Help Me Help You

You’re coming to Italy and want advice? Great, I’ve got some—but it might not be what you’re expecting.

Country drives, street art, frescoed palaces, natural beauty—Italy has it all. Photos mine.

Cari amici,

It’s a perfectly reasonable thing—travelers to Italy, whether first-timers or not, turn to locals for sightseeing tips, itinerary ideas, restaurant go-tos, and so on. Knowing this happens, I’ve started dumping my recommendations into city- or region-specific files so I don’t have to start from scratch every time I get an inquiry. Often an itinerary requires a more personalized response, but I can’t do it alone. There’s a right way and a wrong way to ask for trip advice, and I’m pleading with you, in my best Tom-Cruise-as-Jerry-Maguire imitation, to help me help you.

You see, even if I know you, I’m not a mind reader, and I’m likely not to remember how many times you’ve been to Italy, where you’ve been, and how long ago that was. For example, when good friends were coming to visit me, one of them, a newbie to Italy, put visiting an Etruscan necropolis at the top of her list—an interest I wouldn’t have known about, even after decades of friendship, if she hadn’t told me. If I don’t know you well, or at all, I have no idea what might ring your bell, and I’m not particularly eager to spend hours compiling maybe-it’s-useful-but-who-the-hell-knows information for you. All of which is to say you shouldn’t do the following.

1. Tell me you’re arriving in, say, Rome, and ending up in Venice, and what should you do along the way?

Well. There’s a lot of Italy between those two points, and it’s filled with charming and/or eccentric villages, museums both massive and niche oriented, churches and monasteries, vineyards and frantoi, agriturismi and hole-in-the-wall hotels, artisans’ workshops and high-end shopping, evocative ruins, and spectacular parks, lakes, mountains, and beaches. To [ahem] name a few options.

I need details. What do you like to do? What are you dying to see? Is your priority visual splendor or gastronomic delight? Do you want to buy pottery, or maybe see it made? Dream of quiet nights in a tucked-away village where you can chat with the owner of the lone restaurant over glasses of house-made limoncello? Prefer to window shop or lighten your wallet where fine leather goods or designer fashions are sold? Do you love baroque architecture? Hate cathedrals? Please, give me something to go on!

2. Fail to say whether you plan to travel by car or train (or both).

There are advantages to both modes of travel, but depending on what you want to do and where you want to do it, one or the other will make more sense. A jaunt between major cities and well-serviced towns is best done by train if you aren’t hankering for an agriturismo stay or a meandering countryside drive with spontaneous stop-offs. But if you don’t tell me what you’re thinking, I can’t play devil’s advocate. Sure, it might end up being cheaper for a group to travel by car, but have you considered the challenges and costs of parking? Have you thought this through? I have no clue.

3. Don’t tell me when you’ll be traveling or how long you’ll be here. When I ask you, ignore my questions.

Because sure, my recommendations are carved in stone no matter the season or proximity to major holidays, local festivals, and Italian holidays you’ve probably never heard of. (If that sentence looks a little blurry, blame the dripping sarcasm.) I beg you, please don’t tell me you’ve decided to go to Florence for Christmas and it’s now mid-November and you want to hit all the major sites but you only have three days and you’ve made zero reservations. I do have advice for you, but at this point it’s completely useless. No, wait, here it is: don’t bother coming.

4. Don’t suggest making the slightest effort to get together even if you’ll be fairly close by.

After all, your time is precious. Never mind that I’d appreciate the thought even if it doesn’t pan out.

5. Don’t thank me.

Let’s have an email exchange in which you tell me little, I ask lots of questions to narrow down the type of recommendations that can help you, you fail to answer my questions, I do my best to give you some ideas, and then poof! You disappear without a word. That makes me feel so very warm and fuzzy and not in the least bit used. However, being only human, there’s the tiniest chance I’ll ignore you the next time you hit me up for advice. Just saying.

Despite my sarcasm and snarkiness, I’m not bitter about these requests nor angry with the requesters. (Well, okay, I am a bit huffy about no. 5.) What I am is flabbergasted. People who do this must be close relatives of the people who write this kind of thing in expat groups and forums: “Hi! I’m moving to Italy in two months!!! Where should I live?”

I really want to help you enjoy Italy, I do. So think ahead, do a little homework, choose your adventure, then ask for help, specific help, and preferably not at the eleventh hour. I’ll even hop in the car or take the train to rendezvous with you if the timing works out and your travels will take you within a couple of hours of Perugia.

Tante belle cose. Alla prossima—

Cheryl

© 2023 Cheryl A. Ossola

Books of the week (a selection from my bookshelves, and yes, I’ve mentioned some of these before):

• Florence: A Map of Perceptions by Andrea Ponsi (delightful, with watercolors)

• Rome in Detail: A Guide for the Expert Traveler by the staff of the Italian supplement of the International Herald Tribune

• Walking Between the Tiber and Lake Trasimeno: 30 Itineraries Through the Landscape of Memory by Louis Montagnoli and Giannermete Romani (have I done one of these walks yet? No.)

• Venice: The Enlightened Traveler’s Historical Guide by John W. Higson, Jr.

• The City of Falling Angels by John Berendt (essential reading)

• The Stones of Florence by Mary McCarthy (the large-format edition with photos will save you from having to google every place and piece of art she mentions)

• Venice Observed by Mary McCarthy (again, the large-format edition with photos)

P.S. My book! Which you can buy here or on the usual sites, or, better yet, order if from you local bookstore. Another fab option is to ask your library to stock it. If you read it and like it, please tell your friends and/or leave a few lines of praise on any bookish site. You’d be surprised how much a rating or review helps authors. Baci!