Montepulciano, Tuscany, Italy, December 2019: Christmas Market in Montepulciano, Piazza Grande, the main square of Montepulciano during the Christmas time.

Christmastime in Tuscany

December 3 - 10, 2023

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 – Hotel L’Orologio 
  • 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, Cortona, Montepulciano.
  • Day Trip and Market Visit in Val D’Orcia, Tuscany’s most photographed area.
  • Two private culinary lessons with Tuscan instructors. 
  • Private foodie tour 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 (Appox. 150 USD or Euros for the week).  
  • Travel Insurance: As of 2023, 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 + Hands-on Culinary Experience

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.

We will have to work for our dinner tonight as we head towards our first cooking class of the week. Roll up you sleeves and grab an apron, as for dinner, you’ll enjoy what you make during class!

Day 4 - Truffle Hunting Experience & Santa Croce Market

Of all the Christmas markets in Tuscany, perhaps the best known and largest is the traditional German market! Located in Piazza Santa Croce, this market has been an annual Florentine tradition for over 500 years! We will stroll through the festive open air stalls and browse for Italian and German goods, both the edible and non-edible kind! When it comes to food, enjoy a bratwurst and salted pretzel along with a cup of mulled wine. Crepes and waffles aren’t too far away either. But if you want to stick with Italian treats, fear not, Italian cheeses, jams and chocolates have been added. This market is the perfect stop for all your Christmas gifts. Today, we will find vendors selling souvenirs, candles, linens, ceramics, hand-knitted sweaters and scarves and gloves to keep you warm! Check out the video below of this breathtaking market.

But before the Santa Croce Market, we visit Certaldo​ for a fun hands-on culinary experience. If the weather permits, we will hunt for truffles with Ricciolo, the fun loving, truffle hunting Lagotto Romagnolo. After out hunt, we head towards the kitchen and cook a delicious truffle-themed lunch with Giuseppina, our instructor and shop owner. This is going to be a delicious experience that is sure to leave lasting memories!

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 - Day trip to Chianti to Visit Wineries + Shopping for Local Products

Spanning the hilly lands between Florence and Siena, this picture-perfect area of Tuscany is filled with landscape, vineyards and artisanal products. Composed of several smaller towns, the Chianti area is most known for its namesake wine and no other area in Italy can offer such beautifully picturesque panorama as this area does. Miles and miles of vineyards adorn the roads, producing some of Italy’s best wines, some estimate upwards of 35 million bottles per year!

We will spend an entire day in the Chianti area, sampling wines, eating local specialties and stopping for Instagram-worthy shots. Today, we explore this area in depth and pay a tribute to the famous foods that come from this area, such as the famous wine, oils and truffles.  We visit my personal friends, as we experience a day filled with food, wine, cooking, laughing and yes, some opportunity to shop.

We will spend the evening in Florence and be present for the official tree lighting ceremony!

Day 7 - Day Trip to Siena for Shopping + Visit to Local Market

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.

In the afternoon, we head back to Florence for some time on your own to spend as you like, before enjoying a group dinner during our final night together.

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
$4,800 USD Per Person for Double Occupancy / Single Supplement is $700 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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