The best times to visit Tuscany and Umbria are in the spring and fall. Umbria's countryside is at its best in May, garlanded with flowers and spring green, and blessed with weather that is already pleasant. July and August are the most crowded months and watch out for festivals and holy days, especially in Assisi (Easter is particularly busy). September and October are good months in town or country, and are often drier than the spring months, though summer sun will have left Umbria's green heart looking brown and parched.

Starting in late May, the summer tourist rush really picks up, and from July to mid-September the country is teeming with visitors. August is the worst month to visit. Not only does it get uncomfortably hot, muggy, and crowded, but the entire country goes on vacation at least from August 15 until the end of the month, and many Italians (especially in the cities) take off the entire month. Pisa is virtually deserted in August. Many hotels, restaurants, and shops are closed - except at the spas, beaches, and islands, which are where 70% of the Italians are headed.

January and February are cold, but often dry, and with so many indoor cultural attractions (galleries, churches, museums) and only locals in the restaurants, the region can be a joy to explore at this time of year. In winter (late Oct to Easter), most sights go to shorter winter hours or are closed for restoration and rearrangement, many hotels and restaurants take a month or two off between November and February, spa and beach destinations become padlocked ghost towns, and it can get much colder than most people expect - it may even snow on occasion.