Purchase a pre-planned, guided vacation package. A number of tour groups such as Delicious Italy, Tuscan Way and Italian Horizons offer getaways that teach you about the food and wine of Italy, one of the country's biggest attractions. On these tours you can learn how to cook and make wine as well taste a number of authentic dishes. Many tours are inclusive, with the price covering meals, travel and accommodations.
Educate yourself about the large cities and countryside villages if you prefer not to purchase a guided tour. Cities such as Milan and Venice are geared toward tourists who want to visit popular attractions. But be sure to veer off the beaten path into the smaller villages to see what Italian life is really like. Book a room at a bed and breakfast, mingle with locals at a cafe and eat at restaurants only locals know of.
Take a guided bus tour. This is a way to make use of travel expertise even if you still do most of the planning yourself. A professional knows all the popular cultural spots in Italy. Within large cities such as Milan, Rome and Venice you can take hop-off/hop-on loop tours. Companies that offer these tours include Guest in Italy and Road to Italy.