Arrive and settle in your amazing accommodations in Cortona 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. 

Our morning will start leisurely with breakfast at our hotel. After breakfast, we will have a late morning departure and head towards a stunning winery on the Tuscan hills. Here, we will enjoy an amazing wine tasting and full lunch while learning all about the unique wines produced on the property. After lunch, we will head towards the somewhat undiscovered city of Arezzo.

In 2015, the enchanting Tuscan city of Arezzo launched a magical new tradition dedicated entirely to the spirit of Christmas. Known as Arezzo: Città del Natale, this month-long festival has quickly become one of Italy’s most celebrated winter events, welcoming over one million visitors each year from around the world.

During our time in Arezzo, you’ll be immersed in a festive wonderland filled with charming wooden stalls showcasing handcrafted gifts, artisanal decorations, and local treasures. The city comes alive with twinkling lights, traditional rides, an ice-skating rink, and the irresistible aromas of seasonal treats and Tuscan specialties waiting to be tasted.

As you wander through medieval streets transformed for the holidays, you’ll experience the warmth, joy, and timeless beauty that make Arezzo truly unforgettable at Christmastime. From festive sights and sounds to indulgent food and heartfelt traditions, this is more than a visit—it’s a once-in-a-lifetime holiday experience that lingers long after you return home. Simply put, no city compares to Arezzo at Christmas.

The Val d’Orcia area of Tuscany is undoubtedly one of the most breathtaking and picturesque areas in all of Italy—and its magic is even more enchanting during the Christmas season. In the morning, we will visit the lovely village of Pienza.

Visiting Pienza feels like stepping into a perfectly composed Renaissance painting. Perched above the Val d’Orcia, the town offers sweeping countryside views, elegant stone streets, and harmonious architecture shaped by Pope Pius II’s humanist vision. 

After lunch, we will move on to Montepulciano to stroll in its beloved annual mercatino (open-air market).

Featuring more than 80 beautifully curated stalls, the market showcases an exceptional selection of handcrafted gifts, making holiday shopping effortless—even for the most discerning person on your list. Great care is taken to ensure originality and quality, with strong participation from local artisan associations and a rich variety of products spanning fine woodwork, handmade leather goods, and traditional artisanal foods.

Set in the iconic Piazza Grande and the surrounding streets, the market is more than just a shopping experience. As you wander from stall to stall, you’ll also have plenty of opportunities to sample regional specialties, sip seasonal treats, and fully immerse yourself in the festive flavors and timeless beauty of Tuscany at Christmastime.

Always a group favorite, today’s adventure begins deep in the Tuscan forest with an unforgettable truffle hunt led by our dear friend Luigi, a local truffle hunter, and his expertly trained dogs. As we wander through the woods, Luigi will share fascinating legends, traditions, and curiosities surrounding this rare and prized gift of nature—one of Tuscany’s most treasured (and coveted) delicacies.

The experience beautifully unfolds from field to table. After the hunt, we make our way into the kitchen, where you’ll take part in a delicious hands-on cooking class using some of the freshest local ingredients. Savor each course and end on a sweet note with a freshly baked dessert and hot espresso. 

Grab your comfiest shoes, your stretchiest pants, and don’t forget your camera—today we’re setting out on a delightful culinary stroll through Florence! This special daytime foodie walk takes us through the heart of the city to beloved, family-owned shops that have been delighting locals for generations. Along the way, we’ll savor a tempting variety of bites, desserts, and drinks, including seasonal favorites like panforte, the iconic fruity-and-nutty holiday treat, and several irresistible varieties of panettone. Lunch will be a true celebration of the season—fresh, local, and festively Florentine.

Afterward, enjoy a relaxed afternoon at your leisure. This is the perfect time to shop for unique gifts, wander Florence’s historic streets, or step inside one of the city’s stunning churches to soak in the beauty and quiet charm.

Today, you will wander through the medieval heart of Siena as the Christmas market brings the city to life with twinkling lights, festive music, and charming wooden stalls set against centuries-old stone buildings. The air is filled with the scent of roasted chestnuts, sweet pastries, and holiday spices as you explore Piazza del Campo and the surrounding streets at a relaxed pace. Enjoy free time to browse handcrafted gifts, regional food specialties, and seasonal decorations while soaking in the warm, joyful atmosphere that makes Siena especially magical at Christmastime.

In the afternoon, we leave the city behind and journey into the rolling Tuscan countryside for a truly special experience—a wine tasting hosted by our dear friend Vittorio. In an intimate, welcoming setting, Vittorio will introduce you to outstanding local wines and share stories of Tuscan winemaking traditions. The highlight of the visit is a tasting of exceptional Vin Santo, Tuscany’s beloved dessert wine, savored alongside traditional cantucci for the perfect sweet finish to a festive and unforgettable day.

On this day, we will visit the magical hill town of Assisi, a place of extraordinary beauty and deep spiritual significance, especially meaningful during the Christmas season. Assisi is the birthplace of St. Francis, who in 1223 created the world’s first living Nativity, introducing the human reenactment of the Christmas story and forever shaping how the Nativity is celebrated around the world. As we stroll through Assisi’s medieval streets, softly glowing with holiday lights, you’ll feel the timeless serenity that has inspired pilgrims for centuries.

We will then enjoy lunch and an olive oil tasting at one of our favorite frantoio, where you’ll sample remarkable, freshly pressed extra virgin olive oil and learn why Umbrian EVOO is considered among the finest in Italy. Our day concludes in Castiglione del Lago, where we will take in the festive atmosphere and admire the spectacular Christmas tree illuminated on the waters of Lake Trasimeno—an unforgettable and unique holiday experience.

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

NOTE: As we partner with small, family-run businesses, some flexibility in the above itinerary is necessary. We may adjust the schedule, modify activities, or substitute locations to ensure the best possible experience. A finalized itinerary will be provided two weeks before our adventure begins.