Book a direct flight into Rome, the capital of Italy. Use Rome as your base for travel to other areas such as Tuscany to the north and Sicily to the south.
Book domestic Italian travel. First travel to Sicily for a stay in the beachside village of Taormina. Then visit Venice. Use a low-cost European carrier such as Ryanair, Blu-express and Wind Jet. Fares can be as low as 5 euros.
Pack clothing for a range of climates. September can be warm or rainy. Sicily requires shorts and a swimsuit. Expect cool nights in Tuscany.
Use the transatlantic flight as a time to rest and learn. Try sleeping to make time-zone adjustment easier. Brush up on the Italian language during the awake hours, mastering "ciao" and "buonna notte," the words for "hello" and "good night."
Use cheap and efficient public transportation to get to your hotel and around the city.
Examine maps and get recommendations from the concierge about local restaurants, religious festivals and sites. For example, the Roma Europa Festival features artists from across Europe in theater, music and dance performances from September to October.
Travel by train to Florence for an overnight trip. Visit the medieval town of Certaldo Alto, in Siena's wine region, for the fall culinary festival. Although Certaldo Alto is accessible by trains that depart hourly on the Florence to Siena line, consult Borghiditoscan.net for other methods of transportation.
Sit in a local cafe, sip cappuccino and eat gelato. Reflect on the tastes, sights and culture of your surroundings before returning stateside.