Preparing to Leave Traveling to Italy in this day and age couldn’t be much easier. There are several direct flights per week from the United States to Rome and Milan, even Pisa, and lots of connecting services to other cities. Plus, there is a field of low-fare airlines that fly from European cities to smaller Italian airports. For European Union countries that adhere to the Schengen agreement, such as Italy, there are essentially no visa requirements for Americans staying fewer than 90 days. The only health issue is making sure your insurance covers you overseas”Medicare will not. Customs regulations are no stricter than they are in the United States”in fact, they are more lenient in many respects. After about a dozen flights to Italy, I’ve never actually had my suitcase checked by customs. One might assume that this has changed in a post September 11 world, but for better or worse, it hasn’t changed much in Italy. Just remember not to bring in perishable food items or huge stacks of currency.