Spend a full day ‘Under the Tuscan Sun’ beginning with a visit to a local winery for a cellar tour, tasting of four wines, and a three-course lunch with dessert. After lunch, continue to Cortona, with its historic streets, lively piazzas, and beautiful views across the Valdichiana. Explore independently or add a private guided tour to discover more of this classic Tuscan hill town. The drive from Florence is about 1 hours and 30 minutes.

Insider Tip: Wear comfortable shoes, as you will be walking on the cobblestone streets of Cortona and possibly through vineyards.