A stone bridge studded with sculptures crosses the Tiber with a view of the dome of St. Peter's Basilica rising just beyond.

View of St. Peter’s Basilica in Rome. Photo © Valery Voennyy/123rf.

Unless you know Italy very well already, you’ll need to visit the areas where you might be interested in living. More than one trip will be necessary. The country is only the size of Arizona, but it’s as varied as the entire United States. There is an Italy that speaks German and eats speck and sauerkraut in the foothills of the Dolomites, and one that uses Arabic fishing methods in the southern Mediterranean. There are farming plains, vineyards, fishing communities on rocky coasts, villages clinging to volcanoes, and alpine fields and valleys. Italy even claims its own Wild West, with rodeos and lots of beef, in the Maremma area of Tuscany.

The differences between the North and South are profound, and you’ll only know which lifestyle suits you better after you’ve spent some time in each.Centuries of foreign occupation have left a mosaic of cultures with different values and priorities. You feel like you’ve just traveled to another country when you leave your office in Turin or Milan for a weekend in Bari or Palermo. The differences between the North and South are profound, and you’ll only know which lifestyle suits you better after you’ve spent some time in each.

Mostly, though, the decision on where to live in Italy will be narrowed down by what sort of work you do, if you work at all, and how much you can afford to spend. If you’re a career person, chances are you’ll need to make your home in or near one of the major cities. If you plan to open a bed-and-breakfast, you’ll likely look for more bucolic settings where tourism flourishes. Entrepreneurs often feel more comfortable with the North, where the work ethic is assumed to be higher. If you’re a student, you’ll be confined to cities with a university program—for foreigners, this often means Padua, Rome, Bologna, Arezzo, Siena, Perugia, and above all, Florence.

If you’re retired, well, you’ve earned the right to live just about anywhere you please, though it is a smart idea for homeowners of all walks of life to live somewhere near basic services, such as schools, hospitals, train stations, and airports. The dream of a country retreat can turn into a nightmare if the house is more than an hour from the nearest commercial center.

An initial fact-finding trip is a good time to check out the price of homes or apartments, meet professional contacts and potential employers (or examine the market for your business idea), and, hopefully, brush up on your language skills.

Reading English-language media about Italian current events and culture is one way to take the pulse of the country you’re about to call home. Before arriving, scour maps, cookbooks, and guidebooks and read as much as possible on the art and history of the place—you won’t know what you’re looking at in Italy unless you know the past.

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.

When to Go to Italy

Any experienced Italophile will tell you that late spring is the best time to visit. For Naples, Rome, Florence, Venice, and Milan, this is probably true. All of those places can be rainy in the fall, and summer, in my opinion, is out of the question.

But the harsh reality is that most people can only take time off in July and August, and if it’s their first time here, they want to see the major attractions. The trouble is that not only is every other North American, Japanese, Australian, and German tourist here in the summer, but many Italians are on vacation, too, and a lot of the shops and cafés are closed for a few weeks at a time. If you must come in the summer, it’s best to avoid the cities and head straight to the sea or the mountains. And book your hotels months in advance.

You will get much more out of your first stay in Italy if you come during the off-season. Every region has its own identity that expresses itself best in a particular time of year.

Early fall: Piedmont and Tuscany. These are the major winemaking regions, and if you want to taste Nobile di Montepulciano and Barolo, it’s always nice to visit the vineyards when the grapes are still on the vine.

Late fall: Emilia-Romagna. This is when the piadine (roll-up) sandwiches and salads yield to the hearty, trademark dishes of the Po River plain: prosciutto and culatello (a prosciutto delicacy), followed by tortellini and ravioli with red Lambrusco wine. Universities are in session, which means a lively atmosphere. Emilia, Bologna especially, is often said to have the highest standard of living in Italy, and also tops the charts for the percentage of people that leave in the summer, when it is a ghost town.

Most importantly, business is in full swing in the fall. To understand the glamorous reputation of Milan, you should see it when people return tanned and relaxed from summer vacation, the fashion models start to arrive, and the beautiful people put on parties. You might want to check out the calendar on the trade fair’s website, to see when the fashion and design shows are. (Usually, the Salone del Mobile design fair begins in April, while the women’s fashion shows are in late September and late February.) Conversely, you should stay away during those dates if you haven’t yet booked a hotel. The best restaurants also fill up quickly.

Winter: Turin, Veneto, and Alto Adige. The Dolomites need to be seen in the snow. If Easter should be done in Rome, Christmas should be done in Trento, in a frosty town with alpine scenery and heavy meals. Plus, the skiing at Madonna di Campiglio and Cortina d’Ampezzo is some of the best in Italy.

Spring: Everywhere else. Rome, Florence, and Naples are fine to visit in the fall but are at their peak in the spring. So are the Cinque Terre area of Liguria and the lakes region of Lombardy, both of which are in full bloom and enjoy perfect weather. The same is true for almost any pastoral area, especially Abruzzo and Umbria, which holds its cherry festival just after the winter.

Every region hosts hundreds of festivals and events throughout the year. (A nice database of them is at www.whatsonwhen.com.) Many are held in the summer—most notably, Spoleto’s music festival in June and the Umbria Jazz Festival and the Palio of Siena, which run in July and August—either for historical reasons or to dovetail with the tourist influx. Others, such as the Venice Film Festival in late August or early September, are timed to let the tourists get out first.

If, on your first trip, you’ve chosen a region and are reasonably sure this is where you’d like to live, it’s always best to come a second time in a different season. You may have fallen in love with Puglia or the Italian Riviera during your stay in July, but do you realize how lonely it can get there in the winter? Like all resorts, the Italian lakes and coastlines are buzzing with festivals and activities in the summer, but it’s all downhill from there.

Northern cities like Milan may seem an ideal choice for urbanites, with their swank shops, cafés, and cosmopolitan population, but most of these disappear in July and August, when the humidity and mosquitoes descend. Similarly, Venice—aka “la Serenissima”—is indeed the most serene and romantic city in the world in the offseason, but feels more like Disneyland when the tourists start arriving in May.

A city or region that was off-putting on your first trip might take on redeeming qualities if you come back in a different season. You should try short-term rentals in a few places in various months before starting an earnest search for a house.

Again, keep in mind that you won’t be able to get much real estate business done in the summer. In other seasons, a three-day weekend in Italy can magically turn into a week, so don’t plan to reach agents or even homeowners in the periods around Christmas, New Year’s Day, and Easter.

What to Pack for Italy

You will need plug adapters for all of your U.S. electronics. For any large appliance, such as a printer or a blender, you should have a 110- to 240-volt transformer. Your laptop and other commonly portable devices should already come with one.

Remember that videocassettes and DVDs are on different systems in Europe. VCRs in Europe run on PAL, or Phase Alternating Line, not the U.S.-style NTSC, or National Television System Committee. (Italian camera operators, who swear that PAL offers more consistent quality, joke that NTSC should stand for Never Twice the Same Color.) Media companies have also set up separate DVD codes in Europe to prevent sneak previews of movies not yet released overseas. If your computer has a DVD player, be warned that you will be able to switch back and forth between European and U.S. systems only a few times, and then the computer will experience problems.

By all means, buy any accessories for your computer or digital camera before you leave; not only are they more expensive in Italy, but many brands are not as common here, and stores may not have what you’re looking for. Also, pick up any software before you leave, unless you want the Italian-language version.

Other items that you should bring along for any extended stay include: tax documents, if you’re traveling in the filing season (though the U.S. Embassy and Consulates have all the necessary forms); a résumé and any letters of recommendation; a photocopy of your passport (tucked in a separate suitcase) in case the original is lost or stolen. It’s hard to get a replacement without the copy.

Packing a load of aspirin is a good idea, since it can only be bought at pharmacies, as well as any prescription medication you may need. Also, if you are particularly prone to colds, pack a good supply of decongestants. I still cannot explain why pseudoephedrine tablets (unless mixed in minuscule doses with unnecessary agents for fighting the flu) are so difficult to acquire in the average pharmacy. Other than that, the toiletry aisle of an Italian supermarket looks almost identical to one in the United States.

Dressing for the Weather

Depending on the time of year, packing clothes for Italy can be simple or very tricky. The dozens of different climates have their own weather patterns in different seasons. The only constants are that the Alps are very cold in the winter, and everywhere else is torrid in the summer. Especially in the North, the humidity can be suffocating. Rains there come like clockwork in early September and mid-November, and you can count on a snowstorm or two just after Christmas. In the central regions and the South, you can usually get away with just a jacket in the spring and fall, and make sure to bring very light clothes for the summer. Except maybe during the week in early August, when the heat is absolutely dizzying, Italian men never wear shorts in the city. If you think it’s important to fit in, bring along some light linen pants and a few dress shirts that breathe.

Excerpted from the Third Edition of Moon Living Abroad in Italy.