5 Mistakes to Avoid When Planning a Trip to Italy


Almost everyone who I’ve ever met or known who has visited Italy absolutely raves about their experiences— the people, the food, the wine, and the sights. I typically nod in agreement while the usual places are listed, or sometimes chime in with the things that I also love about traveling there.

However, after years of operating our small group tours and customized private trips in Italy, I’ve come to understand how to get the most out of your visit to this beautiful country, and also a few common mistakes made by travelers that can be easily avoided for an even more amazing and unique experience during your vacation.

Here are 5 common mistakes that can keep you from the authentic and unique experience you’re looking for on your Italy trip (and what to do instead!):

1. Eating only at places with menus in English

Yes, there are great restaurants that have menus in English. But the real adventure begins when you’re in a place so authentically local that they are not catering at all to travelers, even if they know they could make more by having a menu that travelers could understand.

2. Eating “Italian Food”

There’s no such thing. Italy is all about regional cuisine—what you eat in Naples should be very different from what you eat in Milan. Eat the local dishes that are specialties of that region so you can taste what they’re best known for, and enjoy each dish at its very best.

3. Waiting for the bill to come

You’ll be waiting forever! (As long as you’re in an authentic place.) This isn’t a huge mistake, but it is a helpful tip! Restaurants in Italy aren’t trying to rush you out the door, they’re not solely focused on turning tables. So they often won’t bring your check until you ask for it.

4. Taking a huge tour with 20+ people

With this size of group you just can’t have the intimate, authentic experiences that allow you to see Italy as it should be.

We see these 30+ traveler groups all the time. They eat at the worst restaurants because that’s where they can get reservations for that size, they shuffle through the streets having sights pointed out to them, without going in and experiencing anything unique. And they have tour guides who are ticking off a checklist of things they’ve seen.

Get intimate! If you are going to take a tour, focus on small groups, experiences, and places that take you behind the scenes and not through the main thoroughfares where everyone else is walking.

5. Being afraid to get off the beaten path

Albert Einstein said, “the definition of insanity is doing the same thing over and over again, but expecting different results.” But I’d like to add that my definition of insanity (applicable to this situation, at least) is going to the same exact places all the tourists go, and expecting a unique and authentic traveling experience.

Traveling to Italy is about having a deeper understanding and appreciation of the culture, history, and their way of life. Yes, for some folks it is just as important to see Botticelli’s Birth of Venus at the Uffizi Museum. And that’s ok (because it’s amazing, of course!); but if you’re in Florence and all you do is stay in the historical center of the town (as many tourists do) then you are swimming in the sea of other visitors where there are certain establishments (and many vendors) who are catering simply to the tastes of tourists and not the reality of the locals.

Venture to the Oltrarno (the other side of the river) where more Florentines live and work. Stroll the streets and get lost. Find a café or a restaurant that has a small menu, only in Italian, and try it. Get outside your comfort zone. Go to a place where they don’t speak any English. Learn a few phrases in Italian and maybe mess up your order trying to use them (it’s all about the experience!).

Traveling is Truly What You Make of It

Traveling in Italy can be nearly like a “Disneyland experience” —manicured, swimming with the sea of other tourists, comfortable, and accessible.

Or you can get your hands dirty, explore, and absorb the culture like a true local.

If the latter is a little scary, or uncertain, or you’re not sure where to start or how to go about it, then join us on one of our curated culinary trips to Italy where we help facilitate bridging that gap.

We’ll introduce you to our friends—locals who live and work in the places we visit—who show us the inside scoop. We’ll teach you a few Italian phrases, or help with your ordering if you’d like some help. We’ll give you a behind the scenes view at artisan workshops, crafts that have been passed down through generations, and homes where you can dine with locals. And as always, our small group tours stay within 6-12 people to allow for more intimate experiences. (no 20, 30+ groups here!)

We’re taking two more trips to Italy this year—September & October— and we still currently have a couple spaces left in each of them.

Learn more about our 9-day Heart of Italy Tours (and why they are an experience of a lifetime) here.

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4 Not-to-Miss Restaurants in Italy


“Wait…this is fresh made pasta, right?” I asked as the server shot me a look of severe discontent. 

Since when did I become such a pretentious eater that boxed pasta seemed so abhorrent?  Oh…since spending 3 weeks gorging myself in Italy, scouring the country for the best eats. I had officially been ruined for all the Barillas & DeCeccos of the world. After witnessing Italian nonnas (grandmas) fresh rolling pasta in the back of restaurant kitchens and lingering over fragrant sauces it was no wonder I was appalled by food from a box and a jar!


After settling for his unequivocal reply of, “yes.”, I took a deep breath, a sip of wine, and replayed my trip through Italy as I prepared for my last meal before jetting off. As an avid traveler Italy was one place I had been hesitant about visiting…not because I was concerned that I wouldn’t like it, but because I was concerned I would love it too much and never want to leave.

And boy did Italy live up to all the expectations in my mind. From the first peek of the rolling Tuscan countryside through the airplane window, to the thrill of riding on a scooter around winding cliff side roads on the Amalfi coast, to this quaint little restaurant in Florence where I was eating my final fresh pasta dish, Italy took my breath away around every corner.


There is something so special, so enriching, so passionate, so simple about the way Italians live. And food is a major part of that beautiful life. On my first night in Italy I made friends with a group of locals who invited me over for a barbecue. I stood awe struck in their Renaissance-period kitchen as one of them nearly apologized to me because, “this olive oil isn’t very fresh…it’s nearly 8 months old since their family is preparing for the olive harvest this year.” Old olive oil?! Is that even a thing?! At home I just used whatever EVOO I could find in my cabinet, purchased from who knows where, who knows when. And that was just the beginning of my education in the way Italians eat, drink, love, and live.

One of the most beautiful things about Italian cuisine is how utterly simple most of the dishes are and that so much of the rich aroma and flavor comes from using very fresh ingredients. Italians are not shy about their pride in this matter. While participating in a cooking class the chef looked at me and matter-of-factly asked, “Do you like lemon thyme?”  Then he continued by saying, “Great, let’s go pick some,” as we trotted out of the kitchen where a few pots of fresh herbs grew. I felt like smacking my Staples’ ‘that was easy’ button

As a tour operator for international culinary trips, my sole purpose in Italy was to uncover the places that made me feel uniquely in love with Italian cuisine…places that I would be overjoyed to share with other like-minded food lovers. With some help from my friends at Utrip I was well connected with local Italian experts who showed me the way. And amongst some of my favorite meals were these 4 gems I highly recommend you check out:

  1. Fried Pizza at La Masardona in Naples


2. Fried (you’re noticing a theme…aren’t you) Calamari Salad at Ristoteca Oniga in Venice


3. Cacio e pepe at Cacio e Pepe in Rome (seems legit, yes?)


4. Arugula salad & tagliolini magnifico at Trattoria Gargani in Florence


Do you have any “must-not-miss” places you’d recommend? I’d love to hear them! Drop me a comment — I’m always looking for new great places to be able to direct clients to (and eat at myself, of course!).

You can always find more of my “must-not-miss” places ON our actual small group tours to Italy and other destinations. Check ‘em ouuuut!

Don’t forget to pin this post for easy reference!


(A similar blog post was originally published by our friends at Utrip on their blog. Utrip is an online travel planner that uses your interests and budget to sort through millions of options to deliver you a personalized itinerary in minutes.)