Why Take a Guided Tour to Italy? (5 Good Reasons You'll Love it)

Raise your hand if you know someone who’s been to Italy.
Raise your hand if you know someone who wants to go to Italy.
Raise your hand if you yourself have been or want to go to Italy.

We’re going to guess you raised your hand (mentally) at least once, if not all three times.

To say Italy is a popular vacation destination would be an understatement. With 63.2 million tourists a year (2018), stunning Mediterranean coastline, imposing mountain ranges, Roman artifacts, rich history, and world-renowned art, fashion, and cuisine, it’s no wonder Italy ranks as the 5th most-visited country in the world.

So if it’s so accessible to that many travelers per year, WHY should you take a small guided tour to Italy as opposed to just planning the trip yourself? What do you get from a hosted tour that you wouldn’t on your own?

Well, well, well, we’re so glad you asked.

On our Heart of Italy Tour, we strive to bring you the absolute best Italy experience you can’t get anywhere else, no matter how hard you Google, or how many travel books and travel blogs you read.

So here it is. Here’s why it’s definitely worth it to travel to Italy on a small guided tour. This is what you wouldn’t get on your own.

1. Connections with Locals

For a popular destination like Italy that can easily be researched online and that you’ve inevitably had a friend visit before, in a few keystrokes or text messages you can find recommendations for a nice hotel, a decent restaurant, and logistical information like where to go, how to get there, where to capture the best picture, etc.

But the one thing that can’t be replicated or transferred is relationships.

We believe you can only really understand a place through connection with its people, which is why our trips are centered around the relationships with local friends we’ve built over the years. Friends that you’ve also met and cooked with in our virtual cooking classes.

In Italy, we introduce you to so many of our local friends who have a passion for where they grew up and live: the neighborhood cheese maker, Benedetto; Chef Alain, an amazing pasta chef who is ready to teach you his tricks; Roberto, a pastry baker for over 60 years who still enjoys letting us come into his kitchen to peak behind the scenes.

In Florence, one of the most tourist-heavy places in the country, our friend Gaia gives us an intimate insiders’ view of the city, sharing her personal stories with the local artisans she introduces us to in the neighborhood where she lives.

It’s the personal relationships that make an experience truly meaningful and memorable, and in Italy, our friends very quickly become your friends.

2. Unique, Non-Tourist Experiences You Simply Can’t Find on Your Own

Like we mentioned, many people have been to Italy. In fact, even some of those who come on our Heart of Italy Tour have been to Italy before.

But what they hadn’t experienced before were the unique moments we create for our travelers, like dining in Marika’s back patio with magnificent views and the freshest food picked literally right out of her garden. Like walking through local lemon groves and making limoncello from the lemons we pick off a tree. Like a pasta-making lesson from a local chef in a private Tuscan villa.

One of our travelers mused that he didn’t think he would have any way of relating to his friends’ or coworkers’ experiences in Italy, because his was far different:

“How can I feel commonality with Joe when he raves about the restaurant he went to, when I had dinner in Gloria’s home, overlooking the Duomo in Florence, helping her prepare pesto in the kitchen and listening to stories about her family business? It’s just a totally different side to Italy than seeing sites as a tourist.”

And that’s our goal - to show our Heart of Italy travelers a completely different side to Italy than they would be able to see and experience on their own.

3. No Stress, Absolutely None

How many hours have you spent researching and deliberating over the best hotel in the right neighborhood? Or what type of transportation to take from point A to B? Or which 4.5-5 star restaurant on Yelp is really the most authentic, or what experiences are really worth the splurge, or how much do you need to tip (wait, do you even need to tip? And when?), and where actually can you find the best pizza in Naples??

Relax. Close out of TripAdvisor and your fifty open tabs, we have you covered.

We’ve been there, we’ve put the hours of research in—not just online, but on foot. We’ve already visited all the best boutique hotels, we’ve already tried all the pizza in Naples, and we’ve already arranged the cooking classes worth doing and the boat trips worth taking.

No more research, no more deliberating, no more, as one traveler put it, fighting with your wife on a random street corner over where to eat dinner.

He says it typically goes down like this: “I Yelp, she Googles. My friend recommended this restaurant, her friend recommended that one. Eventually, we’re lost, hungry, frustrated, and ready to settle for the next place we see.”

No more settling or being unsure of anything. We pick you up from the airport. We handle all cash and tipping. We make all reservations and payments.

We handle all the stressful parts of travel so that you can just be present and fully enjoy your time abroad.

4. Delicious Meals, Every Time

We do not believe in wasting a meal on a “so-so”, or even a “pretty good” option. Our philosophy is you only have a few precious days on your trip; you deserve to eat and drink the best of the best!

With us, you can be assured that we’re sharing our absolute favorite places—not just the ones your cousin recommended because she stumbled into them starving after a failed Google search on a random street somewhere. No, goodness, no.

We have vetted and refined our list. We taste and taste and taste (it’s a hard job, I know), over and over and if something doesn’t meet our standards anymore, we replace it with a more delicious experience.

We dine at a restaurant with seafood caught by a fishing boat that just came into port. We lunch in a private plant nursery on multiple courses made from their garden. We watch our pizza being fried (yes, you read that correctly, we’re talking fried pizza, friends) before our eyes. We sip on wine made from the vineyards surrounding our table and carefully paired with each dinner course.

Rest assured every meal will be regional, local, seasonal, and fresh. We only choose places where we want to eat—because, after all, we’ll be eating with you!

5. Long-Lasting Friendships

I’ll be honest, one of my (Annie’s) biggest concerns when I started these tours was: what if people don’t get along?

Well, my biggest worry turned into what I’ve enjoyed the most in what we do.

Over the years, we’ve witnessed a sharing of experiences, joy, laughter, and depth of conversation that has brought our travelers together.

We consistently have “reunions” with travelers who want to get together again, and often there are travelers who arrange to visit each other in their hometowns after our trips are over.

There’s a bond created among our groups from experiencing something special together. After each trip, we walk away with friendships with people across the country (and across the world) that we cherish and want to nurture.

The experience we provide on our Heart of Italy Tour is truly like none other. Don’t just take it from us—read the reviews and testimonials from past travelers.

We’ve already taken the time to plan your dream trip to Italy that will save you countless hours of stress and planning, that will have you feeling like a VIP, and that will give you a view of Italy that is more than just checking “places to see” off a list.

We’d love to introduce you to our friends in Italy … your vacation is ready and waiting.

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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 big tour busses here!)

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If you’re traveling to Italy on your own and don’t know where to start or want to tap into our travel expertise to make the most of your trip, check out our customized travel coaching and optional booking service.  

Learn more about our 9-day Heart of Italy Tour and why it is an experience of a lifetime.

No matter where you travel, we always recommend purchasing travel protection to safeguard against sudden changes or cancellations. If you don’t already have a preferred vendor, you can check out ours - Travel Insured - which offers a “Cancel for Any Reason” policy. 

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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 awestruck 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

If you’re looking for more recommendations, you’re in luck! Check out our Florence City Pocket Guide for the best of the best.

And if you want to taste the fresh pasta for yourself (and make some!), join us on our Heart of Italy Food Tour where we eat our way around the country.

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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.

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