Women’s Florence & Tuscany Small Group Tour

September 23–30, 2026
$4,985 per person/dbl occ.

Only 3 spaces left!

Limited to 8 guests
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$250 deposit required

What’s Included

Full-time tour leader

All ground transportation

7 nights in boutique hotels – Florence (2) Siena (2) San Gimignano (3)

All breakfasts; 5 dinners & 3 lunches, including wine

3 winery visits and tastings

1 wine-tasting class

3 tours with local guides

Pasta making class

Truffle hunt

All tickets & admission fees

All gratuities

*Airfare is not included but we are happy to assist in booking your flights

Florence & Tuscany Tour Itinerary

DAY 1 – Arrive in Florence and transfer to your hotel in the city center. Your tour leader will meet the group in the afternoon for introductions, followed by a walking tour with a local guide. We’ll see the iconic Santa Maria del Fiore Cathedral, Piazza del Duomo, and Ponte Vecchio along with some hidden gems. Tonight, we’ll dine together at a favorite local trattoria. (included meals: Dinner; overnight: Florence 1 of 2)

DAY 2 – After breakfast, we meet a local art expert for a guided tour of the Renaissance masterpieces in Florence’s Uffizi Museum. We’ll see and learn about some famous and lesser-known works by Botticelli, Michelangelo, Leonardo da Vinci, and Caravaggio. After, head to the Uffizi’s rooftop restaurant for an Aperol Spritz, and enjoy a free afternoon to wander, shop, or explore the Pitti Palace, Boboli Gardens, and other sights on your own. Dine on your own tonight at one of the many excellent restaurants within walking distance of our hotel. (included meals: Breakfast; overnight: Florence 2 of 2)

DAY 3 – Our driver picks the group up in the morning for the one-hour drive to Siena. On the way, we’ll pass through the beautiful vineyards of Chianti before arriving at our next hotel, located inside Siena’s historic city walls. We’ll lunch al fresco as a group before meeting our local guide for a walking tour, including a look at Siena Cathedral, one of the most impressive works of Romanesque architecture in Italy. We’ll return to the hotel before heading out to dinner at a Michelin-recommended restaurant for an unforgettable meal. (included meals: Breakfast, Lunch, Dinner; overnight: Siena 1 of 2)

DAY 4 – Today we travel to the famous Chianti region for a full day tour. Our first stop is at the impressive 12th century Brolio Castle, home of the first vineyard to produce Chianti. We’ll visit the impressive gardens before enjoying a tasting of Chianti Classico in the Castle cellars. Next, we’ll stop at a Chianti estate for a traditional Tuscan lunch accompanied by a tasting of the farm’s wines. At our third and final winery of the day, the local producer will show us around the estate and cellars. We’ll learn about the traditional Chianti wine making techniques and we’ll sit down to savor a glass of the farm’s renowned wines before heading back to Siena for the night.  (included meals: Breakfast, Lunch; overnight: Siena 2 of 2)

DAY 5 –
After breakfast, we’ll be on our way to our next destination, picturesque San Gimignano, where we’ll stay in a centuries-old hotel with breathtaking views. You’ll have free time to visit the local shops selling leather goods, jewelry, and linen. Be sure to try the gelato at Dondoli, named “Best Gelato in the World,” and located in the piazza near our hotel. In the evening, we’ll sip an apertif while we learn to make hand-rolled pasta at a local cooking class, then dine on our creations, accompanied by charcuterie. (included meals: Breakfast, Dinner; overnight: San Gimignano 1 of 3

DAY 6 – Today we travel to a beautiful estate in San Miniato that has been inhabited by same family for 6 generations. We’ll have a coffee before we meet our specially-trained truffle dog (and handler), and head off into the woods on a truffle hunting expedition. Afterwards, we’ll enjoy a 3-course lunch–featuring truffles, of course!–along with local wine before returning to San Gimignano. Tonight we’ll dine as a group at a favorite local restaurant. (included meals: Breakfast, Lunch, Dinner; overnight: San Gimignano 2 of 3)

DAY 7 –
After a free morning in San Gimignano, we’ll venture just outside the city to visit an organic wine producer in Pancole, where we’ll taste two whites and two reds along with some local cheeses and cured meat. This evening we’ll gather for our farewell dinner at a wonderful restaurant within walking distance of our hotel. (included meals: Breakfast, Lunch, Dinner; overnight: San Gimignano 3 of 3)

DAY 8 – After breakfast, we’ll say arrivederci to Italy and the new friends we’ve made before transferring to the Florence Airport for flights home. (included meals: Breakfast)

Download a printable PDF about our 2026 Women’s Florence & Tuscany Tour