Interview with WhyGo Italy Expert Jessica Spiegel

Santa Maria Novella
We’ve been reading travel writer Jessica Spiegel’s informative articles on WhyGo Italy for quite some time and had the pleasure of getting to meet her last summer in Rome. It seemed only natural that we pick her brain for some of her fantastic advice on travel in Italy and share it with our readers. Jessica first visited Italy in 2001 and though she is currently based in Portland, she is in the process of finishing up paperwork to make a permanent move to Italy. We asked her to share a little bit about how she got started with writing and what advice she would give to travelers. Check out part one below and come back tomorrow for the last part of our chat.

Tell us about your history with Italy. What drew you to wanting to share your knowledge and love for the country with travelers?

It used to be that whenever I visited a new place, I’d fall completely in love with it. I was an Anglophile after studying in England in college, and a Francophile after chasing the Tour de France around in 1999. But when I first went to Italy, the country lodged itself in my heart and didn’t let go. I’ve traveled to other places since that trip, but I’m still an Italophile. I just can’t get enough of Italy.

I started working for BootsnAll in 2006 answering phones and selling Eurail Passes, that kind of thing, because it was a local (Portland) company working in travel – I just wanted to be involved somehow. About six months into my job, my boss said, “Hey, you like to write, don’t you?” I jumped at the chance to start writing on BootsnAll, and asked them to set up an Italy-specific site for me while I was at it. I wrote on WhyGo Italy in my spare time, just for fun, for seven or eight months before it became part of my job.

After my first trip to Italy, I started getting asked to help friends plan their Italy trips – so WhyGo Italy is a natural extension of something I enjoyed doing already. My goal with the site is that readers feel like they’re getting travel advice from a friend – it is, after all, the same advice and tips I give my friends and family.

Also, it kind of breaks my heart when I hear people talk about a recent trip to Italy and what a bad time they had. If I can help people avoid the pitfalls that could lead to an unpleasant trip, that’s a good thing.

What is the most common mistake you find that readers make when planning their trips to Italy?

I think most of the mistakes people make, whether it’s regarding travel or not, have to do with expectations. Set your expectations appropriately and you’re in a much better position to enjoy whatever it is you’re doing (or at least be prepared for whatever could be problematic).

With Italy specifically, the way this comes up over and over again has to do with the perception people have about how easy it is to get around the country. I routinely get emails from people saying, “I’ve got five days in Italy – I know it’s not much time, but I’d like to see Venice, Florence, and Rome, with maybe a side trip to Pisa and the Cinque Terre. Is this possible?” I’m exaggerating for emphasis, but not by much. I’m constantly amazed at what people think is reasonable. My first piece of advice in every single one of those cases is the same – look at a map. I honestly think people don’t realize how far apart, say, Venice and Rome are – nor do they bother looking up travel times. They just assume that since Venice, Florence, and Rome are the usual big three stops on an Italian trip that they must be pretty close together, or that traveling the number of miles that separate Venice and Florence will take the same amount of time that those miles would take where they live.

Sure, Italy isn’t a big country, and technically you might be able to set foot in Venice, Florence, Rome, Pisa, and the Cinque Terre in the space of five days… But if that’s the kind of trip you want to take, I’m not sure I’m the best person to talk to for advice. That’s not traveling to me – that’s some kind of race – so I’m likely going to try to talk you out of your hectic schedule.

What’s on your “to-do” list when you visit the following cities: Rome, Florence, Venice, and Naples?

What’s on your “to-do” list when you visit the following cities: Rome, Florence, Venice, and Naples?
One of the top things on my to-do list anywhere in Italy has to do with food – finding a few good spots to eat that don’t have menus translated into six languages and serve what’s considered local specialties. Another thing I like to do, and something that sometimes becomes a necessity for my own sanity, is to find the “quiet corners” in any city. In the bigger touristy places that’s often both more challenging and more necessary. Increasingly, re-visiting places I’ve been to before also means catching up with friends, which is always a delight.

Specifically for each of the cities you listed:

•Rome – I head for the Trastevere as soon as I can. Rome kind of overwhelms me, and in the Trastevere I can pretend it’s a small village again, if only briefly.

• Florence – A tour of the city’s gelaterie is always on my to-do list in Florence; I have to stop in at my favorite one (Festival del Gelato) and then I try to discover a few new ones each trip.

• Naples – If all I have time for in Naples is eating pizza and wandering aimlessly in the historic center, that’s okay with me.

• Venice – I wish my to-do list in Venice included “buy an apartment and move there,” but until it does I’ll stick with my favorite thing to do in Venice, and the thing I tell everyone they absolutely must do in order to have a chance of loving the city – get good and thoroughly lost.

Of course I have recommendations of what to do in each of those cities if you haven’t been to them before, including the big sights and attractions along with some people may not be as familiar with. I’ve written many articles about the Top 10 things to do in different Italian cities.

Check back tomorrow to read the second part of our interview, where we’ll find out about Jessica’s dream trip to Italy and what the best resources are for planning your next trip.

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