Tips for planning a trip to Italy: a step-by-step guide

Planning a trip to Italy is exciting, but with so much to see and do, it can also feel a little overwhelming. This beautiful country is overflowing with historical sites, incredible food, stunning scenery, and vibrant culture.

Your trip can be as relaxing or as adventurous as you want to make it. Whether you dream of gondola rides in Venice, exploring ancient ruins in Rome, or indulging in pasta-making classes in Tuscany - the key to a truly incredible Italian adventure lies in thoughtful preparation. And we’re here to help you with that!

You might also like these articles:

• Ultimate Italy travel tips for a seamless experience
• The Worldpackers Italy travel guide
• How to experience Italy through backpacking
  

Planning a trip to Italy step-by-step

Turning your dream Italian getaway into a reality doesn’t have to be stressful. With a little organization, research, and this guide, your trip planning will be easy. Follow these steps for planning a trip to Italy that you'll be able to look back on with a smile.

Deciding when to go

Italy has something to offer year-round, but the climate varies from region to region. Peak season is generally from June to August. This means that while you'll find sunshine and beach weather during those months, you'll also be facing higher prices for accommodation and flights. Plus, be prepared for crowds - lots of them.

If bustling tourist spots aren't your cup of tea, maybe look into the shoulder seasons - April to May or September to October. These times of year are great for exploring the outdoors because the weather is often still mild, but the crowds are smaller, and you'll usually find better deals.

For those who aren’t afraid of a little chill and some rain, consider Italy in the winter months. November through March offers the chance to experience a different side to Italy - quieter and more affordable.

Setting your travel budget

Italy isn’t necessarily a budget-breaker, but knowing how much you want to spend before you go is helpful for keeping things in check while you’re away.

One factor influencing your budget is accommodation. If you’re happy sharing dorms in hostels or staying in budget-friendly guest houses, you can expect to pay significantly less for a place to lay your head than if your preference is for luxury villas, for example.

If you’re trying to save as much as possible, or if you want to live an authentic, immersive experience, consider volunteering through Worldpackers. This platform allows you to exchange a few hours of work for accommodation and other perks, like meals and tours, in different parts of Italy.

Then, think about your food priorities. Do you imagine yourself dining out on fine Italian food and wine every evening? Or do you picture yourself picking up fresh produce from local markets and creating your own delicious picnics?

If you choose to stay in hostels or apartments or volunteer, you’ll often have access to a kitchen, which allows you to cook your own meals with delicious Italian ingredients.

The website Numbeo is a great resource for comparing the costs of everyday items, like meals in restaurants. On average, a three-course meal for two people at a mid-range restaurant is €60, while at a more affordable eatery, it will set you back €15.

Transport is another aspect to budget for. If you are thinking of whizzing between major cities on high-speed trains like the Frecciarossa - factor that into the budget now because those tickets aren't cheap. But booking early helps.

Buses and local trains can often be much cheaper but be prepared to add some extra time to your journey - although they are often quite scenic, so it might be worth it.

Italy’s public transport options can get you around pretty seamlessly. Some travelers even decide to rent cars, which lets you set your own schedule and provides the opportunity for some amazing road trips.

Just remember, though - if you plan to rent a car for your Italian adventure, you’ll need to factor in parking into your travel budget. Parking fees in Italian cities can add up faster than a speeding gondola. 

Also, look into whether or not you will need an International Driving Permit. In some cities, it might also be difficult to find parking spots, and we’ve heard of many travelers who got a fine for inadvertently parking somewhere forbidden, so beware.

You might also like: Explore Italy on the cheap: your guide to budget travel

Researching destinations

You'll likely hear these iconic cities mentioned often - Rome, Florence, Venice, and Milan. With good reason. Just thinking of them probably conjures up vivid images in your mind.

Think of Rome, and your mind probably flits to visions of ancient gladiators doing battle at the Colosseum, and if it’s not that, it’s the image of tossing a coin into the Trevi Fountain (after snapping a quick selfie first, obviously). For an unforgettable experience, you can even book a guided tour of the Vatican Museums or the Uffizi Gallery.

Then, there's captivating Florence - the birthplace of the Renaissance. Here, imagine yourself lost in the exquisite details of Michelangelo's David, or perhaps sipping on delicious, locally made wine as the Tuscan sun sets over rolling vineyards.

Then there’s Venice, with gondolas serenading you from below as you explore historic bridges. Picture yourself discovering secret canals, sampling unique cicchetti - bite-sized snacks designed to be paired with a refreshing glass of spritz.

Keep reading:

• Where to go in Italy: the best 20 places to visit from north to south
• The 20 best cities to visit in Italy
• The best 12 things to do in Northern Italy

Next on the list can be fashion-forward Milan. This stylish city serves up glamour by the bucket-load. From chic designer boutiques to trendy independent stores, prepare yourself for some serious style inspiration. Be sure to check out what's on at the Teatro alla Scala, one of the world's most famous opera houses.

If your travel wish list centers on quieter escapes off the typical tourist trails - consider looking beyond the well-known tourist hotspots to regions like picturesque Tuscany. You can delve into authentic Italy with its sun-drenched hills, endless vineyards, and charming rustic villages, and even stay in an Agriturismo.

If stunning coastal landscapes, colorful villages, delicious limoncello, and hikes with breathtaking views appeal to you, then be sure to factor in some time exploring the idyllic Amalfi Coast.

But if dramatic landscapes and charming villages speak to your heart more - The Cinque Terre might be your speed. This collection of five villages - built precariously into the cliffs and overlooking the sea - is famous for its network of walking paths and breathtaking scenery.

Defining your itinerary

Decided where to go? The next step for planning a trip to Europe is putting together an itinerary. Having a realistic plan ensures you're not wasting precious holiday time on travel days. However, try not to squeeze too much into your itinerary. The last thing you want to do is rush through breathtaking scenery without fully appreciating it all.

For instance, instead of trying to squeeze in both the Amalfi Coast and Cinque Terre, opt for one and truly immerse yourself in the experience. Slow down, savor the local delicacies, and connect with the culture at your own pace.

A basic 10-day Italy itinerary for first timers can be a starting point: start with the iconic trio - Rome (4 days), Florence (3 days), and Venice (2 days), and leave a day for traveling.

If you want to delve deeper into one particular region, a 7-day trip to either Tuscany or the Amalfi Coast would offer plenty of opportunities to experience the local culture and explore charming villages and coastal towns at your leisure, and you can spend the remaining time in Rome or Milan if your flight lands there.

To make your trip even more special, think about incorporating unique experiences, like wine tastings in Tuscany or cooking classes in a local's home. Many first timers fall so head over heels in love with this beautiful country that they book another trip straight away, to see and experience more.

Figuring out visas and other documents

First - check the validity on your passport and allow plenty of time for renewal if it is due to expire. U.S., Canadian, Australian, UK, and New Zealand passport holders can enter Italy and stay visa-free for 90 days within any 180-day period, so long as they have at least six months left on their passports upon arrival in the country.

If you are not from one of those countries, then visit your country’s foreign office website or local embassy well ahead of your departure date for specific guidance.

Apart from that, it is always a good idea to have travel insurance when traveling internationally, in case of unexpected events like medical emergencies or lost luggage.

Booking your flights

When comparing costs for planning a trip to Italy, look at flying into Milan instead of Rome as it is sometimes a much more budget-friendly option - and remember this when using online booking sites - turn incognito mode ON. Prices do fluctuate, so start doing your research as soon as possible and look for the best opportunity.

When choosing your flights, consider your priorities. Are you looking for the cheapest option, even if it means longer layovers? Or do you prefer a more direct route? Be sure to factor in travel time to and from the airport as well.

Looking for accommodation

Planning a trip to Italy offers several accommodation options, depending on your personal travel style and budget. You can use websites like Booking.com to book hotels, hostels and apartments, and take a look at Airbnb as well. 

If you’re up for a cheap and transformative experience, consider applying for one of Worldpackers many volunteering opportunities in Italy. We’ll talk more about that below.

Booking internal transportation

The next step is figuring out how to go from one place to another and booking some of those trips if needed – that depends on your choice of transportation means and also how strict your itinerary is. A website such as Rome2Rio is good to compare various transportation options, travel times, and costs.

As we mentioned, when it comes to domestic travel in Italy trains are one of your best choices. This is because Italy has an excellent, efficient (generally) and user-friendly high-speed rail system that conveniently links major cities like Milan, Florence, Rome, and Venice.

If you fancy hitting the road at your own pace, rental cars are available in all major cities. The benefit of having a car? Flexibility and impromptu stops at charming towns and viewpoints you randomly stumble upon along the way. 

Although this sense of adventure does come at the expense of searching for elusive (and potentially expensive) parking spots, so you do need to weigh that up and decide which style suits you more.

For those traveling to Italy on a shoestring - buses offer a significantly cheaper (although slightly less romantic) option than high-speed trains. Budget operator Flixbus serves hundreds of destinations in Europe and is popular with students and backpackers, thanks to its frequent discounts and unbelievably cheap deals. And there are also low-cost airlines, if you think of flying.

Booking tours and activities if needed

Italy boasts a wide range of organized tours and activities for all types of travel styles.For organized day tours, walking tours, cooking classes, or tickets to top attractions - consider using websites like GetYourGuide, which features free cancellation options.

For visiting popular places like the Vatican and some museums, you might need to book date and time in advance, especially during high season. If there are any attractions that you don’t want to miss, make sure you look into that.

Experiences over just checking off a list on your Italy itinerary

While you're exploring potential must-sees, keep in mind you can't experience everything Italy has to offer. But do try not to get too caught up in simply checking places off a list. What matters most is finding those special experiences you’ll remember long after you return home.

Is soaking up the atmosphere of a local piazza more your style, or maybe uncovering hidden vintage shops? Think about what truly interests you and prioritize those experiences.

Volunteering in Italy

One of the most enriching ways to experience Italy is by volunteering through Worldpackers. This platform connects travelers with local hosts across Italy, offering opportunities to exchange your skills for accommodation and other perks, and above all, a deeper connection with the country.

Whether you’re helping on a vineyard in Tuscany, assisting with eco-projects in Sicily, or working at a boutique hostel in Rome, Worldpackers allows you to immerse yourself in Italian culture while traveling on a budget. You’ll have the chance to work alongside Italians, learn the language, and participate in everyday life.

From cooking traditional Italian dishes to learning about sustainable agriculture, the hands-on experiences you gain through volunteering provide a unique perspective on Italy that goes beyond typical tourist activities. 

You’ll also get to meet other travelers, who might turn into travel buddies to explore the rest of the country together.

Additionally, volunteering gives you the flexibility to explore Italy at your own pace. With opportunities ranging from a few weeks to several months, you can tailor your experience to fit your travel plans. 

Hosts give you a few days off every week, and you’ll have insider tips on the best places to visit, eat, and explore, ensuring that your Italian adventure is truly authentic.

Check out some examples of Worldpackers positions in Italy:

• Get free accommodation in the Italian Alps, in the beautiful Vigezzo Valley
• Help out with daily activities and live in a hostel in Naples
• Live the Italian lifestyle in Verona, sharing languages with your hosts
• Enjoy nature and experience a simple and sustainable life in Cagliari
• Live on a sailboat in Palermo, Sicily

Want more? Click here to see all the opportunities currently available and save them to your wishlist or apply straight away.

You might also like our guide on How Worldpackers works, this article on Teaching English in Italy and this other one about farm stays in Italy.

FAQs about planning a trip to Italy

How do you start planning a trip to Italy?

Start with those crucial first steps - deciding when to go, figuring out how long you can go for, and then coming up with a rough budget. 

After that, it’s all about brainstorming destinations and must-do activities, like whether exploring ancient ruins and historical sites rank higher in your mind than strolling through picturesque villages and soaking up the scenery - then use that to start narrowing down regions that most align with what sets your soul on fire.

Booking accommodation and transportation early will be your best bet, especially in peak season (May - October). For a more local experience, consider staying in charming villages or towns that are less crowded, or volunteering in exchange for accommodation through Worldpackers.

How much does a trip to Italy cost per person?

You’ll likely pay between $100 and $200 per day on a mid-range budget per person for your Italian adventure (on top of flights). 

Of course, staying in luxury accommodation and eating in high-end restaurants will significantly impact those numbers. Equally, traveling like a backpacker or volunteering in exchange for accommodation lowers that cost.

Embrace local transport or hire a bike instead of taxis - every little bit saved is a little bit more you’ll have for eating out and experiencing this incredible country.

What is the best way to see Italy for the first time?

There is no definitive best way - it’s more about finding what suits your interests and budget best. A lot of first-time visitors opt to follow those iconic itineraries showcasing the ‘big hitters’ - Rome, Florence, and Venice - for a taste of history, architecture, and culture.

Others prefer basing themselves in a region - like dreamy Tuscany - for breathtaking landscapes, endless wineries, and laid-back vibes, while some people flock to Italy for its stunning coastline. This could mean exploring colorful coastal villages in Cinque Terre or those steep, dramatic cliffside towns dotting the Amalfi Coast, for instance.

Many first-time visitors don’t realize just how large Italy actually is, so trying to ‘see it all’ can feel incredibly rushed, leading to transport becoming a significant portion of your vacation. To make the most of your trip, consider focusing on a specific region or a few key cities that you can explore at a more leisurely pace.

Don't forget to venture beyond the beaten path and discover some of Italy's hidden gems. And if you have the time, volunteer for a few weeks or even months and get a true taste of what Italy is like.

Ultimately, planning a trip to Italy comes down to two key things - defining your personal priorities, then planning ahead to make it a reality. Once you're there, remember to be present, enjoy every single moment, and start planning your return trip straight away.