Practical Italy: 5 Things to Consider When Planning a Trip to Italy

Not Just Another "Dolce Vita"Before you know it, “travel season” will be upon us. Planning a trip to Italy? Before you book, make sure you take a look at these things to consider when planning a trip to Italy. Keep in mind that Italy doesn’t work like Canada or the US or England or really, like anywhere else, so the more thought you put into your trip, the better.

1. When are you planning on going? Your experience will differ depending on when you travel to Italy. I’d say anywhere between May – September would be considered high season. Prices of everything will be at their peak, lines will be longest, temperatures will be warmest, and beaches will be the most crowded, especially in August. For many things, it would be extremely wise to book ahead (everything from tickets to the Coliseum to hotel reservations) and pay the small booking fee that accompanies such things in Italy. Trust me, the few euros you spent booking your tickets is so worth it when you pass by all the poor schleps standing in line under the blazing Roman sun to get a glimpse at the Coliseum. With your pre-reserved tickets, you’ll breeze right by and into the Emperors’ playground senza problemi.

Looking for a calmer time? Try October or April, but be sure to avoid Easter.

Cinque Terre-10

The Cinque Terre beaches in August.

2. What are you planning on doing? Italy offers something for everyone, in my humble opinion. But I’d say it’s best (especially if you’re travelling in high season) to figure out exactly what you want to do and where you want to do it, in order to make sure you have the best Italian experience possible. I’m not saying jam-pack your trip full of things and run around with a never ending ‘To Do” list, but have an idea of what there is to see and where you can see it. Don’t go to Florence if you think you want Roman ruins, and don’t bother with the Cinque Terre if you’re looking for the Renaissance.

Then, if your top thing to do in Florence is “sample as much gelato as possible”, there’s no need for heavy planning, except for maybe mapping out a few gelaterie. But if you just have to get in to see the David, and walk the Vasari Corridor, and take a painting class, and visit Santa Croce, and catch a game of Calcio Fiorentino, you need to get your organizational skills out and do some planning.

Many things are closed on odd days of the week and can have interesting hours, reservation policies, dress codes, etc. Best to do your homework in advance, then there won’t be any surprises eating up your precious time in Florence.

The Boot

The Boot

One more piece of advice: Don’t go somewhere just because you’ve heard the name.  If you’ve heard of Pompeii but you don’t know (or care) what happened there, then don’t go! The Travel Gods will not thunder down upon you. This is your trip, and the only person you have to please is yourself. Who cares if all the guidebooks say to go there? If you don’t have any interest in a place, don’t waste your time and money on it.

Detto questo (that said), don’t forget to be open-minded too. 

3. How are you getting around? Oh, you’ll just rent a car in downtown Rome (horrible) and go for a toodle up to Tuscany (hilly) then drive over to Venice (islands), maybe through the Alps (scary roads) and swing ’round to the Cinque Terre (carless), zip down to the Amalfi Coast (horrifying roads) and land back in Rome, all in your little Fiat 500.

Will you? And it’ll go well for you?

No, it won’t.

Well, at least, probably not.


Italian cities and towns are home to many a Zona Traffico Limitato (ZTL) or traffic limited zone. That means you, cruising around in your cinquecento, are going to be collecting a lot of traffic tickets for driving where you’re not allowed to drive. That’s one thing. And they chase you at home with those traffic tickets. (On a recent trip to France, I got two, so I should know!)

Now add the fact that most Italian cars are equipped with a manual transmission (you’ll probably pay a premium for an automatic), and are much smaller than our North American counterparts, and you’ve got a couple little speed bumps that you weren’t really counting on. I’ve seen families have to change their rental cars because all of their heaps of luggage doesn’t fit. People stall out in parking garages and roll down those rolling hills of Tuscany because they thought they could easily master driving a manual car in one go. And forget parking – it’s like an Olympic sport in Italy. You won’t get a spot close to where you need to be, and many hotels in city centres don’t have parking because of the blasted ZTL.

Loaded with luggage

Loaded with luggage

Solution? If you’re going from major city to major city, use the train. Italy is much better connected than Canada (and I assume the US) when it comes to trains, both high speed and milk run. They often come right into the centre of town (where you’ll likely be staying) and can be fairly comfortable. A car in any major city centre (and some smaller ones too) will only cause you extra headaches. I promise.

That said, there are some parts of Italy (the extreme south) that are just better visited with a car. I understand that. It will just take more planning on your part to make sure you don’t run into (m)any disasters.

La Stazione, Milano

La Stazione, Milano

4. How fast are you moving? My dear friend and I did a whirlwind 6-city-8-day trip around Italy a few years ago. Even though we were in our early twenties, hitting up beaches and taking the train, it was exhausting.

I advise you to take it easy and add in lots of leeway for things to go wrong (which they almost always do in Italy). Trains don’t run on time, reservation times are really just a suggestion, you will get lost in Siena’s labyrinthine streets and a disgruntled Venetian waiter will point you in the wrong direction when you’re lugging your suitcases around in the blazing July heat. (More about that later).

Travel guru Rick Steves always says to plan your trip as if you’re sure you’ll be back so as not to pack your schedule too tight. That way you can have the time you want to do some of the things you want (not all), but you’ll do them well and be satisfied with the experience. The last thing you want is to have a meltdown at a museum because the long line means you’re running 20 minutes behind your colour-coded schedule.

Additionally, try to minimize your one-night stops in places, and mix in easy days of staying in town with longer days of side-trips and excursions. Plan time just to walk around, nap (there’s no shame in it) or just lounge around reading a book and sipping prosecco. This is all part of the Italian experience too!

5. What’s your budget? I’m all for thrifty travel, but penny-pinching has its downsides too. High-rollin’ it all the way around The Boot might not be your best option, either. The moral of the story? Be realistic about your budget expectations. With the Internet, information about what pretty much everything costs is at your fingertips. Again, do your research so you won’t have too many surprises. You can find meals, accommodation, transportation and things to do in just about every price range, if you dig around a little.

A final word to the wise about money: If you’ve gone all the way to Italy, do the things you need to do (and therefore spend the money you need to spend) to enjoy it. It’d be mighty disappointing to want to climb the cupola of St. Peter’s in Rome but not do it because you think it costs too much.


A Nocturnal Foray to the Farmacia

Not Just Another "Dolce Vita"Summer. 2013. Rome. Sometime after midnight.

A knock at the door.

I jolt awake and stumble to open it. I’m not tipsy, just tired. I’ve been shepherding university students around Rome for a week. Enough said.

A gaunt, tired-looking one-such-student greets me from the other side of the threshold. She’s leaning against the door frame, one hand on her stomach, looking just about as displeased to be waking me as I am feeling at having been woken.

“Darcy, hi. What’s wrong?” It’s not a stellar opening line, but it’s all I can manage, squinting into the light of the hotel hallway.

“I’m sick. I’m going to the pharmacy. I just thought I’d let you know.” Her voice is a whisper.

“What time is it?” I ask. Then I realize it really doesn’t matter. “Just a sec. I’ll come with you.”

“If you want. You don’t have to.” Yeah. Right.

“Yes. I want. Wait here.” I return to the welcoming darkness of my room and grope around for the light switch. I quickly find the clothes I had been wearing the day before, grab my purse and pull my hair into a semblance of a ponytail. Back into the hallway I go. Darcy seems to have worsened in the 2 minutes that have passed.

On our way to the hotel lobby, she tells me her ailments: upset stomach, headache, diarrhoea, aches, pains the usual. Of course, she hasn’t brought any medicine with her from Canada and of course, I’m not legally allowed to give her anything. That leaves the pharmacy.

I call a taxi and we wait outside. At least it’s warm. But it’s Rome, on a weeknight, at some little hour of the morning. What pharmacy is going to be open? This is Italy, after all. I pray the taxi driver will know, because I don’t. I don’t let Darcy know this though. Nope. Me, I’m cool as a cocomero.

Soon enough, a taxi pulls up and the driver greets us through mouthfuls of potato chips. “Ciao belle, dove andiamo stasera?” Hi beautiful girls, where are we going tonight? 


We get in. After a brief conversation between the driver and I, we decide to go to the Farmacia on Via Nazionale, because it’s one that’s supposed to be open 24-hours a day. I’m skeptical, but keep my mouth shut and employ  my lips to shoot a reassuring smile at Darcy instead.

We turn onto Via Nazionale, which, by day, is hustling and bustling. In the middle of the night, it’s a different story. We don’t pass another car. Don’t see any pedestrians. My hope of a 24-hour pharmacy dwindles. My patient starts to grow carsick, but seems to ever have faith that there will, indeed, be a Shopper’s Drug Mart-like haven of medicine waiting for us down the darkened Via Nazionale. I have to tell the driver to go more slowly to help Darcy keep her dinner down. I curse myself for not thinking to bring a plastic bag and make a mental note to always keep one in my purse in future.

Finally, the green LED cross, symbol of the farmacia all over Italy, comes into view down the street. I’m still skeptical. All too often the light’s on and nobody’s home.


The driver pulls up to a darkened storefront and executes a relatively smooth stop. (Bravo). My heart sinks as I look at our destination: doors closed, barred security screen locked in front. It’s not open, I tell him. You have to ring the buzzer, he replies good-naturedly. I tell him I’ll take his word and pay him our fare. He drives off into the night, but not before offering us some of his potato chips. We decline.

I survey the deserted street, all the while trying to look confident for my ailing student. Sure, this is no big deal. Sure I’ve done this before. Sure, this is normal.

[No it’s not, the Canadian in me screams. The Italian in me shrugs.]

Feeling oddly like I’m on a movie set, and worrying that something terrible is about to happen (cue scary “don’t do it” music) I approach the door and ring the buzzer with trepidation. Within 5 seconds a light in the back of the store comes on. A curly-headed guy in track pants and a tshirt approaches the doors scratching his head. The glass doors slide open and he appraises us through half-closed eyes. Surely this can’t be the pharmacist. He looks to be about 18. And yet it seems to be.

“Cosa volete?”  he grunts through the security screen. What do you want? 

Ahh, a charmer.

I respond in an equally abrupt manner and explain my student’s symptoms and the type of medicine we need. I wait for him to open the screen and let us in. Instead, he takes a long look at us, steps closer to the screen and looks up and down the street. Seemingly satisfied, he turns away and shuffles back into the store.

Can’t we come in? I call after him, curious about all the cloak-and-dagger stuff.

No, is his reply.

Why not?

Because too many people steal drugs at night.

Oh. Well then.

Soon enough he’s back with a little rectangular box. He slides it to me through the bars of the screen and stands with his arms crossed while I check it out. There’s no brand, no pictures, no niceness, just a long medical name I wouldn’t recognize in English or Italian. 

I ask the price. It’s surprisingly cheap. Darcy looks at the medicine, shrugs and says she’ll try anything. She hands me money sits down on the sidewalk.

I pay Mr. Charming. He starts to wave us away. I ask for a receipt and foil his plans of going back to sleep 30 seconds earlier. 

He reluctantly goes back to the back of the store and rings one up for me.

All of this is done by passing money, medicine and receipts through the security screen. It feels more than a touch clandestine. Again, I’m waiting for someone to yell “cut!” and for our scene to be over. Or for some drug thief to make his grand entrance.

We thank him. He dismisses us with a wave as he disappears into the back of the store. As if by magic, the glass doors close again, and we’re left to find a taxi back to the hotel.

And that, ladies and gentlemen, was my nocturnal foray to the farmacia.

[When I asked some Italian friends if this type of thing was normal, they agreed. I then had a similar experience at a Florentine farmacia late one Friday night where money, medicine and receipts were slid back and forth in a little metal box through a hole in the wall of the store. Orders were yelled through a pane of opaque glass.]

Summer Event: Siena and Stars

Not Just Another "Dolce Vita"Siena, the perfectly preserved medieval city I’ve come to think of as home in Italy, is hosting a series of great events this summer between 10 July and 2 August, called  Siena and Stars. I don’t usually write about events on here, but for this one, I just couldn’t resist.

You can reach the Siena and Stars website by clicking on their logo below but since the webpage is mostly in Italian, I thought I’d do you a favour and let you know what Siena and Stars is all about.

Screen Shot 2013-06-25 at 6.10.15 PM

Taking place in Siena’s Piazza del Duomo against the stunning backdrop of Siena’s gothic cathedral, the organizers of Siena and Stars have put together a line up of not-to-be-missed performances of all kinds. From pop, to jazz, to opera, to ballet, to theatre, Siena and Stars has something for all tastes and price ranges.  Count on 10 – 60 euros per ticket, depending on the event you’re looking to attend. Not bad!

Siena is a wonderful place to visit no matter what’s going on, but for anyone who is venturing to Tuscany this summer, I’d recommend mixing it up with the locals at one of the Siena and Stars events. It’ll be a taste of Siena and Italy, at their best. Plus, you’ll be visiting this place:

Siena Skyline

Siena Skyline

A few event highlights:

July 10 – Marco Mengoni in concert

July 14 – Tango with Miguel Angel Zotto

July 19 – Buena Vista Social Club Orquesta in concert

July 21 – Mario Biondi and Pino Daniele in concert

July 25, August 1 &2 – Siena Jazz Concerts

For more information and a full listing of the events, visit the website at or call +39 0577  280 545. Email enquiries can be directed to, while tickets can be purchased online at or by telephone at + 39 055 21 08 04.

Buon divertimento!  Have fun!