The Ultimate Umbria and Tuscany Self Drive Explorer

Welcome to Rome! Upon your arrival at the Rome Airport, you'll collect your rental vehicle and begin your journey north towards Umbria, often referred to as the Green Heart of Italy. Enjoy a scenic drive of approximately 2 1/2 hours to the charming medieval walled town of Perugia. Immerse yourself in the rich history and beauty of this enchanting destination as you settle in for the night in the Perugia area.

Today, explore the captivating hilltop city of Perugia, renowned for its compact historic center and medieval streets. As you wander through its charming alleys, you'll discover a wealth of cultural treasures and architectural wonders. Consider a walking tour of the area or perhaps embarking on a leisurely discovery drive through the picturesque Umbrian villages of Torgiano and Deruta, both celebrated for their timeless beauty.

Embark on a scenic drive of approximately 2 hours into the picturesque region of Tuscany. Your journey will take you through the charming Valdichiana, where you'll have the opportunity to explore the idyllic villages of Cortona, Montepulicano, and Montalcino, each offering its own unique charm and character. Consider indulging in optional activities along the way, such as delightful wine tasting and a cellar visit at Avignonesi. Your journey concludes in Buonconvento, a historic settlement nestled south of Siena at the confluence of the Arbia and Ombrone Rivers. Alternatively, you may choose to stay overnight in nearby Siena, immersing yourself in the vibrant atmosphere of this iconic Tuscan city.

Set out to further explore the captivating Tuscan countryside as you journey to the scenic Val d'Orcia, located just south of San Quirico. As you explore the Val d'Orcia region, you may wish to partake in an optional truffle-hunting excursion. Next, venture onwards to Castiglione, situated on the fringes of the Monte Amiata forests, where you can immerse yourself in the tranquil beauty of the surrounding landscape. After a day filled will exploration and discovery, return to your hotel.

Take a journey through Siena, offering captivating views of the Chianti hills adorned with vineyards, olive groves, and timeless cypress trees that dot the landscape. Consider making a stop at the charming walled village of San Gimignano. After checking into your hotel, take the remainder of the evening to unwind at your leisure, soaking in the ambiance of the Montespertoli area and reflecting on the day's adventures amidst the Tuscan countryside.

Embark on a picturesque drive through the heart of Tuscany and the stunning landscapes of the Chianti countryside. After spending some time in the beauty and heritage of the Chianti region, drive approximately 45 minutes to the enchanting city of Florence. Here, you'll spend the night, ready to explore the cultural treasures and culinary delights of this iconic Italian destination.

We highly recommend either taking an optional sightseeing private tour or explore on your own. If you choose self-guided exploration on foot, start with the awe-inspiring Medici Chapels, the final resting place of the renowned Medici family. Next, venture to the iconic Uffizi Gallery, a treasure trove of priceless Renaissance art. Here, you'll have the opportunity to admire masterpieces by renowned Italian artists such as Botticelli, Leonardo da Vinci, Michelangelo, and Raphael. As the day draws to a close, reflect on the day's adventures and soak in the beauty of the city.