Visiting Italy for the first time has long been on your bucket-list. Now that you’re finally planning the Italian vacation you’ve dreamed of, you want to have the trip of a lifetime. After spending hours DIYing it on TripAdvisor, searching for last minute deals, watching YouTube videos, practicing Italian on Duolingo, and incessantly Googling Italian customs, you finally board the plane. 

Only to end your trip feeling exhausted and like you need a vacation from your vacation. Disappointed, this was not the Italy you expected. An entire trip of being just another number on a big bus tour, waiting in long lines under the hot Italian summer sun, hopping trains, and eating subpar meals. You left Italy feeling duped! Instead you wanted to experience the real Italy, that many travelers, who visit Italy multiple times, never experience in their lifetime. 

Having been in your shoes. Doing “all things” and visiting “all the places” you’re told to see on your first trip to Italy, I too was left wanting more. That’s why after years of living as a local in Italy, and planning seamless trips that help food and wine lovers experience Italy like a local, I have put together the nine most common mistakes that people make on their first trip to Italy – so you don’t have to!


#1 Booking too many activities in one day

Although it may be tempting to jam-pack as much as possible into your first trip to Italy, this can leave you exhausted and disappointed in your overall experience. 

You’ll make the best memories in your trip’s small, spontaneous moments! While it can be beneficial to loosely plan your days to ensure you hit all the locations you wanted to see, we’d recommend planning for some downtime to soak in Italy and see where your days take you. 

Click here to uncover first time Italy itineraries that are the perfect blend of free time, activities & great food and wine!

first trip to italy itinerary

#2 Thinking that renting a car is cheaper than the train

Traveling by car can be scary or convenient in Italy, depending on how adventurous you are! But no matter which bucket you fall into, certain aspects will make car travel more costly than expected.  

For example, if you want to take Italy’s Highway, the autostrada, you’ll need to factor in all the toll costs and the extra time you may need to spend in line to pay for those tolls. If you decide you should rent a car, read our guide to driving in Italy here


#3 Not realizing that Italy is a long country

Most major cities in Italy are connected by superfast trains. But fast trains won’t necessarily solve your problems! Many first-time travelers don’t realize the sheer length of Italy and think they can get by spending a day in Rome and quickly popping over to Venice the next day! 

Italy is a long, skinny country, and the time between Italy’s most touristy cities is A LOT longer than most travelers expect. Especially when you factor in travel time, the stress of possible strikes, and potential train delays. While you want to experience Italy in one trip, this can be a recipe for vacation burnout. If you want to return home relaxed from your Italian vacation, you’re better off choosing a few cities as your home base.

first trip to italy itinerary

#4 Traveling only by train

Sure, you can get to most of the well-trodden tourist cities by train, but if you want to experience Italy like a local and get off the beaten path, you’ll need to rent a car at the very least. 

Many places, such as Ascoli Piceno, are most easily reached by bus rather than train. And don’t worry, contrary to popular belief, there is air conditioning and stops along the way! 

When you travel only by train, you’ll waste unnecessary hours instead of using your precious vacation days, immersing yourself in the local culture.

Pro-tip:  Get out a map and look at where the cities you want to visit are located, and then check both train and bus schedules to find out the best option to get from point A to B.

Don’t want to stress about logistics or lingo on your first trip to Italy? Click here to discover all the ways you can experience Italy like a local & take the guesswork out of your next Italian Vacation. 


#5 Waiting until the last minute to book your tour

Waiting until the last minute to get a deal sounds like a good idea, right?! WRONG! These days, small boutique tours operators like The Italian On Tour offer bonuses and discounts only once a year when they launch their tour dates.

Want to get the best price of the year on your first trip to Italy and access fabulous bonuses, like FREE room upgrades? 

Click here to download the Italy Insider’s Guide today! 

Once you join the mailing list, you’ll get access to our best travel tips and be the first to know when we drop new tour dates, which will allow you to book your trip with us at the best price and scoop up fabulous bonuses! Psst! You’ll want to get on the list as bonuses are ONLY available once-a-year!


first trip to italy itinerary

#6 Forgetting to check when Italians take their National holidays when planning your first italy itinerary

Italians love a National Holiday! Because of this, most of Italy shuts down during these periods. If you’re unaware of when the holidays are before you travel, you may arrive frustrated to find restaurant, shop, and museum closures that can make a real dent in your first trip to Italy. 

One of the biggest holidays in Italy is Ferragosto which is on August 15th every year. Ferragosto is one of the busiest and most expensive times to travel to Italy. When you’re trying to book your travel plans, you’ll compete with foreign tourists and all the Italians that take a vacation this time of year.

Pro-tip: Skip the Ferragosto and finish Italian summer vacation well before the August 15th rush hits.  Click here to discover your perfect Italian summer tour to avoid the crowds and wasting your precious vacation time melting in sweaty line-ups!

#7 Dressing inappropriately

You don’t want to feel completely out of place or embarrassed in a foreign country because you’re unaware of social or cultural norms. Being a country of Catholic origins, many of Italy’s most famous monuments are churches that you will not want to miss out on! 

Stunning Basilicas like the one in Loreto, one of Italy’s Largest Pilgrimage sites, welcome over 1 million pilgrims annually.  You can visit when you join us on Italy Undiscovered or Italy’s Epicurean Journey. Click here to find out more about these trips!

To enter, you’ll need to cover your shoulders and wear shorts/shirts that hit below the knee.  

Pro-Tip: In the summer, pack maxi dresses that can be layered with a light cardigan to cover your shoulders. 

first time trip to italy itinerary and tips

#8 Spending too little time in one place

Constantly unpacking and repacking your bag is stressful for many travelers and can be a significant time suck that you could otherwise spend making lifelong memories. You don’t want to spend half your trip worrying whether you’ve left behind your phone charger or your favorite sweater at the last location! 

You’ll also find that you never truly experience the joys of local life in any one location. 

That’s where The Italian On Tour steps in. When you join us on tour, on your first time Italy itinerary you’ll unpack just once! 

Staying in one place allows you to soak up the local Italian atmosphere and get to know the community’s residents. After your trip with us, you’ll leave your vacation feeling relaxed and grateful for your time on tour instead of returning more stressed out than before!

Ready to relax, recharge your batteries, and enjoy the perfect amount of activities and free time on your next trip to Italy?

Click here to discover your next Italian vacation today!

first trip to italy itinerary

#9 Underestimating the total time it takes to plan your trip to Italy

Whether it’s your first trip abroad or to Italy, it’s a big decision and an investment of your money and time. 

You could easily spend hours on travel forums and your hard-earned dollars on purchasing guidebooks only to be led astray and end up having a stressful, unfulfilling Italian vacation.

Knowing where to find reliable information is a great start, and that’s why we’ve put together our FREE Italy Insider guide so that you can avoid the Top 10 mistakes even the smartest travelers make on their trip to Italy. Click here to download it now!

Pro-tip: Seek advice from someone on the ground who knows Italy like the back of their hand. Travel advice from an inexperienced local or an agent who only visits Italy once a year won’t always offer you the inside look into Italy to plan the Italian vacation you’ve been dreaming of.

Instead, you need someone who can translate the Italian experience, and according to Forbes, that is exactly where The Italian On Tour steps in!

Click here to discover how we can help!



first time trip to italy travel tips



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