My Obsession with All Things Italian

By:  Jennifer Milano, written August 2015, udpated October 2016

Wherever I travel in the world, I routinely return to one place:  Italy.  Maybe my love of Italy originates from my ancestors, who emigrated from Amalfi about a hundred years ago.  Perhaps it is my passion for Italian food that makes me feel so at home when I'm in Italy.  Or it could be the years I spent studying the language, wishing to sound (and somehow look) like a beautiful, confident Italian woman speaking rapidly to her friends in a piazza, flowing words emphasized with an elegant flourish of hands. 

But really, my obsession with Italy is not so original.  Thousands of people around the world who have been fortunate enough to experience life in Italy share my enthusiasm for all things Italian.  But for me, when I am in Italy it means I have to shed my Type A persona.  If I expected my well-laid plans to go smoothly, for an orderly line to form in front of the train station ticket counter, or a repair person to show up at my apartment to fix a broken shower, I would only be setting myself up to go insane from frustration.  I am amazed by my ability to relax in Italy and adopt a "when in Rome" attitude.  Truly immersing yourself in the Mediterranean lifestyle goes hand in hand with feeling at ease and carefree.  And if I find myself beginning to feel perturbed by, for example, the gentleman in the camera store who managed to lose two months' worth of travel photos, I remind myself that such annoyances are largely outweighed by the beauty of a carefree life in Italy (although I am still pretty mad at that guy, who responded to our protests with the typical, exaggerated shrug of which Italians are fond).

I studied in Florence during college, lived in Rome while interning at the U.S. Embassy and traveled through many regions of Italy over the past thirty years.  I have a lot to say about Italy.  Below is an overview of each region or city for which I have travel tips.  For detailed information on transport, accommodations, restaurants and sites, just click the button for the region you are inspired to visit! 

General Advice for Traveling in Italy

Gelato: 

First things first.  Click here for my advice on finding authentic, delicious gelato throughout Italy.

Transport: 

Be aware that there are strikes in Italy, although usually they are announced a few days or more in advance.  Check online for announcements of strikes so you can adjust your plans accordingly (and if you are buying travel insurance, make sure it covers cancellations or delays due to strikes).  If you traveling between major cities or towns only, the train is convenient, and an affordable Italian rail pass is available.  If you want to explore the countryside, a car is essential (unless you are on a strict budget, in which case you should combine train & bus to get where you want to go, with maybe a day's motorbike rental for independent exploration). 

If you are traveling both city and countryside, I would probably get a car in the first city you visit, on the day you leave that city.  Navigating Italian cities is stressful, but dragging your luggage to train stations and renting cars in between when you are in the countryside is not that relaxing, either.  Be aware that Italian cities and major towns have "zona a traffico limitato", where you cannot drive your car absent permission that your hotel may obtain for you from the police.  Contact your hotel or apartment in advance to find out parking options if you are staying in the center of a city or town.  When making a decision on which airport to fly into, I consider what transport I am using.  If I am renting a car and the airfare is comparable to fly into a smaller airport like Pisa, I prefer that to landing in Rome and renting a car in Italy's busiest city.  If you travel on the motorways, choose a toll both that has a person in case you cannot figure out the automated machines.

After you park your car in an Italian town, take a photo of the closest street or cross-streets, so if you can't find your car later you can show the photo to a local, who will give you vague directions by hand gestures.  After several of these encounters along the way, you should find your car!  Also, my friend, Shannon, gives good advice for gated parking lots:  when leaving the lot, pay before you get in your car to get the gates will open.

You should definitely get a GPS unit for your rental car, and be aware that it won't always work.  Expect that you will get lost.  Embrace it, even.  Remember, it is hard to enjoy Italy if you expect everything to work as common sense indicates it should.  I also like to buy an old-fashioned paper map of the region, the most detailed of which you can find in Italy at a "tabacchi" shop.  Then, whichever person in your car is the navigator can begin the challenging task of reconciling the map, the GPS voice (which you will come to abhor no matter which accent you choose) and what Italy thinks passes for road signage.  In bocca al lupo!

Food: 

Naturally, food is one of your main motivations for planning a trip to Italy.  Just like anywhere else, avoid eating on the major piazzas or restaurants surrounding popular tourist sites.  If you want the atmosphere of sitting in one of the inviting cafes on a piazza, I suggest ordering a drink instead.  Save your meals for an out-of-the-way, authentic restaurant.  Read your guide books and online reviews, and try the restaurants recommended on this website.  Also, it may sound trivial, but try Lemon Soda (that is the brand name) sometime while you are in Italy.  It is made in Italy, and has real pieces of lemon in it - it is truly refreshing on a hot summer day!  For a cooking class, my friend, Shannon, highly recommends Il Castello di Gargonza in the Arezzo province of Tuscany.  The instructors were fantastic, the castle setting was beautiful, the price was right, and even her nine-year-old son loved it!  Click here for more information.

Festivals: 

One of our favorite travel memories is when the family who owned the farm where we were staying took us to a festival in a Tuscan village one evening.  A local festival is a great way to experience local culture.  In the summer months, look around the towns and villages you are in for posters advertising a "sagra" or "sagre", "festa or "feste".  Or, ask your hotel if there is one in your area.  Most villages in Tuscany and Umbria, as well as many other regions of Italy, host these festivals, and often have locals cooking up a specific food as the festival's theme.

For the kids: 

Italy is a fabulous country to explore with kids.  Italians generally love children, and derive great joy from indulging a child's every whim.  One guidebook geared to travel in Italy with younger children is called "Italy with Kids," which I've found to be useful.  We enjoyed the "agriturismo" life in Italy, which involves staying on farms.  I spent a lot of time emailing various farms, vineyards and olive orchards that offered rooms to travelers to find out if the owners had children, and if children are frequent guests.  I chose places where there were kids and swimming pools, and that had more than a few rooms so that the chances of there being more children staying there would be higher.  One vineyard in Tuscany secured our reservation because the owner replied to my email inquiry promptly, stating that his children would love to play hosts to my kids (they are all still friends today).  I also chose places that had amenities.  Many of the agriturismo choices are self-catering, which tend to be less expensive, and offer perks like kitchens and laundry facilities.  But when I am on vacation with my kids, I lean toward booking places that offer some meals, pool towels and staff to help organize activities and offer suggestions on outings.

I suggest researching child-centered tours and activities before leaving home, based on your and your children's interests.  In the region-specific pages on this site, I offer suggestions based on our experiences or reliable recommendations I have received.  If you are going to hire a tour guide, for example, find one who engages the children at their level.  They will be a lot happier, meaning you will be more relaxed, and all of you will learn from the experience (as opposed to a guide who talks over the children's heads, your kids start sighing and shifting their weight from foot to foot, you start whispering to them to listen and behave, they get annoyed and complain louder, and no one is having fun).  Older kids may enjoy a bike tour.  My friend, Shannon, recommends climbing towers, which are in virtually every Italian city, to entertain your kids and meet their energy-burning needs!

To both keep your children entertained and encourage interaction with Italian children, bring or buy a soccer ball.  I know it takes up space in your bag, but it is worth it.  Our kids made so many friends by just bringing the soccer ball to a piazza and starting to kick it around after dinner.  A ball is a kid-magnet anyway, but in Italy, a soccer game attracts local children like moths to a flame.

Accommodations:

I spend hours combing through TripAdvisor reviews, reading travel books and websites, and emailing villa and hotel owners to find the right places to stay with my family in Italy.  Here are a few of my tips:

• Check the "Specialty Lodging" tab on TripAdvisor for some vineyard and farm stay options
• Email hotel owners asking how many kids might be at the property during your stay
• Read, read, read those online reviews!
• Click here for an article by Wendy Perrin listing some villas to rent that are within walking distance of towns
• Consider hiring an expert to find your perfect villa or hotel, using Wendy Perrin's rolodex (click here)
• Check sites like vrbo and agriturismo.it for options
• Read my advice below for each region of Italy, where I recommend specific places to stay

Tuscany (including Florence!)

I begin with what is probably my favorite region of Italy, Tuscany.  One of my favorite memories is when my husband and I walked from our little room rental in Panzano in Chianti to the center of town, stopping along the way to remark on the endless views of the valley below.  We stopped at the local cheese shop and bought a piece of Taleggio, recommended by the vendor.  We bought fresh bread from the bakery.  At the village wine store, we picked up a bottle of - what else - Chianti.  We strolled back to our room, parked ourselves on our terrace, and savored our simple yet unbelievable Tuscan picnic. 

The views in Tuscany are so dramatic and peaceful, that even my four-year-old and seven-year-old were drawn to the (tastefully fenced) edge of our hilltop vineyard resort to just stand and look.  On this trip, we spent our two weeks in the Maremma part of Tuscany, which is now the most popular subject of my husband's and my retirement dream discussions.  La Maremma Toscana draws fewer tourists than the rest of Tuscany, but boasts both beautiful hilltop villages and seaside towns along sandy beaches.  In my opinion, it is the best of all worlds.

Tuscany's cities of Florence, Siena and Lucca are treasures filled with treasures.  Tuscany's small towns, countryside and villages provide endless hours of exploration and wonder. 

Puglia

Puglia is the heel of Italy's boot, and many travelers see only Puglia's unsightly ports of Bari or Brindisi on their way to or from Greece by ferry.  Recently, my family and I spent ten days exploring Puglia, and we loved it.  Puglia feels more rustic than Tuscany, and is not quite as alluring or magnificent as the Tuscan countryside, but is well worth a trip.  First, Puglia has some of the most beautiful beaches in Italy.  Picture the heel of Italy's boot - it is a peninsula, like Florida (sort of).  It is surrounded by water, with the Adriatic Sea to the east and the Ionian Sea to the west. Puglia has miles of sandy beaches and turquoise waters, and you can rent a pair of lounge chairs and umbrella on any of them for a fraction of the price you would pay in Tuscany. 

Puglia also has several delightful villages, each with its own character.  Puglia is less developed than the north of Italy, and Puglian towns do not have the glamour of Tuscan or Ligurian villages.  Some of the white-washed villages look more beige up close, as the houses haven't been cleaned or freshly painted in some time.  But these villages and towns are authentic, and lived-in.  Driving through Ostuni, we saw five elderly Italian gentlemen lined up on a bench in the center of town, talking animatedly and with a familiarity that suggested they had been meeting every morning on that bench for decades.  We loved the countryside of Puglia, too, staying at two different farms where our kids could swim and climb olive trees, while we were spoiled with freshly cooked food from the farm.  Puglia is famous for its conical-shaped buildings, called "trulli", which look like something out of a Disney fairy tale.  One of our farm stays included five nights in a trullo!

Rome

I love Rome.  Yes, it is a crazy, busy city filled with traffic and tourists.  Your patience will surely be tested more than once (a day).  But for me, the time spent wandering Rome's piazzas, exploring its ancient ruins and spectacular art, and experiencing the city's energy is well worth its hassles. 

The Amalfi Coast

Four of my great-grandparents left the Amalfi coast in the early 1900's, joining the millions of other southern Italians bound for America.  Now their great-granddaughter dreams of making the trip in the other direction.  Each of my visits to the Amalfi coast was only a few days long, just enough to make me wish for more time in Amalfi.  The coastline is unique and truly spectacular, the sea is clear and inviting, the food is incredible, and the summer evenings are festive, filled with laughter and gelato.  Just be aware that this is one of the more expensive parts of Italy.

The Italian Riviera & Cinque Terre

Rivaling the Amalfi Coast in beauty is its northern counterpart, the Italian Riviera and its famous five towns called the Cinque Terre.  Hiking the famous footpath that links the five villages, you are treated to fantastic views, leisurely lunches in seaside villages and spontaneous swims in the sea.  Just north of the Cinque Terre sit several more seaside towns where you can happily spend your summer beach vacation in true Mediterranean style.

Italy's Islands: Sardinia, Elba, Capri, Sicily & More

Planning an island vacation?  While Europeans routinely head for Spain, Greece or Italy to get on island time, Americans tend to visit the Caribbean, islands off the east coast of the U.S., and even Hawaii, which is further from the east coast than Italy's islands.  If you are looking for a different island escape, try one of Italy's beautiful islands.  You won't find a nonstop flight from the U.S. to any of Italy's islands, and hotels tend to be smaller and often lack the amenities of a typical "American" beach resort (i.e., water slides are contained in water parks, not attached to hotel pools).  However, you will still find gorgeous beaches, and have the added bonuses of being immersed in the Mediterranean culture and eating authentic Italian food for every meal (and gelato after (every?) meal)!  You will be on an island, but in Italy.  The best of both vacation worlds.

Italy's Lakes:  Garda & Como

Italy's lakes seem to take a second seat to the seaside, but they are beautiful, relaxing and worthy of a visit.  If you find yourself in the north of Italy, consider a visit to Lake Garda or Lake Como.  Lake Garda has gorgeous Alpine scenery, castle-topped towns and even an amusement park for the kids.  Lake Como features gorgeous lakeside towns and expansive villas, and its most beautiful town is only an hour and a half train ride from Milan!  (Tip:  airlines usually offer lower fares to Milan than to Rome.)

Venice

Also in the north of Italy is Venice, well-known for its myriad of canals and singing gondoliers.  Venice is a city built on 118 little islands, separated by canals and connected by enchanting pedestrian bridges.  Venice may be full of tourists (and therefore, expensive), but is so unique and lovely that it is worth at least a day or two of your vacation!