Start your journey in Siena at 9:30 AM and head to the enchanting medieval hamlet of Lucignano in the province of Arezzo. Stroll through its charming concentric streets, a unique design that has earned it the nickname "the town of the golden tree," and soak in its romantic atmosphere and historic allure. Next, continue to the vibrant city of Arezzo, a treasure trove of art, history, and architecture. Explore its stunning Piazza Grande, framed by medieval towers and Renaissance elegance. Marvel at Piero della Francesca's fresco cycle in the Basilica of San Francesco, and admire the intricate craftsmanship of Giorgio Vasari’s House. Arezzo’s rich history and artistic heritage will captivate you at every turn. After sightseeing, retreat to the tranquility of a countryside farm for a wholesome Tuscan lunch featuring fresh, local ingredients and paired with delightful wines. Here, you’ll savor the flavors of the region in a warm and welcoming setting. In the afternoon, visit the hilltop town of Cortona, famously depicted in Under the Tuscan Sun. Meander through its steep, picturesque streets, discover ancient Etruscan roots, and enjoy breathtaking views over the Valdichiana and Lake Trasimeno. Return to Siena after approximately 8 hours, enriched by the insights of your knowledgeable guide. With a small group of no more than 8 participants, this intimate tour offers a perfect blend of history, culture, and culinary delights.