Whether you’re coming to Italy for the first time or returning for more, it’s important to set your expectations. While Italy is not a massive country, it’s also not a tiny one. Italy is shaped like a long boot, meaning you must travel up and down rather than in a circle. The distance can make reaching everything you want to see a bit challenging.  

As we frequently see people making this mistake, we created a guide that walks you through every step of planning your trip to Italy. It’s a simple approach that will help you make the most of your time in Italy and actually enjoy it.

Step 1: Decide where to go

With so many offerings, deciding what to see and do in Italy can be overwhelming. Depending on how much time you have, you’ll likely not be able to visit everything you want on one trip. Sure, you can book a whirlwind tour of Italy that takes you through all the key places in a week, but you won’t appreciate it all as you rush from place to place.

Northern Italy

The north of Italy is where you’ll find the fashion capital of Milan, the alluring canals of Venice and the charming Italian lakes and stunning mountains. It’s a great place to explore any time of the year, but it’s even more magical in winter. If you’re into skiing or any outoor activities, then visit the Dolomites. Lake Como and Lake Garda are perfect destinations for outdoor lovers and culture buffs as they offer a blend of ourdoor activities and charming towns with loads of history.

If you’re into urban adventures, go to Venice and partake in the Venetian carnival or learn about the glass blowing production of Murano glass. Milan is where you’ll find the famous Duomo di Milano and Leonardo da Vinci’s The Last Supper.

Central Italy

Central Italy is home to the most visited regions. Tuscany and Lazio attract the most visitors, with Florence, Rome and Cinque Terre topping everyone’s itinerary. For culinary adventures, head to Bologna, Parma or Modena in Emilia-Romanga, a region famous for food. Follow in the footsteps of the Etruscans and the Renaissance in Tuscany and Umbria.

Rome, of course, is Italy’s main attraction, with layers of history visible all over the city. From ancient Roman sites to Baroque churches and Piazzas, it’s a must-see destination for culture buffs. Head to Marche, Abruzzo or Molise for some seaside breaks and outdoor adventures.

Southern Italy

Southern Italy is the home of the Amalfi Coast, pizza and stunning beaches. In addition to the bustling streets of Naples, Greek and Roman ruins and volcanos, you’ll find a slower pace and warmer weather. Don’t skip Italy’s islands of Sicily and Sardinia for a taste of a different side of Italy.

Don’t miss the wonders of Matera in Basilicata, the sunny beaches of Puglia and the scenic drive through Calabria. Other than a few touristy places, this part of Italy isn’t as widely explored by North American tourists. Take advantage of that and discover new places to love.

Step 2: Decide when to visit

Deciding when to visit should be a critical part of planning a trip to Italy, as it can affect prices and availability. You must also consider the seasons, as each offers a unique perspective on Italy’s charms.

• Spring (March to May): This is a great time to plan a trip to Italy. The weather is mild, although it might be more rainy, which makes it more comfortable to explore. You also get to experience booming flowers and Easter celebrations. While crowds are thinner than during summer, prices start to climb as the season progresses.

• Summer (June to August): If you’re considering planning a trip to Italy during summer, keep in mind that it’s the most expensive and crowded time to explore. The temperatures are often uncomfortably hot, which makes exploring less enjoyable. In August, many Italians take their vacations, so businesses could be closed, and you’ll have local tourists to add to the international crowds. This is the perfect time for hitting the beach and long evenings on the patio.

• Fall (September to November): Fall is our favourite time to travel, and it’s an ideal time to visit Italy. The weather is comfortable, as you’ll still get plenty of warm and sunny days with some rainy ones. There are many festivals happening at this time, including truffles, chestnuts and mushroom festivals. You’ll also encounter smaller crowds and lower prices than in the summer.

• Winter (December to February): When planning a trip to Italy, you should definitely consider coming during the winter months. You can go skiing in the north or enjoy milder weather in the south with plenty of sunny days. Cities are not as crowded and you can enjoy major sites with fewer crowds.

Step 3: Set a budget for your trip

Many people ask us if Italy is an expensive destination. While the cost of living here is much lower than in Canada, the cost of vacationing will depend mainly on where you go and what you do. When you travel and how long you’ll stay will also play a role, which is why budgeting is an important part of planning a trip to Italy.

Daily costs can vary widely depending on your travel style. What can be expensive to one person will be cheap to another. If you’re on a budget, you can get by on €50-€80 per day (for a couple) for meals and activities. If you’re in the mid-range, you should plan for €80-€200. Luxury travellers can expect to spend €200 or more per day, depending again, on where you’re going and what you plan to do.

To maximize your budget, book your flights and accommodations well in advance. Use comparison sites like Skyscanner to find the best flight deals. For a unique and cost-effective accommodation experience, look into agriturismos (farm stays), which often include meals.

Getting lunch at a local market instead of sit-down restaurants, or making your own meals is a great way to save money. You can also take advantage of free museum days, which are offered on the first Sunday of each month. Taking advantage of city cards/passes is another way to get discounts at local attractions, trasit and restaurants.

Step 4: Book your flights and accommodation

As you plan your trip to Italy, booking your flights and accommodation early can lead to significant savings. Consider flying into major hubs like Rome or Milan, then using trains to reach your other destinations. You can use budget airlines like Ryanair or EasyJet to save when travelling within Europe.

When it comes to accommodation, you’ll find a wide range of options to suit every budget and preference. Hotels range from budget to luxury and are often centrally located, making them convenient for sightseeing. Airbnb can be an excellent choice for longer stays or group travel, offering the chance to live like a local. For a uniquely Italian experience, especially in the countryside, consider staying in an agriturismo. These charming farm stays often offer home-cooked meals featuring local produce. If you prefer staying in hostels, you’ll find them mostly in major cities.

Step 5: How to travel around Italy

Once you arrive in Italy, you have to figure out how you’re going to get around. Travel within Italy is relatively easy, as there is an extensive transportation network. Trenitalia and Italo both offer high-speed and regional services at competitive prices. You can take high-speed trains between major cities or buses to smaller cities without train connections.

Within cities, you’ll find a mix of buses, trams, and, in larger cities, metro systems. Purchase tickets at tabacchi shops or newsstands before boarding, and remember to validate your ticket in the machine on the bus or platform to avoid fines. Many cities also offer bike-sharing programs, providing a fun and eco-friendly way to explore.

Driving is our favourite way of seeing Italy. With a car, you can explore rural areas or destinations with limited public transport. However, be prepared for narrow streets in historic towns and a more aggressive driving style than you might be used to. If you’re planning to drive, ensure you have an International Driving Permit if your license is from outside the EU.

Step 6: What to pack for Italy

Packing is an critical part of planning your trip to Italy. You don’t want to overpack, as you might regret it later. Many towns have narrow, cobbled stone streets and stairs that make dragging your suitcase to your lodgings a nightmare. The last thing you want to do is carry a heavy suitcase up the stairs in the heat. It’s not fun.

Start with comfortable walking shoes, as you’ll likely be exploring on foot while in Italy. When visiting churches or other religious sites, it’s important to have modest clothing that covers your shoulders and knees. Make sure to have a scarf or a sweater if you plan on visiting places of worship like the Vatican. Remember to pack adapters for your electronics, as Italy uses 220V electricity.

For summer trips, pack light, breathable clothing, a sun hat, and plenty of sunscreen. For winter trips, bring warm layers, a waterproof jacket, a scarf, and gloves, especially if heading to the northern regions. You might also consider an umbrella or a rain jacket in case it rains.

Step 7: Book in advance

We always recommend that you book your tickets ahead of time. This doesn’t just apply to flights—popular tourist attractions book up, and you need to get your tickets ahead of time to avoid disappointment. Italy is a popular destination with many historic sites, and some places have a limit on how many visitors can enter each day.

Recommended attractions to book ahead

One of the best ways to ensure you see the sights is to book an organized tour. Tour groups often get to bypass the line, and some tours even offer early or evening access away from the crowds. Another bonus is that you’ll have a guide who can explain what you see and its importance.

Final checklist

• Before you set for Italy, make sure that your passport is valid for at least six months beyond your return date.
• It’s a good idea to get travel insurance in case things go wrong.
• We often email copies of important documents to ourselves as a backup, but you can always print them out and store them seperately from the orignals.
• Don’t forget any necessary medications and prescriptions.
• Double-check all your reservations for accommodations and pre-booked attractions.

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