A picturesque 3-day road trip through the heart of Tuscany and Umbria, showcasing medieval hill towns, stunning landscapes, local gastronomy, and rich history. This itinerary includes a dedicated stop for dining in Montepulciano and overnight stays in characterful accommodations.
Begin your scenic road trip from Florence, heading south into the beautiful Tuscan countryside.
Ensure you have your rental car picked up and ready for departure.
Discover the medieval charm of Siena, a UNESCO World Heritage site.
Visit the iconic Piazza del Campo, famous for the Palio horse race, and marvel at the stunning Siena Cathedral.
Parking available outside the city walls, followed by a short walk to the center.
Enjoy a delightful lunch in Montepulciano, a beautiful hilltop town renowned for its Vino Nobile wine and impressive Renaissance architecture.
Immerse yourselves in the local wine culture with a tasting session of Vino Nobile di Montepulciano, a prestigious red wine, and explore the town's historic cellars.
Consider a short, tailored experience with 'Just in Tuscany', a local tour operator specializing in wine and gourmet tours, to deepen your appreciation for the region's offerings.
Located nearby in Torrita di Siena.
Certified wine sommelier and tour leader. Great for a personalized experience.
Embark on a breathtaking drive through the Val d'Orcia, a UNESCO World Heritage site.
Stop at panoramic viewpoints to capture the iconic rolling hills, cypress trees, and picturesque farmhouses.
Many photo opportunities along the route. Consider visiting the 'Gladiator' viewpoint near Pienza.
Explore Pienza, a 'perfect Renaissance town' and another UNESCO site, famous for its pecorino cheese.
Enjoy a tasting at a local shop.
Drive to the stunning hilltop town of Cortona and enjoy a traditional Tuscan lunch with views over the Chiana Valley.
Engage with 'Do it in Tuscany - Tours & Services' for an exclusive, tailor-made experience in Cortona.
This could be a walking tour, a short cooking class, or a focused wine experience to truly immerse yourselves in the local culture.
Your local expert for exclusive, tailor-made experiences. Rated 5/5. Booking: https://www.tripadvisor.com/Attraction_Review-g187894-d7080914-Reviews-Do_it_in_Tuscany_Tours_Services-Cortona_Province_of_Arezzo_Tuscany.html?m=66827
Take some time to wander through Cortona's charming streets, browse local artisan shops, and enjoy the panoramic views.
Start your day with a scenic drive into Umbria, heading towards the beautifully preserved medieval town of Bevagna.
Wander through Bevagna's charming Centro Storico, visiting highlights like Piazza Filippo Silvestri, Vicolo Stretto, Porta Cannara, and the Colonna di San Rocco, experiencing its authentic medieval atmosphere.
Visit the Associazione Mercato delle Gaite, known for its medieval crafts festival, and the Cereria Medievale (medieval candle shop) to glimpse into the town's historical trades.
Drive to the dramatic clifftop town of Orvieto.
Enjoy lunch in one of its charming restaurants before exploring further.
Be awed by the magnificent Orvieto Cathedral, a masterpiece of Gothic architecture with its dazzling facade and stunning Signorelli frescoes.
Entry fee applies to the Cathedral and San Brizio Chapel.
Explore the fascinating subterranean city of Orvieto, uncovering ancient Etruscan caves, tunnels, and olive presses beneath the modern town.
Tours run at specific times and often require advance booking, especially in peak season.
Conclude your road trip with a final scenic drive to Orte, your ultimate destination.
This 3-day itinerary for Orte can be customized using our AI travel planner. Chat with our AI assistant to modify activities, adjust timings, add personal preferences, and get recommendations for restaurants, hotels, and transportation.