This Former Travel Agent Has Advice on How to Vacation in Italy

Do you cruise, tour, or wing it? Here are some things to think about.


Italy cities to visit according to Stacey Eskelin at Cappuccino
Amelia, in the region of Umbria, the oldest village in Italy

In one of my previous iterations as a single mom running madly on the capitalist hamster wheel, I sold resort packages and vacation tours. I was good at it, mostly because I yearned to travel the world myself, but also because I listened to what a client told me—and didn’t mean to tell me—regarding his comfort-level with being uncomfortable.

That’s the key to travel that most people don’t realize: being able to brook massive inconveniences, personal discomfort, communication snafus, dealing with humanity at its best, dealing with humanity at its worst, and negotiating possibly violent gastrointestinal showdowns at inconvenient moments in cities with no public restrooms when your innards have mutinied against the introduction of new microbial flora and fauna.

If you’re not comfortable being uncomfortable, seriously, don’t travel.

Not everyone is cut out for it. Some folks are happier staying home—and frankly, I don’t blame them. Comfort is wonderfully addictive. You’re in a climate-controlled environment with all your stuff. Food-wise, there are no exotic surprises (unless you’ve neglected to empty the refrigerator). You can usually speak the language.

Meanwhile, nomadic jackasses like me are standing shoeless on a filthy floor at the airport wondering if this is really what our lives have come to, waiting to get barbecued by the backscatter X-ray or groped by a TSA agent because fifty years ago some dillweed got caught toting an underwear bomb. Who knew that going from Point A to Point B would become a raw Darwinian struggle pitting travelers against a system so controlling, oppressive, unfeeling and cruel, you start dreading it from the minute you book your flight.

So, yeah. Don’t travel unless you’ve got a serious itch that can’t be scratched.


That said, there are ways to do it—insider ways—if you’d like to make Italy your next destination. And I can help you there, both as a former travel agent and as a long-time resident of the country. Should you take a tour or travel solo? Go by train or rent a car? What are the advantages to doing what I call a “pastiche” tour, covering lots of cities in a short amount of time, versus an intensive “staycation” where you rent one, maybe two, B&Bs and embark on day trips from there?

Like I mentioned at the top of this article, the first rule is to “Know thyself.” Are you an ambi- or extro- vert? Would you prefer not to handle hotel accommodations and transportation arrangements? Does the idea of standing around in an easily identifiable clump with others of your kind (Look! Americans!) not fill you with a feeling akin to horror? Then you might just be what I call “Tour Material.”

Upsides: Your transportation to and from the airport is usually provided. You won’t have to worry about missing a train, falling victim to a wild goose chase, getting lost, starving to death because you’re stuck out in the middle of nowhere and all the restaurants are closed by 9:00pm, contacting your Airbnb host at two in the morning because you finally arrived only you can’t get inside, forgetting that in most Italian villages, stores are closed between 1-4pm, or overcoming a considerable language barrier. Within the EU, Italy and Spain were the only two countries where English-language skills are classed as “moderate” rather than “high” or “very high”. Don’t expect everyone to speak English. You’re in a foreign country. It’s not their job to speak our language; it’s our job to speak theirs.

All this to say that the upsides to taking a tour are myriad.

So what are the downsides?

I don’t like many people (that feeling is most assuredly mutual) and the idea of making idle chit-chat with strangers is anathema to me, so perhaps I’m overemphasizing this aspect of taking a tour, but please remember that you’re married to your tour mates for the next week to ten days. You’re going to have breakfast with them. You’re going to talk to them on the bus. Most nights, you’ll have dinner sitting shoulder-to-shoulder at a tourist-menu restaurant. So if the idea of being trapped for eternity with Al and Enid Wilson from Weedhole, Oklahoma (she’s a retired second-grade teacher; he used to sell insurance) makes you want to jump to your painful death, a tour is probably not for you.

To be fair, people who are a lot more extroverted and people-y than I am have formed solid, lifelong friendships on their tours. The same can be said for cruises. It all depends on who you are.

But there is no room for spontaneous detours (notice that word there—”DE”-tours) when someone else is setting the agenda. You’re going to go to their destinations within major cities, usually the ones they have an “arrangement” with. That cute trattoria you saw earlier? Make sure you know before you book the tour how many free nights you are allowed to do your own thing. Some people want at least a little freedom, but most won’t set foot outside their hotel.

There are a million tours, and I invite you to do your own research to see which ones survived the economic plague that is Covid, but Gate1 has upped their game quite a bit in recent years, having gone from a bargain basement provider of mediocre tours to the same, only now with a painful new knowledge that too many bad ratings will sink you. Upside: you can, within reason, customize your own tour. They call it “independent travel,” but to be frank, these are all things you can do for yourself at half the expense, which is why I suggest doing a tour or traveling independently. Don’t mix.

Tauck Tours are expensive, but you get your money’s worth. They also do small ship cruises and river cruises. Your tour guides are usually courteous, professional, and knowledgeable about the area. But you’re still doing six cities in eight days. That’s a lot of moving and packing, moving and packing. The nice thing about a cruise is having to do that only once before you head home.

Globus Tours offers many of the same tours for less, but expect to spend a lot of time on a bus. I get sick on buses. They are not for me. Doing what everybody else is doing is also not for me. I’m restless, curious, and defiant. It’s not in my nature to follow rules. I am the exact opposite of Tour Material.

Which is why I’d like to talk to you about traveling independently, and I’ll start with the major caveat that it’s not for everybody.

  1. You will get lost. Signs in Italy are notoriously vague and even nonexistent. If you don’t have an Italian SIM card in your phone, you won’t be able to use GPS. Your rental car may or may not have GPS, but even with GPS, you might not know where to go. There are a million dead zones here, particularly at higher elevations, so keep a sense of humor and know that Italy brings a whole new understanding of “It’s the journey, not the destination.” Don’t panic. Nobody’s going to cannibalize you on some back road.

  2. Driving in Italy is not for the faint of heart. Italy is a country full of hyper-caffeinated lead foots who consider aggressive tailgating to be a “gentle reminder to drive faster.” Some of the roads are barely paved and rutted with potholes. Others aren’t paved at all. We have these diabolical things called Autovelox, which are roadside speed detectors. They wouldn’t be a problem if the authorities could be bothered to post a speed limit, but a lot of the time, they don’t, so, steady goes.

  3. Parking doesn’t actually exist in the way you understand it. Italy is a medieval country. No one saw the modern-day SUV coming. When you’re at the car rental agency and they try to upgrade you to an SUV, you’d be wise to say no. I prefer a nice Panda or a Cinquecento. Not only are you going to be squeezing that beast through narrow, cobblestoned streets, you are going to have to parallel park it, too, sometimes on an incline. Out of necessity, Italians park on sidewalks, in bushes, next to 1,000-year-old walls. All of these inconveniences need to be taken into consideration when deciding whether to go on a tour or go solo, and especially whether to accept an upgrade.

  4. Trains are an option, but … Italian trains run on Italian time, which is it say they show up when they want to. I, personally, find the Italian train system to be maddening and unfathomable. You have your regional trains, which make frequent stops and are agonizingly slow—slow as in snails mating. Then there’s Trenitalia, Italy's state-run rail network, which operates most of Italy's high-speed Frecce trains. They’re fast, but they’re not cheap, and they mostly serve the major cities. This then leaves you at the mercy of Italy’s bus system, and that stuff is not for amateurs. If you think catching a train is a fun challenge, try getting a bus. True story: my boyfriend, John, got a flat tire driving to work one day and was forced to take a bus to Rome. He tried buying a bus ticket (they must be purchased from a bar or a tabacchi—unless you want to pay a lot more on the bus) but it was already between the hours of 1-4, which is when everything’s closed. With no choice but to take his chances, he got on the bus, and at the very next stop, three controllers came onboard to check everyone’s ticket. Failure to provide one results in a hefty $100 fine. Between the tire and the ticket, John ended up deep in the hole that day, even after he went to work.

  5. With no one to help you overcome the language barrier, you will become the world’s most awkward mime. Unless, of course, you wisely spring for an Italian SIM card, which I was too poor to do on several occasions. Having a SIM card makes all the difference, whether you’re trying to decipher a menu, figure out directions, pull up a train schedule, or use the handy-dandy speak-to-text translator on your phone. The SIM card pays for itself in a thousand ways. Make it the first thing you do after you disembark your plane. Your two telecommunications options in Italy are likely going to be TIM or WIND. Pro tip: always, always, always bring a smartphone battery charger with an adaptor. Italy is many wonderful things, but well-provisioned in wall sockets is not one of them, and at the least convenient moment, you will run out of juice. Also, in a possible precursor of things to come, Italy has not one, not two, not three, but FOUR different electrical wall outlet plug types. Behold the most common ones:


With so much to be wary of, what’s the upside to traveling on your own?

Is there an upside?

  1. To me, the “real” flavor of Italy can’t always be found in major cities like Rome, Florence, and Milan. You are required to take the road less traveled, get lost, end up somewhere fantastic that no one’s ever heard of. If you hate touristy places as much as I do, you mustn’t restrict yourself to the six-cities-in-eight-days deal, because all you’re going to get is touristy places. Random beauty you see when taking the road less traveled. Photo by Stacey Eskelin. Italy is discovered in its sleepy medieval villages. It’s what you find after you’ve been looking for some place else. It’s having to stop on the road for twenty minutes while a herd of sheep crosses in front of you. It’s taking coffee in a drowsing piazza and then wandering through the most breathtaking church you’ve ever seen, which is sitting right there with its doors ajar and no one inside but you. Italy is about pulling off the main highway when you see something irresistible. It’s about 6:00AM church bells and the scritch scritch of Italian nonnas sweeping their front stoops. It’s about the old men with their bald heads playing cards at a social club. It’s about knowing that things endure, but people do not. We’re born, we live, we die, but Italy is forever.

  2. Travel isn’t about checking all the boxes. It’s about the adventure. Anyone can say they’ve been to Florence. But how many people can say they’ve stayed in Calcata or had cappuccino and a cornetto in the fortress overlooking Spoleto? Will there be surprises along the way? I hope so. Isn’t that the entire point of going to a foreign country? To let go of the vacation we’ve planned and embrace the one that’s waiting for us? To hear the chime of a church bell shimmering through warm, honeysuckle-scented air? Life isn’t meant to be experienced through a computer screen or a bus window. We’ve grown far too accustomed to having our travel experiences packaged and delivered to us so that we remain observers, not participants; consumers, not actors. Don’t keep coloring inside the lines. In fact, throw away the coloring books altogether. Pick a region (e.g., Liguria, Umbria, Tuscany, Lazio, Veneto, Valle d’Aosta, etc.), book a B&B, and let yourself range out from there. If time and money allow, do the same thing in a second region or a third. But trying to see and experience all of Italy in one trip is like trying to eat a massive hot fudge sundae in one sitting. After a while, you don’t even taste it.

  3. In the end, the point isn’t even to “know Italy.” It’s to know yourself. That’s what travel—real travel—gives you: a chance to know who you really are and what you’re made of. Without the plushy upholstery of comfort and familiarity, you begin to see. You find out what you’re good at and what you’re not good at. What you’re passionate about. Who you are when the chips are down. Travel is the only thing you buy that makes you richer. Great things never come from comfort zones.