Christmastime in Tuscany

December 1 - 8, 2024

The focus of this magical week will be immersing ourselves in the holiday spirit in one of the world’s most beautiful cities. We will spend time visiting various Tuscan markets, shop for artisanal products and purchase unique gifts not found anywhere else in the world. Skip commercial shops, “early bird discounts” and mass-produced items this year and shop directly from the makers and artisans themselves. Purchase unique hand-made leather goods, wooden gifts, hand-knitted scarfs, pottery, even foodie gifts, all to take back to the States. Our week will also include seasonal cooking classes, and wine tastings, and a delicious street food tour.

Our home base for the entire week will be Florence. Arguably, one of the most historic and most visited cities in Italy, if not the world. Florence is home to such treasures as the Duomo, the Uffizi Gallery, the Accademia, and countless churches including Santa Maria Novella and Santa Croce. Not to be missed is the Ponte Vecchio, or the “old bridge,” the only bridge to cross Florence until 1218 and the only bridge in Florence that was not to be destroyed during WWII. See the bridge illuminated and like you’ve never seen it before! 

Folks should plan on arriving and departing from Florence International Airport.


  • 7 nights 4* accommodations in highly rated, centrally located hotel in Florence.
  • Daily breakfast at the hotel
  • Most lunches, 3 dinners with wine.
  • Lunch on winery 
  • Truffle-hunting in the woods, with truffle themed cooking class and lunch afterwards.
  • Visits to Siena, Chianti, Certaldo, Arezzo, Montepulciano
  • Day trip and market visits with time to shop on your own.
  • A private culinary lesson with Tuscan instructor. 
  • Private foodie tour of Florence with ample samples throughout the walk .​
  • Time on your own for shopping!
  • Market visits throughout the week 
  • ​Private transportation throughout the week 
  • Fully guided and escorted by Francesca, native Italian, fluent in the language and Italian customs.


  • Airfare / Flights (Folks should fly into Florence Airport). 
  • Transfer from / to airport
  • ​Tips / gratuities for guides, instructors and drivers 
  • Travel Insurance: We will require everyone traveling with us to carry some form of Travel Insurance. Click here for info.  

Day 1 - Check-in Hotel + Welcome Feast at Local Restaurant

Arrive and settle in your accommodations in the early afternoon. Unpack and make yourself at home knowing you will not need to repack until your departure. Enjoy the nearby sights of our home for the week, stretch your legs in the nearby shops or grab your first Christmas treat. 

In the evening, we will meet for our first group activity. We will enjoy a welcome wine tasting and dinner with our fellow travelers and new friends. The week’s activities will be discussed during our welcome dinner. 

Day 2 - Visit to Arezzo, the City Of Christmas

In 2015, a new initiative in Arezzo began focusing solely on Christmas. Called Arezzo: Citta Del Natale, the month long festival draws in well over a million visitors, all here to see, taste and experience this extraordinary city. Attractions include stalls selling handmade crafts, rides, ice skating and so much more. We will spend the entire day here, browsing the stalls and enjoying all this city has to offer, including delicious food! This is a once-in-a lifetime experience that is sure to leave an impression on your soul. No city compares to Arezzo at Christmastime.

Day 3 - Visit to the Mercatino di Natale Mentepulciano

The Val D’Orcia area in Tuscany is undoubtably one of the most beautiful and picturesque area in all of Italy. That beauty comes to live that much more at Christmastime. With more than 80 stalls, the now annual mercatino (open air market) offers handmade gifts to make shopping for even the pickiest person in your life a breeze! Great attention has been paid to the originality of the products sold at the market, with the involvement of the artisans associations and the presence of diversified products in categories such as wood, leather and artisanal foods.  Located in Piazza Grande and its vicinity, the market not only offers gifts for everyone, we will have plenty of opportunity to taste specialty foods along the way.

Day 4 - Truffle Hunting Experience & Special Opera Dinner

Always a group favorite, our journey today begins with a unique truffle hunt in the forest with trained dogs, and with our dear friend Luigi, a local truffle hunter. Luigi will tell us interesting legends and curiosities about this precious (and expensive) gift of nature. The experience will start in the fields and will end in the kitchen, where you will sit down to enjoy a full meal, sample the truffles, and finish with Tuscany’s best panna cotta.

In the afternoon, we walk off our hearty lunch in San Gimignano. Shop at the small, specialty shops for unique gifts such as Tuscan leather, shoes, handbags, or some delicious Tuscan wine to bring back and enjoy over your Christmas dinner.

Dinner tonight promises to be a once-in-a-lifetime experience. Meet our friend Lucrezia in her home for a magical dinner that will include not only amazing foods, but our own private opera concert!

Day 5 - Foodie Walking Tour with Seasonal Samples

Grab your comfy shoes, stretchy pants and camera because today, we’re hitting the town for a special kind of walk! During the day, we will enjoy a delicious foodie walk along some of Florence’s beloved family-owned shops. We will sample delicious foods, desserts and drinks including the seasonal Panforte, a delicious fruity and nutty holiday treat and various kinds of panettone. ​Lunch is sure to be seasonal, local and festive!

Enjoy some time on your own this afternoon to shop, sightsee or visit some of the local beautiful churches. In the evening,  we will meet for dinner and enjoy a scenic nighttime walk under the Christmas lights of Florence.

Day 6 - Hands-On Cooking Class + Afternoon Visit to Siena

Roll up your sleeves, grab your apron and let’s get cooking!

In the morning we will visit our dear friend Rosanna in her private home for a hands-on 3 course cooking class. Enjoy the preparation of seasonal dishes like pumpkin ravioli, herbed chicken and what would a delicious Tuscan meal be without dessert! Will it be chocolate salami, or perhaps panforte! Either way, you’re sure not to leave her house hungry!

After our cooking class, we will enjoy a visit to Siena for some guided time with our trusted guide, plus time on your own to shop around. Made famous for its horse-race known as the Palio, Siena is a not to be missed medieval city in central Tuscany. The shell-shaped Piazzo del Campo is perhaps its main attractions and where the Palio takes place, although today, we’re here to hit the markets in one of the biggest medieval squares in the world. Filled with many churches and cathedrals, the Duomo, the largest church in Siena, is adorned for the season. We will have ample time to walk about the square and pick up a few souvenirs. May we recommend some foodie gifts? Perhaps Ricciarelli, a typical Sienese biscuit made with almond paste, or the season Panforte, a fruit cake still made according to a Medieval recipe.

Day 7 - Time on Your Own + Full Tuscan Dinner

Our week together is winding down and by this point, you might be getting tired. So today you get to enjoy sleeping in and some time on your own in the beautiful city of Florence. Visit the Santa Croce Market, enjoy some street food and grab a few last minute gifts. Or perhaps high-end shopping is your thing? Not to worry. Head towards Via Tornabuoni for all your brandname gifts.

We will gather together again as a group for a full Tuscan dinner, with lots of wine, of course!

Day 8 - Arrivederci!

Our week of food, wine and shopping is winding down. The tour ends after breakfast at the hotel.

Price & Details

​8 Days / 7 Nights
$5,100 USD Per Person for Double Occupancy / Single Supplement is $1,000 USD. (See details above for list of inclusions / exclusions.)
$1,000 USD Non-refundable Deposit is required to secure your spot.

Francesca Montillo, Native Italian, Owner and Tour Leader Accompanies all Activities​​. Contact Francesca at for booking/reservation and further details.

If you would like to reserve a spot for this tour, or have any questions, please use the contact form below and we will send you the necessary booking instructions or additional information.

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