Are you finally ready to start planning that dreamy bucket-list Italian adventure? Maybe you’re thinking of Rome, Venice, Milan – or Sting’s Villa in Tuscany, featured in the latest issue of Conde Nast! In reality, many of these locations only have a good reputation because of their notoriety amongst tourists and celebs. But, the drawback is that tourists make destinations, you guessed it – touristy! Do you really want to experience Italy sitting on a bus with 50 other people? Fight crowds for half of your time in Italy? Eat greasy, tasteless, or oversalted subpar food with poor service?

Deep down most people want to experience the real Italy – not just the Italy that’s been marketed to you. When all you see is Tuscany, Rome, Florence, Venice, Sicily, Milan, and Cinque Terre (oh yeah, and the latest being Puglia!) – it’s hard to know where to even start!

Having made those mistakes (so you don’t have to) after traveling Italy for over 40 years combined, we’ve put together the Ultimate guide for How to Plan a Trip to Italy. Whether you’re dreaming about rolling hills, sprawling vineyards, and shimmering blue oceans without the crowds, but aren’t sure how to get there, we’re here to help!

How to Plan a Trip to Italy – Without the Crowds

Choose the experience over the destination

It’s not your fault that what immediately comes to mind when you think of Italy are some of its most famous and touristy destinations! Do you want the truth on why they are so popular? 

Popular destinations in Italy, like Rome, Venice, Tuscany, or the Amalfi Coast, spend the most on marketing to place themselves front and center, drawing the attention of travelers like yourself, writers and TV personalities that amplify the notoriety of these “dream destinations.”

Reality Check: If you want an authentic experience in Italy, focus on the experience you want to have. Don’t visit Sting and Trudie’s Villa in Tuscany just because you saw it in the latest issue of Conde Nast! If you want to truly experience Italy, you’ve got to get off the beaten path, and no, we don’t mean following Stanley Tucci’s trail across the Bel Paese. Stanley Tucci never made it to Italy’s Hidden City, Ascoli Piceno, the most underrated in the entire country!

Bottom line, don’t plan your trip based on the destinations you see plastered all over social media, televisions, or magazines. Doing this usually results in disappointment, long line-ups, and needing a vacation from your vacation. But don’t dismay! The Italy you’re seeking still exists – you just have to find it! If you don’t have time to waste researching and going down the google spiderweb, then you’ve come to the right place! When you join us on tour, you’ll take the guesswork out of your next Italian vacation, all while finally experiencing the real Italy that so many people who travel to Italy multiple times, never experience in their lifetime.  

How to Plan a Trip to Italy – Without the Crowds

Book your tours & experiences first

Now that you’ve chosen how you want to experience Italy, your next priority should be actually booking those experiences. Whether you’ve chosen to sit back, relax, and let The Italian on Tour take the legwork out of experiencing Italy like a local on your next trip to Italy, or you have hours to research and DIY your itinerary, the first thing is to figure out is what tours you want to do in Italy. You’ll want to put this at the top of your list, as exclusive tours or curated experiences, like what we offer on your trip with The Italian On Tour, simply aren’t available year-round and can’t be created only for two people. To ensure you don’t miss out, you’ll want to know the availability and dates to put in your vacation request pronto and grab your seat before your preferred travel dates are SOLD OUT!

How to Plan a Trip to Italy – Without the Crowds

Get your vacation approved 

Retired? You can skip this step – woohoo! As soon as you’ve made your deposit and have your tour dates set in stone, request those dates off of work immediately! You don’t want an unexpected scheduling conflict to get in the way of you and your dream Italian adventure. That’s why when you book with The Italian on Tour during our yearly tour date release, you have a 7-day zero-risk guarantee! This means you can put down your deposit worry-free, knowing that you have seven full days to cancel and get your deposit back during the yearly tour launch. 

guide to planning a trip to italy without the crowds

Have pets or kids?

Whether you have fur babies or little humans at home, you’ll need to find yourself a sitter or family member to help out. You’ll probably be able to entice them to help you with some Italian cheese, wine, or leather goods! And don’t worry – on your tour with us, we’ve got you covered with visits to award-winning wineries, multi-generational cheesemakers, and local artisans. At these locations, you can purchase direct and fill your suitcase with souvenirs and gifts that you, your friends, and your family will actually enjoy and use. Because let’s be real, nobody really wants another tacky fridge magnet.

planning trip to italy

Buy travel insurance

Yes, you need travel insurance for Italy! Even in a relatively safe country like Italy, things can (and do!) still go wrong. Travel insurance will protect you from unexpected delays, cancellations, medical emergencies, and more. 

Better yet, buy cancel-for-any-reason travel insurance. Cancel-for-any-reason is highly recommended by most insurance companies and typically must be purchased within 14 days of booking your tour. This policy will protect you from any hiccups out of your control, like flight delays or cancellations, illnesses, or family emergencies. 

These days, a simple flight delay of a few hours can put a major dent in your travel time by making you late for a connecting flight or missing a tour. We’d recommend planning to arrive a day earlier than any booked tours begin, which will put your mind at ease. By arriving early, you can ensure a smooth meet-up with your tour and get the added bonus of working off that jetlag before it’s go-time! 

Want to know which insurance company you should choose? We recommend World Nomads! Need more information before making the purchase? Read more about Travel Insurance in Italy HERE!

How to Plan a Trip to Italy – Without the Crowds

Decide on additional destinations 

Whether it’s your first trip to Italy or one of many, you probably have a list of places you want to visit. Just 3 hours from Rome and a short train ride from Venice, numerous first-time and seasoned travelers join us on tour each year because they want to experience the real Italy and still see the iconic sites they’ve read about in the history books. When you book your trip with us, we’ll help you find the best way to connect with your tour or next destination! 

how to plan a trip to italy guide

Traveling in the Fall & Spring months is not a fool-proof method to escaping the crowds

By now you’ve probably read an article or two about traveling in the low or shoulder season to escape the crowds, only to not be told that many of the touristy destinations like Venice practically have no off season.  With Carnevale in full swing during February, and numerous film festivals throughout the year, places like Venice have done a good job of making sure there are always tourists in town. Thinking of Amalfi or Cinque Terre in the Fall? Well, the fact is, a lot of these seaside towns shut down when the summer crowds simmer out, leaving few options for places to eat and limited facilities open that normally attract visitors during the high season. 

Looking for the best beaches to escape the crowds in Italy? Click here. 

how to plan a trip to italy

Be realistic with your time

Ever felt like you need a vacation from your vacation? Those whirlwind big bus tours where you unpack and repack every night are a recipe for major burnout. With limited vacation days, you want to make the most of it! That’s why we recommend at least 3 nights in each location. A vacation spent on trains and buses is really no vacation! Sightseeing becomes a total blur when you have to constantly worry about if you’ve checked everything off your bucket list and if you accidentally left your toothbrush behind at your last hotel.

On your tour with us, you’ll enjoy the added bonus of unpacking just once! Giving you a chance to truly relax while enjoying the perfect amount of curated experiences and free time on your Italian vacation.

How to Plan a Trip to Italy – Without the Crowds

Start checking flights

Check flights as early as you know your travel dates to Italy. Most airlines release flights one year in advance. Buying early is often the best way, and although deals can be found close to your dates, this can be a bit of a gamble. You don’t want to miss the tour of a lifetime because you couldn’t find a seat on a flight!

how to plan a trip to italy without the crowds

Book train travel

Train tickets are generally released six to seven months before your travel dates, so there’s no need to worry if you don’t see tickets available when booking your trip far in advance. 

We highly recommend booking your train tickets as soon as they’re available, especially for popular and high-speed routes between major cities, such as Rome to Milan, Bologna to Milan, Naples to Rome, or Florence to Rome. These high-speed train routes can get fully booked in Italy, so booking well in advance is extremely important near the Italian holidays as trains book quickly with Italian locals and tourists competing to book their train travel during these peak times. 

Want to learn more about Italian Train Travel? Read How to Travel by Train in Italy – A Local’s Guide HERE!

how to plan a trip to italy guide

Put in your restaurant reservations

Italians tend to always reserve and never just show up, with the exception being a bar (don’t know the difference between an Italian bar and a bar in the US and Canada – click here to find out!), so don’t be caught off guard if you’re asked if you have a reservation.  You’ll definitely need them, especially on the weekends and in cities like Venice and Florence. Have you been eyeing some Michelin-starred restaurants? These often require a credit card to secure your reservation and with celebrity chef status driving up the popularity you’re going to want to start booking these places 10 to 12 months in advance.

how to plan a trip to italy

What to do if your destination is not reachable by train

You’ve heard rail is the best place to travel across Italy, but we’re here to break that myth! Trains are great for city-to-city travel but a real stinker when it comes to visiting the interior, as the Apennine mountain range runs straight through the heart of Italy. 

To be able to hunt for truffles, visit some of Italy’s most beautiful villages, soak up the many national parks, and experience Italy’s most underrated cities, you’ll need to rent a car and have an actual map. Yes, it’s true; Google Maps can often be unreliable in Italy, too! Read up on driving in Italy HERE or recruit someone from the inside to help translate the Italian experience!

Now, you’re ready to plan that dream vacation to Italy! Unless you want to spend hours researching and Groupon-ing, you need the help of someone on the inside. That’s exactly where The Italian On Tour steps in! When you book a trip with us, you’re becoming part of the family. Support small businesses, connect with the locals, and visit the hidden gems you won’t see on TV! We’d love to have you join us on tour – choose your perfect itinerary HERE!

And don’t forget – grab your FREE Italy Seasonal Packing Guide, so you know exactly what to put in your suitcase for every season!



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