Italy Itinerary #1: Taking the Road Less Traveled

Here are the first of what will be many personal recommendations for exploring Italy.


It never ceases to surprise me how many Americans come to Italy for a week to ten days during the three hottest months of the year and then end up visiting the same four cities (Rome/Florence/Pisa/Venice), with most of that time spent traveling on a tour bus. They complain about the heat. They complain about the lack of air conditioning. They complain about the crowds. But I am usually met with blank stares whenever I try explaining to these disgruntled travelers that Italy, real Italy, is only imperfectly discovered in her major cities. It is on the roads less traveled that a visitor will find her.


The problem is, so few are willing to risk it—or risk anything. They want the comfort and convenience of familiarity. It’s why they go to Starbucks in Rome instead of the thousand bars that serve better coffee for less. It’s why they go to McDonald’s instead of any number of trattorias offering authentic Italian fare. It’s why they go where they’re told to go. And that, to me, is the most tragic thing of all.


I’m going to suggest an itinerary that will provide far greater satisfaction than the same old tired tourist traps, but I don’t want you to blindly follow my suggestions either. You need to research the places I’m talking about, and see if they’re fit for purpose. Your purpose. Only then will you be able to discover the real Italy, the one that isn’t featured in heavily filtered photos on some tour operator’s spammy Instagram feed. I am, in fact, offering you for free an eight-day independent travel itinerary that makes an efficient use of time and distance so you don’t waste your precious vacation hours gridlocked on the A-1 with a whole bunch of tailgating, fist-shaking, hyper-caffeinated Italian motorists.


No one deserves that.


All of the following advice is coming from someone who has lived in Italy for almost a decade. I am not being compensated in any way for these endorsements. If I were, I would be the first to tell you. Funny, isn’t it, how poor creative class people like myself are about ten thousand times more trustworthy than wealthy celebrities like Kim Kardashian, who just today was ordered to pay 1.3 million dollars in fines for promoting crypto tokens without disclosing that she’d been paid to do so. I’m not saying that poor people are more altruistic, more likely to give what little they have to others, and are just generally better human beings … except, oh wait, I’m totally saying that.

So, three things before we get started.

  1. Italy needs to be explored regionally. By that I mean you can’t do a pastiche tour of Italy (Rome/Florence/Pisa/Venice) and expect to get anything out of it. You won’t. Italy is a country you must—and will want to—visit again and again. Are you primarily interested in museums? Then build an independent travel tour around museums. Do you like beaches? Then stick to the coastline and avoid traveling into the center. We err in trying to do too much, especially in a country that by its very nature offers a stern rebuke to the ambitious. Italy doesn’t want you darting everywhere at once like a hornet in a jar. She wants you to slow down and savor. It’s practically the whole point of being here. There are twenty separate regions in the Republic of Italy. Time and money allowing, I might pick five and visit each as a separate vacation. That might look like Puglia one year (hands down, the best food in Italy is to be found in Puglia), Trentino Alte Adige (think: glorious alps), Tuscany or Umbria (Umbria is the less touristy but equally beautifully “green heart” of Italy, around which I am designing my first itinerary for you), Liguria (also known as the Italian Riviera for its ravishing coastlines) and then Campania (coastline and food, food, food). You could also do Sardegna as a region (Sardegna is an island that the writer D.H. Lawrence once described as “lost somewhere between Europe and Africa and belonging to nowhere”) or Sicily. The farther south you go, I find, the stronger the flavor of Italy.

  2. Exploring Italy one region at a time means less scuttling from one hotel to the next, less packing and unpacking, and less time wasted on the road. Instead of four hotels, you pick two B&Bs and range out from there. You will be happier, less rushed, and better able to take in the beauty right in front of you instead of worrying about making it to the next stop. Additionally, I am steering you away from touristy places, so if you like crowds, lines, and tourist menus, this Cappuccino probably isn’t for you. Also: avoid traveling here during the summer. September is arguably the best month to visit, followed by October, April, and November. Independent travel means you will need a SIM card for your phone so you can make full use of features like Google Maps. My understanding is that some providers (AT&T, for instance) has a ten-dollar-a-day international plan. Barring that, if you have a U.S. phone, especially one that you’re paying for on an installment plan, it is most likely “locked.” U.S. telecommunication companies like to lock phones so you can only use them on their carriers’ networks. Not so in Europe. If you buy a SIM card in Italy, say, it’s good for the entire European Union—no roaming fees. That’s because Europe actually has (and enforces) consumer protection laws. Imagine! Be sure to call your provider before you come to Italy and make sure they unlock your phone so it can receive a third-party SIM card. For more information, click here.

  3. To explore Italy regionally requires a car. Because of supply chain issues, the war in Ukraine, a shortage of computer chips, gas prices, unbridled greed and other variables, the cost of renting a car in Italy—even off-season—is shocking. As of this writing, a two-week rental at the most affordable agency I know, which is Centauro, is over 400 euros. Thankfully, the U.S. dollar is near or at parity with the euro right now, so that’s roughly 400 dollars. For two weeks. A few years ago, I could rent a Fiat 500 (I love Fiats!) for 250 euros for the whole month. But those days are gone, I’m afraid. This is what we’re now stuck with. I have also rented cars through Qeeq, which is a price consolidator that may have been recently acquired by LinkedIn. Their interface is certainly smoother than it was previously. And if you can get a better price on a car rental there, more power to you, but I like and trust Centauro, even though they claimed I melted a hubcap once and made me pay for it. Still cheaper and more trustworthy than Sicily by Car or some others. Sixt is good, but they’re expensive. Many of these agencies, such as Goldcar, rack up so many bad consumer reviews, they are forced to change their corporate skins and trot themselves out under a different name. Best to avoid any suspiciously new car rental companies.

Here then is one of a series of proposed itineraries I will share with you on the proviso that you feel free to improvise, do your own research (what I like may leave you feeling flat) and realize that my opinion is not the definitive opinion. These are not the usual places by any stretch, so expect to have a truly unique experience. At least that much I can promise you. But to tell you the truth, no matter where you find yourself in Italy, you’re going to see magnificent things. That’s just the way it is here. You can’t go wrong. Itinerary #1: Umbria (the less touristy Tuscany) Amelia-San Gemini-Deruta-Perugia-Todi-Gubbio-Spoleto.


Why I recommend Umbria: if you like undulating hills, wine tastings, trellises covered in grape vines, breathtaking medieval borghi perched atop cliffs, hand-painted ceramics, bustling Italian villages, and views for days, Umbria’s got your back. It’s a mystery to me why Tuscany absorbs most of the tourism, especially when Umbria is here, largely untouristed, drowsing in the Italian sunshine.


Fiumicino in Rome is the closest airport to Umbria (Rome you can do another time), which will take you about 90 minutes to get to. Your first stop is Amelia, a village that’s seven hundred years older than Rome, possibly the oldest village in Italy. At the top sits the Duomo, which is actually worth the hike, and if you’d rather not hoof it, small electric buses are available to take you at least most of the way up. The 360-degree views of the countryside are incomparable, as are the many Renaissance palazzi, the museum, the Roman cisterns, and a jewel box of an 18th century theater, Teatro Sociale. If you’d care for a bite, there’s Russo, which is one of the best bakeries in town. More substantial fare can be had at La Locanda (five stars, truly) and Dentr’Amelia, which sits across from a fun, funky bar called No Way. For terrific pizza, burgers, fries, and Italian food, I recommend Porcelli Tavern, which is run by a local legend named Valda.


Amelia at sunset

Remember: there’s very little tourism on this itinerary. Don’t be surprised if you have some of these villages mostly to yourself. That’s one of the reasons I’m recommending them.

After a busy day, you might want to actually sleep in Amelia (I strongly recommend La Gabelleta, which is far and away the most beautiful area hotel), and then after a leisurely breakfast, start making your way north to San Gemini.


Characteristic view of San Gemini

San Gemini is one of those sleepy Italian villages that beguile you with sweeping views, the Marmore falls (less than two miles away) and a delightful “surprise for the eyes” around every corner. Feel free to have lunch there, and then make your way toward Deruta.


The charms of Deruta

Deruta is a charming village known for its Italian maiolica, tin-glazed pottery decorated in patterns and colors and set against a white background. You can spend a little money there or a lot of money there, depending on your budget, and most vendors are happy to ship your treasures back home. From Deruta, I would head back to La Gabeletta for dinner and bed.

Next morning: Perugia, the capital of the Umbria region, which usually bustles with activity. You will hear English spoken here because of the Università per Stranieri, University of Foreigners, where Italian culture is taught to students from around the world. Having said that, there’s very little of the kind of parrot shirt, camera-on-a-neck-strap, white-socks-and-sandals tourism you might be looking to avoid. Enjoy the Basilica of San Pietro with its medieval crypt, the Galleria Nazionale dell'Umbria, which houses some wonderful collections, or feel free to walk around. I often prefer to do just that, wandering aimlessly down deserted alleyways that invariably lead to belvederes (overlooks) that make me feel as though I’m the only one who knows they’re there.


One of Perugia's lush piazzas

I might think about finding a nice B&B in Perugia (there are plenty) and using it as your next launching pad for all parts north. If so, the next morning you will head out to Todi.


The hilltops of Todi

Todi is a hilltop town that offers you panoramic views of the Tevere Valley. In addition to the 14th-century Priori Palace and St. Fortunato Church, you can visit the 16th-century Consolazione Temple or stop to sample local delicacies like pan caciato, a small loaf made with walnuts, cheese and raisins. Expect a hike. Italy’s hilltop towns make demands on the knees and cardiovascular system. And they are 100% worth it.


Personal photo of lovely Todi

The next day, set aside the whole day for Gubbio. There’s a reason this village finds its way not only into the Zagat’s guide, but the hearts of all who behold her. Nestled into the foothills of the Apennines, Gubbio will dazzle you with her hidden piazzas and forbidding-looking castles. There are more palazzi, theaters, mausoleums, aqueducts, duomos and basilicas than you will have time to visit—and yes, there will be some tourism there, although not nearly as much as Italy’s major cities. If you are a fan of truffles or truffle oil, Gubbio is where you will find them.


I would hit Spoleto on the way from Perugia (assuming you are staying there) to Rome, with the idea that you will sleep one night in Rome before heading back home. Spoleto beggars the imagination for any words that do service to its remarkable beauty. Turning a corner and seeing the massive Rocca Albornoziana fortress is not an experience you are likely to forget, but then neither of the Duomo of S. Maria Assunta, which this picture does no justice to. Truly, you will glut your senses on all the lovely things to see here. The San Pietro church, which you will spot from the highway and yearn to visit, is actually prettier on the outside than the inside. I’d save myself for the centro storico (historic center) of Spoleto itself.


Duomo of S. Maria Assunta in Spoleto

From Spoleto, you will travel to Rome, maybe do a tiny amount of sightseeing, have dinner, and then catch your plane home. What I have described is, in my estimation, the best way to experience the beauties of Umbria. There have been some purposeful omissions, not because I have anything against places like Orvieto (which is well worth visiting) but because there is simply too much tourism there. So don’t anybody @ me.


In the coming weeks, I will cobble together more fun itineraries for you, and I certainly welcome any suggestions. Until then, enjoy your dreams of Italy.


Copyright © 2022 Stacey Eskelin