Whether you are a returning visitor to Tuscany or this is your first time in Italy, Cortona is the ideal base for exploring both central regions of Tuscany and Umbria. Located in the heart of the Tuscan wine country, just over 2 hours north of Rome airport and a bit over a 2 hour drive from either the Tyrrhenian or Adriatic coasts, the town of Cortona is well situated. Positioned at the top of a 600-meter (2000 ft.) mountain, in typical walled, Italian hill town fashion, Cortona was a thriving Etruscan community by the 8th century BC, making it truly ancient by any standard. It is considered by pundits to be the among the most picturesque towns in Tuscany today.
Although the year-round population inside the walls of this walking town is only an intimate 1,500, it swells to many times that during the peak season from May to October, as Americans flood in to experience the legend of Frances Mayes’, “Under The Tuscan Sun” for themselves. At first blush, this may sound unattractive but the benefits to this seasonal influx are many, including over 30 excellent restaurants to choose from, as well as a steady stream of exciting and interesting festivals and other sponsored events and all manner of desirable goods and services. 

Cortona is also on the regional rail line running north, direct to Florence and south direct to Perugia and beyond. The local train station in the adjacent town of Camucia (pop. 5,800), is 5 minutes from Villa Bacchino.
If you enjoy exploring Tuscan cultural centers, take the 1 hour drive for a day trip to the city of Siena (pop. 54,000) with its central piazza, Il Campo, the Palazzo Pubblico and impressive marble Duomo. Arezzo, (pop. 100,000) within 40 minutes of Cortona by train or car, is home to countless antique shops, museums, Etruscan walls and a Medici fortress. The city of Florence (pop. 380,000), arguably the center of northern Italian culture, is only 1hr. 20 minutes from Cortona by car or train.
Cortona is in the heart of Chianti, so if whiling away the afternoon tasting wine in a bucolic Tuscan vineyard is your thing, there is a plethora of wineries to visit within a short, 30-minute drive of Cortona. The tiny, picturesque hill town of Montepulciano (pop. 14,000) and its famous Vino Nobile wines is a 40-minute drive and equally cozy, Montalcino, (pop. 5,100) in the center of the Brunello wine region, can be reached by car in about an hour.

Cross the nearby border into Umbria and you will find two of the larger medieval towns of Perugia (pop. 166,000) and Città di Castello (pop. 382,000) with their grand Palazzi, cobbled streets and views over the mountainous landscape.
Tuscany and Umbria are two of the best regions for hiking and cycling, making it a great destination for outdoor lovers. Lago Trasimeno is the fourth largest lake in Italy and is within 13km of Cortona — a great day out for relaxing on a sandy beach or enjoying lunch overlooking the lake at Castiglione del Lago (pop. 15,000). 

Spring temperatures are pleasant throughout Tuscany and Umbria, including Cortona. An average daytime high temperature of 21℃ (70℉) in May makes it an ideal time for walking, biking or just about any outdoor activity.
Summer is high season across Italy and daytime temperatures around Cortona rise to an average high of 30℃ (86℉), with lows of 14℃ (57℉) overnight. Generally low humidity tends to moderate the heat on all but the hottest days and make sleeping comfortable even without air conditioning most evenings. This is the season for sunbathing by your own private pool or on a sandy beach on the shores of Lake Trasimeno. Venture into Cortona’s historic center by evening and you can enjoy the buzzing atmosphere of the town's main piazzas.
Cooler Fall temperatures, in September and October, thin the crowds and are great times to visit Cortona and the surrounding hill towns at your own pace.
There are plenty of food festivals and events happening year-round, in and around Cortona. Cortonaweb.net is an excellent website to get more details