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The Best Tuscan Guided Tours in Winter

These top guided tours will transform your winter vacation in Tuscany into a treasured memory, adding fun and classical sites and experiences and just the right about of adventure to your itinerary. All of these quality guided tours are featured in the winter months and are lead by expert guides trained in culture, art, and history.

Choose from half day or full day tours where you can appreciate the unique (and delicious) culture in Tuscany even when the weather outside is brisk, windy and uninviting. Or book one of the tours that will take you on an urban adventure, exploring the monuments, museums, and sites of the city like Pisa and Lucca, to be seen any time of the year. Some of our favorites include a combination of the sites, the landscapes, and the delicious food all with private transport and an English speaking guide.

» Don' t forget to check out the top 5 activities we recommend in Winter

Cooking Classes & Fun Winter Tours in Tuscany

1. Stay Warm in the Kitchen

When the weather outside is telling you to stay inside, then the only thing to do is cook yourself up a plate of homemade pasta. These three tours feature the culinary delights of Tuscany in the San Gimignano countryside, the Florentine legendary Castello del Trebbio in the hills of Florence or the totally unique street food from Livorno.

- Join your chef in making homemade pasta and sauce while learning about the intricacies of producing Tuscan wine surrounded by the landscape of the famous Tuscan tower town, San Gimignano.

- Could anything be more romantic than visiting a private Tuscan castle and with a glass of wine in one hand and the perfume great Tuscany food in the background? 

- Livorno is will surprise you with its amazing city landscape and absolutely delicious street food. One-of-a-kind throughout all of Italy, the Medici fortress, the canal "roads", and the yummy ponce will have you falling in love with this seaside town that is often off the beaten track of most visitors to Tuscany.

2. Enchanting Vineyards

One of the more famous landscapes of Tuscany falls in the Orcia Valley where you will find the amazing Brunello wine, the creamy Pienza pecorino cheeses, and UNESCO World Heritage Site. Let someone else do the driving while you do the taste testing, especially in Chianti. 

- If you have just one day to explore the countryside of Tuscany, be sure you include this three cities: Siena, San Gimignano, and Monteriggioni which are in Chianti and close to Florence. We choose this tour because it adds a delicious wine tasting to compliment the amazing scenery, make sure to read our review too since we did it!

- Only have a half-day to see and taste the best of Chianti? This tour is perfect. The private transport will take you through the stunning landscape to Castellina in Chianti, a fortified hilltop village of Etruscan origin and then stop at a hilltop castle for a wine tasting. 

- This tour gives you a peek inside the Siena Palio culture, the thrilling event which has taken place for 100’s of years, then it shows of the medieval tower town, a fabulous wine tasting before one last stop at the famous town of Greve in Chianti, where the Gallo Nero stands proud. 

- Maybe it’s not all about the landscape... maybe it’s about the thermal water spas and a glass of Tuscan wine. This tour includes spa time, a massage and a wine tasting in one of the most exclusive wine areas of Tuscany, Montepulciano.

Visiting Vineyards in the Winter & more fun winter tours in Tuscany

3. Keep it in the Family

Our last two tours are for families traveling with kids looking for a way to make these historic cities pop! Two guided tours designed especially for entertaining the younger members.

- Who hasn’t heard of the Leaning Tower of Pisa? And what an impression it makes when you see it tilted to one side up close and in person. This tour will have you skipping the line to get a close-up look and make the experience unforgettable for the kids. Remember though that only kids over 8 can actually climb the tower.

- Lucca is loaded with mystery, just what you need to capture the attention of the kids. A specially organized tour has you stepping back in time to the enchanting Middle Ages where you will explore the hidden corners of this amazing walled town. And of course, can you say no to the best gelato in town?

Our very own DiscoverTuscany family exploring Pisa; in the photo above, the newly opened walkway along the walls that surround most of Pisa from which you can enjoy a great view of Piazza dei Miracoli.

Author: Donna Scharnagl

It has been more than 25 years since I took my first steps in Italy and I still haven’t found a good reason to leave.  Between the food, the culture, the history, the art, the landscapes … did I mention the food? I have become a lifelong student. It didn't take long to learn that Italians all have stories that long to be told; stories that paint a picture of how hard work produces character, how life is made of ups and downs and how good it feels to laugh.


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