How to Plan the Perfect Trip to Italy

You don’t just go to Italy — you surrender to it. Cobblestone alleys that twist like secrets, lemon trees that scent the breeze, old men in piazzas arguing over espresso strength — Italy doesn’t ask for your attention, it demands it.

From Roman ruins to Tuscan hills and Amalfi coastlines sharp as love letters written in ink and sea spray, Italy is less a destination and more a carefully staged seduction. And like any romance, the magic is in the details. Which is where this guide about how to plan the perfect trip to Italy comes in.

Time your Italy trip right, or miss the magic

It’s important not to simply pick a date for your trip to Italy, but to plan it carefully with the season in mind.

High season in Italy, running from mid-June to late August, brings peak crowds and sweltering temperatures across the country and significantly higher prices for transport and accommodation. In summer, Italian cities like Rome and Milan are often overcrowded with tourists but largely deserted by locals. If you plan to visit Italy in summer, follow the locals and head to the seaside to cool off, rather than focusing on sightseeing in the big cities.

The shoulder season is an excellent time for a trip to Italy, with fewer tourists, pleasant temperatures, and a beautiful golden light. It’s the ideal moment to enjoy Italy’s urban delights, while not too early or too late in the season to hit the beach or go hiking. In May, spring flowers are in full bloom, while October marks the beginning of the truffle season. If you’re into skiing or relaxing by alpine fireplaces, January is a great time to visit the Dolomites.

According to ISTAT, Italy’s national statistics institute, tourism peaks in July with over 20 million overnight stays, while in May, it’s closer to 13 million — a significant difference in the number of visitors per square meter of Italian soil, which says it all!

Pick your spots, but don’t pick too many

A rookie mistake made by first-time visitors to Italy is trying to see everything. Yes, you can technically plan Rome, Florence, Venice, Milan, Naples, Cinque Terre, and Sicily into a two-week Italian itinerary, but that wouldn’t make for a relaxing trip, and you’d miss out on the relaxed lifestyle Italy is famous for.

Remember that visiting Italy isn’t a cardio exercise. It’s a country to be savoured rather than rushed through. It’s best to pick 2 or 3 regions at most when planning a 2-week trip to Italy. You can, of course, mix things up by combining a northern region like Veneto, a central one like Tuscany, and a southern one like Campania, giving you a balanced diet of history and culture.

An even better idea is to base yourself in one place for a week or longer. From there, you can use trains or a rental car to explore the surrounding sights. Florence, for example, makes a fantastic hub, as there’s just so much to see in Tuscany alone, from cities like Pisa, Lucca, and Siena to the rural vineyards and peaceful abbeys.

Tip! To make your trip go smoothly and you will not be distracted by calls at an inconvenient moment, use the call recorder app iPhone. Firstly, Call Recorder will allow you to fully maintain contact with the outside world, but not be distracted from important things right now. Secondly, iCall ensures that you do not forget important details of the conversation and can confirm what you said verbally.

Book smart and select the right accommodation

Skip the big chain hotels with lobby jazz music and go for something more local. Agriturismos (farm stays), boutique B&Bs, and even monastery guest houses provide character, local flavours, and often better pricing. Plus, there’s nothing like waking up to a rooster crow and a nonna’s homemade fig jam. When you plan your trip to Italy, consider these options for a more authentic experience!

Tip: In peak months, book 2–3 months in advance. In the off-season, it can be worth to wait, as you will likely find some great last-minute deals. Websites like Agriturismo.it or local booking platforms often offer more unique accommodation options than mainstream sites.

Language and etiquette: Know the basics

There’s no need to be fluent in Italian when you visit Italy, as you’ll get along perfectly fine with just English. But leaning a few Italian phrases? That can be molto importante – very important!

It’s considered polite to say “buongiorno” (good morning) when you enter a shop or to say “permesso” when squeezing past someone in a crowded space. Never order a cappuccino after 11am. unless you want the barista to curse at you behind your back. Italians are warm but proud people, and a little respect goes far.

Especially in the south, the Italian language is accompanied by hand gestures known as “gesticolare”. You’ll see them everywhere and may feel tempted to copy them, but it’s best to resist doing so as an outsider. Doing so could make you look foolish and even lead to unintended mistakes. If you must try, it’s better to wait until you’re not at the dinner table with a family from Naples!

The trains, the planes, and the scooters

Italy boasts an excellent train system, with the national railway company Trenitalia and private high-speed operator Italo offering fast, reliable, and comfortable trains across the country. For example, a high-speed train from Rome to Florence takes just 90 minutes, which is even faster than flying when you factor in the time spent getting to the airport. Regional trains are cheaper and slower, but they can offer more scenic routes.

To get the best price, book in advance online. Keep in mind that seats on high-speed or InterCity trains during peak season can sell out quickly if you book last-minute. Tickets for regional train services can be purchased on the spot, as they have fixed prices and never sell out.

If you’re heading somewhere rural, like exploring Sicily, renting a car is a wise choice. However, it’s important to know that Italian drivers are confident, or rather, aggressively efficient, so try to anticipate their moves when driving. Be warned that finding parking can be a nightmare not only in big cities but also in small towns popular with tourists, like Varenna on Lake Como during summer. Riding a scooter in cities like Rome or Naples is best left to locals and daredevils.

The great diversity of Italian cuisine

Italian cuisine is incredibly diverse and much more than just pizza and pasta. Even these two iconic dishes have numerous regional variations that are completely unique. Eating pizza in Naples will ruin all other pizzas for you, forever. Pasta isn’t the same everywhere either. Enjoying Cacio e Pepe in Rome is an entirely different experience from having Pesto Trofie in Liguria. It’s essential to learn about the distinctive local dishes in each region of Italy and to ask what’s in season.

A good tip to remember is that lunch is typically the main meal of the day in Italy. Dinner matters too, but it’s usually eaten much later in the evening. And don’t forget about aperitivo hour, between 6 and 8 pm — a cultural ritual in itself, with drinks and snacks serving as a warm-up before the main event.

Pack light, pack right

The cobbled streets of Italian towns can be brutal on suitcase wheels, especially those with four wheels. It’s often wiser to bring a backpack or a soft-sided trolley bag with just two wheels, which handle the rough terrain far better.

Italians dress sharply and with style — especially in cities — so if you plan to go out, it’s best to dress up for the occasion. That said, comfort is important too, so make sure to pack good walking shoes, as you’ll almost certainly be doing a lot of walking during your visit to Italy.

Remember to cover your shoulders and knees when visiting churches or other religious sights. Also be aware that in many Italian cities, the police can hand out fines for dressing inappropriately — for example, walking around without a shirt, which is only acceptable at the beach.

Unexpected costs, surprises, and joys

A trip to Italy will almost always cost more than you initially planned, whether it’s the coperto (a cover charge of usually €1–3 per person) at restaurants, or the extra drinks you end up ordering at yet another irresistible outdoor café with a view. Tipping isn’t mandatory in Italy, but rounding up the bill is always appreciated, and leaving a tip when sitting down for a meal at a restaurant is likewise a good idea.

Budget travellers should take note that many museums offer free entry on certain days — usually the first Sunday of each month — so with some research, you might be able to save quite a bit.

Sometimes, the best part of the day won’t be on your itinerary and won’t cost you a thing. A street musician in Verona. A cat sleeping on a warm Vespa in a Sicilian alley. A quiet conversation with a shopkeeper who says his olives taste like his grandfather’s hands — rough, salty, proud. Or simply sitting with a cheap beer bought from the supermarket on the seaside promenade, watching the sun set across the sea.

Final thought: Let go, a little

When you plan your trip to Italy, remember that your itinerary shouldn’t resemble a checklist, but rather follow a rhythm — one that allows for spontaneity, slow moments, and unexpected joys. Italy is a place where trains may arrive late, yet an espresso at the bar always comes quickly. You might spend an hour inside a wonderful church you stumbled upon and forget all about the museum for which you needed to queue for three hours in the blistering sun. It’s good to have a rough plan, but never let it dictate your days like a command, as that’s just not the way to properly do a trip to Italy.

The perfect trip to Italy starts when you stop rushing. When you miss a turn and discover a trattoria where the chef is also the waitress and her dog takes naps under your table. Make sure you plan a bit, yes, but also be open to the beautiful chaos. It’s Italy, after all!