the 4-course Chef’s Tasting Menu, which ended with a quartet of hazelnut-based desserts. Delicious, and a truly magical night!
Wine, and more wine
Day four of our trip took us on an all-day excursion to the nearby wine region of Montalcino, where Italy’s famous Brunello wines are produced. Our driver Enrico took us first to Molino Di Sant’Antimo Winery, a woman-run operation where the grape harvest was in full swing. After a tour of the cellar and bottling area we walked up to the estate for our tasting, sitting outdoors with a postcard-perfect view of the vineyards. Our next stop was the Abbey of Sant’Antimo, an out-of-the-way Romanesque chapel set in a peaceful olive grove. At our next winery, we had a farmhouse lunch of antipasto and gnocchi to go with our three wines, a sparkling, a white, and a red. Before driving to our third and final winery, we stopped to walk around and browse the shops of Montalcino village, set in the midst of stunning Val d’Orcia Natural Park. Next, we visited a family-owned farm and winery, in operation since the 1600s, where the group favorite was the Brunello di Montalcino Riserva DOCG. We returned to Siena that night pleasantly sated.



Pasta Making Nonna’s Way
The following morning we made the trek to an 1800s farmhouse so far off-the-beaten-path that our driver needed GPS coordinates to find it. But it was more than worth the trip! We were greeted by our host, Guilia, along with her two cats, one dog, her baby William, and his babysitter. Guilia and her husband undertook the renovation of the farmhouse as a labor of love, moving in before it had electricity and running water, and clearing the land themselves. They now have an olive grove with hundreds of trees, a small vineyard where they make their own wine for friends and neighbors, a vegetable garden, chickens, and goats, from which they get milk to make cheese and “goat-accino” coffees (surprisingly sweet, and non-goat flavored!).
Guilia is a force of nature, a cooking instructor with all the charisma and personality of that other Julia, and who should definitely have her own cooking show. She instructed us in the proper way to make pasta, using only flour (hand ground by her neighbor) and eggs from her chickens. As we rolled and hand cut our tagliatelle with varying degrees of success, Guilia regaled us with stories of her nonna (in perfect English) and offered encouragement–”bellissima!” Spending time with Guilia in her beautiful rustic kitchen, eating her homemade foccacia and ricotta along with our misshapen pasta in a sauce she whipped up with tomatoes and basil from her garden, was one of the highlights of the week.



Hunting For Truffles
On day 6 our driver picked us up in the morning and brought us to San Miniato for our truffle hunt. We arrived at a stunning 17th century villa, its grand rooms adorned with beautiful antiques, oil paintings, and wild boar taxidermy. We were greeted by professional truffle hunter Francesca, whose family has lived in the villa for 6 generations. She led us out to the kennel where we were introduced to Iris, who we were warned was only 9 months in to the 2 years of training it takes to become a truffle hunter, and might not find any truffles. Iris was very enthusiastic, however, and proved her handler wrong by finding two black truffles and a more rare (and expensive) white truffle! After traipsing through the woods, we were hungry and sat down in the elegant dining room for a 3-course lunch, starting with the best scrambled eggs I’ve ever tasted, attributed to the shaved truffles on top. We had bread with truffle oil and pasta with truffles and finished with homemade biscotti and a glass of Vin Santo (Holy Wine) to dip it in. A perfect meal to cap off a wonderful day!



Last stop, San Gimignano
From San Miniato, we drove to our final destination for the week, the quintessential Tuscan town of San Gimignano. If you’ve looked at a Tuscany guidebook, you’ve no doubt seen a photo of San Gimignano’s unique “skyline,” with its 13 medieval stone towers that can be spotted from miles away. We checked into our hotel, a place that has operated since 1100(!), originally as a way station for pilgrims traveling south to Rome. Hotel La Cisterna is in a prime location in San Gimignano’s central piazza, from which the city’s streets branch out like wheel spokes, so that everything is within easy walking distance. The hotel itself has simple, unfussy rooms and an elevator that can accommodate one person + suitcase, or two people with carryons, but the VIEW! All of our bedrooms had terraces that overlooked either the bustling piazza or the rolling hills of the Tuscan countryside or–in the case of the top floor Tower Room–both! The views were truly spectacular and we all gathered in the Tower Room on our last night for a champagne toast while we watched the panoramic sunset.



On the last day of our tour we joined a local guide for a walk through San Gimignano in the morning, then enjoyed some free time to shop for artisan-made leather bags, linen shirts, printed textiles, and olive wood, all specialties of the region. In the afternoon we hiked up a steep hill to the attend a wine school masterclass focused on the white Vernaccia grape, a native varietal that has been grown in this tiny region for 700 years. We sampled three white wines from local vineyards, learning to taste the subtle difference between the newer and more aged bottles. After class, we took the last of our wine and some snacks outside to relax on a shaded terrace with an amazing view of the rolling hills and vineyards lined with tall cypress trees.
After our sunset Champagne party, we walked to a nearby restaurant for a farewell dinner, one of the best of the trip–pappardelle with cinghiale (wild boar) for some, Guinea fowl stuffed with pancetta and donkey milk cheese for others (don’t knock donkey cheese ’til you’ve tried it!), plenty of wine, and tiramisù to cap it all off. It was the perfect end to a fantastic week!
Interesting in joining next year’s tour? Learn more here.



