Incredible Umbria & Tuscany

Arrival in Umbria – Welcome to the Green Heart of Italy

Welcome to Umbria, a region of rolling hills, ancient towns, and unforgettable charm. Upon arrival, your private driver transfers you to your hotel for check-in.

The rest of the day is yours to unwind and settle in. Relax after the journey or take a gentle stroll to soak in the peaceful atmosphere of this beautiful region.

Assisi City Tour & Trip to Gubbio – Medieval Magic in Umbria

After breakfast, meet your guide and set off on a walking tour of Assisi, often described as the cradle of Romanesque art. Explore the UNESCO-listed Basilica of San Francesco, where masterpieces by the greatest artists of the Middle Ages bring the story of St. Francis to life. As you wander through Assisi’s quiet streets and Franciscan sites, you’ll feel as though you’ve stepped back into the medieval world.

After a break for lunch, continue to Gubbio, a beautifully preserved town set dramatically on the slopes of Mount Ingino. Here you’ll discover the striking Piazza Grande, framed by imposing public palaces, and visit the Palazzo dei Consoli, a Gothic masterpiece completed around 1340. You’ll also see the Palazzo del Podestà, now the Town Hall, and the evocative ruins of the Roman amphitheatre.

At the end of this immersive journey through Umbria’s medieval gems, you return to your hotel in Assisi for a relaxing evening.

Exploring Umbria Countryside – A Journey Through History

In the morning, meet your driver in the hotel lobby and set off on an exciting tour through Umbria’s enchanting countryside.

First, visit the medieval fortress city of Spoleto, where a private guide will take you on a fascinating walk through the town. Explore its Roman temples, theatres, and arches, stepping into centuries of history.

Next, head to Bevagna, a charming town with half a dozen medieval churches, two Roman temples, and the remains of an ancient Roman theatre, offering a glimpse into its rich heritage.

Your journey continues to Spello, where the town’s Roman origins are beautifully reflected in its stone gates and ancient walls that surround this picturesque village.

After this immersive exploration of Umbria’s treasures, you’re driven back to Assisi, where the rest of your day is free to enjoy at leisure.

Arrival in Montepulciano

Upon arrival, check in to your hotel and enjoy a well-deserved rest in one of Tuscany’s most atmospheric towns.

Tour to Cheese Farm and Winery – Flavors of Val d’Orcia & Tuscany

This morning brings another unforgettable experience as you set off to discover the culinary treasures of Pienza and Montepulciano.

Your driver takes you through the rolling Tuscan countryside to Pienza, world-renowned for its Pecorino di Pienza — a delicious sheep’s-milk cheese whose name comes from pecora, meaning “sheep.” Start with free time to explore Pienza’s UNESCO-listed historic center, admiring Palazzo Piccolomini, the beautiful Cathedral of Pienza, and Palazzo Comunale.

Then continue to a picturesque organic cheese farm perched on a hill overlooking the entire Val d’Orcia. Here, a local producer walks you through every stage of pecorino production, from fresh and soft to aged and complex. It’s an intimate look into one of Tuscany’s most beloved traditions.

Your journey continues at a traditional winery near Montepulciano, where you enjoy a tasting of the celebrated Vino Nobile di Montepulciano — one of Italy’s most prestigious DOCG wines and an icon of Tuscan winemaking.

After the tasting, enjoy some free time to wander the historic center of Montepulciano before returning to your hotel for a relaxing evening.

Cooking Class in Montalcino – A Day of Tuscan Flavors & Noble Wines

Following breakfast, your private driver picks you up and whisks you away to Montalcino, the ancient hilltop village celebrated worldwide for its Brunello di Montalcino — a powerful red wine crafted from Sangiovese Grosso grapes.

A few kilometers outside the village, you arrive at a charming farm restaurant, where your hands-on cooking adventure begins. Start by gathering fresh ingredients straight from the garden — vegetables, herbs, even eggs — before diving into a lively workshop focused on creating a traditional Italian meal. Over the next three hours, you’ll learn authentic techniques, discover local dining traditions, and prepare a full Tuscan feast.
Your efforts are rewarded with a leisurely lunch featuring appetizers, homemade fresh pasta with sauce, a hearty main course, and a sweet dessert.

The experience continues with a private visit to a winery set inside a historic castle. Wander through the cellars and vineyards, enjoy sweeping views of the countryside, and taste prestigious wines including Brunello “Riserva” and Rosso di Montalcino.

After this enriching day of flavor and tradition, your driver returns you to your hotel, where the evening is yours to enjoy.

Departure from Montepulciano – Medieval Treasures, Timeless Towers & Your Journey to Florence

This morning, you say goodbye to Montepulciano and begin a day filled with beauty, history, and unforgettable Tuscan landscapes. After check-out, your private driver welcomes you and sets off toward one of Italy’s most captivating medieval treasures—Siena.

Your journey begins with a 3-hour walking tour led by a passionate local guide. In Siena, every step reveals centuries of artistry and tradition. You explore the breathtaking Cathedral of the Duomo, home to masterpieces by Nicola Pisano, Ghirlandaio, Ghiberti, Donatello, and Jacopo della Quercia. Then you step into the heart of the city, Piazza del Campo, whose elegant, shell-shaped form has hosted Siena’s legendary horse races for generations. It’s a place that feels frozen in time—yet full of life.

Your Tuscan story continues in San Gimignano, where you have free time to wander at your own pace. Rising proudly above the rolling countryside, the town’s 14 medieval towers create one of the most iconic skylines in Italy. Explore its peaceful piazzas—Cisterna, Duomo, Pecori, and Erbe—each with its own charm, its own rhythm, its own moment of magic. Whether you linger inside ancient churches or simply savour the views, San Gimignano never fails to inspire.

After this day, rich with culture and emotion, you continue your scenic journey to Florence.

Arrival in Florence

Welcome to Florence—the birthplace of the Renaissance. Upon arrival, your private driver brings you to your hotel for check-in. The rest of the day is yours to unwind, reflect on today’s discoveries, and prepare for the unforgettable experiences Florence has in store

Florence Sightseeing – Art, Elegance & Renaissance Icons

Meet your private guide and dive into Florence’s greatest hits. Begin in Piazza del Duomo and step inside the Baptistery of St. John, a jewel of medieval artistry. Continue toward Piazza della Repubblica, strolling past the elegant Strozzi Palace and the stylish boutiques of via Tornabuoni.

Next up — the legendary Galleria dell’Accademia. Nothing prepares you for the moment you stand before Michelangelo’s David. A masterpiece in every sense. The tour ends at the iconic Ponte Vecchio, where riverside views and charming shops set the mood for the perfect Florentine afternoon.

Evening? Yours to enjoy — maybe a glass of Chianti or some handmade gelato.

Departure – Until Next Time, Italy!

This is the final day of your unforgettable Italy adventure. After checking out of your hotel in Florence, your private driver will transfer you to the airport for your flight home. We wish you a safe and pleasant journey, and we look forward to helping you plan your next incredible vacation!