TripAnthropologist

The first time you plan an itinerary to visit Italy can be a little daunting but it’s where the fun begins! So let’s just step through it, one decision at a time. We’ll start by planning our bases and the number of nights in each base. Then we’ll add day trips, any tours or activities you’d like to experience. From there it’s on to transportation and accommodation and you’ll be on a magical Italy journey before you know it!

Step 1: Plan Your Bases

Traveling from place to place in Italy is easy with flights, trains, and buses in abundance, and ferries, taxis, and private transfers but each time to travel to new lodgings, you lose some of your day to traveling, checking in, and so on.

Traveling across Lake Garda, Northern Italy

This means that 3 nights is the minimum stay in one place that I recommend. So if you have 10 days, then three destinations are all I would be trying to cover.

If it’s not your first time in Italy, I suggest you get around the country a little less. I prefer to stay put and take a few day trips than be always packing and unpacking my bag.

The most popular Italian cities to visit are usually good bases for a week or more unless they are small villages.

Florence and Siena make good bases, for example, but San Gimignano and Pienza are not good bases unless you plan to drive around the countryside rather than visit cities.

If you are driving, then these smaller towns make lovely bases. If you’re relying on public transport, being on a train line is a real plus, and staying close to the train station makes a long day trip much easier.

Some of the most popular bases for a trip to Italy include:

Rome

Florence

Siena

Venice or Verona

Bologna

Sorrento

Palermo and Taormina

Step 2: Plan any day trips you’d like to take

Some of the most popular day trips include:

From Florence: Siena, Sam Gimignano, Pisa, Lucca, Cinque Terre, Volterra, Grieve in Chianti, Bologna

From Siena: San Gimignano, Florence, Montepulciano, Pienza, Montalcino, Monteriggione

From Verona: Venice, Lake Garda, Lake Como, Milan, Bologna

From Bologna: Ravenna, Parma, Modena, Ferrari, San Marino, Piacenza, Rimini, Florence, Venice, Verona

From Sorrento: Naples, Herculaneum, Pompeii, Capri, Positano, Amalfi, Ravello (and other towns and villages along the Amalfi Coast).

From Palermo: Cefalù, Agrigento/Valley of the Temples, Segesta, Erice, Monreale, San Vito Lo Capo

From Milan: Lake Como (Como, Bellagio, and Varenna), Lake Garda, Lake Maggiore, Verona, Venice, Florence, Bergamo, Pavia, Turin, Brescia, Verona, Genoa, Bernina train to Sankt Moritz, Cinque Terre.

Step 3: Plan your tours and experiences

Tours and Experiences are like mini-day trips that make sure you can see the most important sights, visit the places you’ve most wanted to see, and experience aspects of local culture that are sometimes the most memorable part of a trip to Italy.

*Lunch at the market in Florence, Italy*

Italian food is a vital part of the Italian way of life. Wine tastings, pasta-making classes, eating at a local’s home, and touring fresh food markets are wonderful ways to experience Italy and break up your days, forcing you to slow down and savor Italy.

It’s at this stage of the planning for your Italy trip that you run into hurdles – the cooking class you want only has availabilities on Wednesday, or the Vatican Museums are closed on the public holiday Monday, or it’s Milan Fashion Week and most accommodation is already booked.

This is when you rejig your itinerary to do the cities or the activities in a different order. It’s also why you don’t make bookings until you’re sure you’ve got everything in the right order.

Step 4: Plan your transportation

Getting to and from Italy is easy as you can catch a plane, drive or take a bus or train, and even a ferry. The cheapest city to fly into is Milan.

Venice, Rome, and sometimes Naples are almost as cheap as Milan. If you use Google Flights and put in your departure point and “Italy” for your destination, you’ll get a map showing the prices for each Italian airport.

Early morning at Milan Malpensa airport, Milan, Italy — *Early morning at Milan Malpensa Airport, Milan, Italy*

Once you’re in Italy, how you get around will depend on the part of the country you’re planning to travel through.

Buses are often cheaper than trains but high-speed trains are magic. Not quite as wonderful as train travel in Spain, but a lot cheaper!

Train and bus tickets are easy to purchase online and where possible, choose a ticket with a dedicated seat number or you might find yourself sitting on your suitcase between Milan and Lake Como as I did last summer!

Trains are air-conditioned and have buffet cars and toilets. What’s not to like?

Buses are the only public transport option in many parts of the country. For lakes such as Garda and Como, it’s usually faster to get a bus than a ferry and much cheaper.

*A bus along the Amalfi Coast road, Italy*

Ferries operate on the northern lakes but also to Sicily and Sardinia, Greece, and Croatia. Booking ferries online is generally not possible on the lakes, but is possible and recommended for all other trips.

Venice is a world unto itself. The train is much easier than the water taxi from Marco Polo Airport, and water taxis (vaporetta) are a brilliant way of moving around the island and to nearby islands.

Driving is not for the faint-hearted in Italy, and especially in Sicily. Palermo is probably the most difficult place to drive in Europe!

Outside the cities the motorways are fantastic and it’s simple to get between cities and villages. Many cities and towns now have ZTL areas that extend throughout the town or village.

*Parking lot below a Tuscan Hill town, Italy*

ZTL means ‘limited traffic zone.’ For hilltop villages and walled cities, this can mean parking at the bottom of the hill and making your way on foot.

There are escalators and shuttle buses at some of the parking lots outside tourist towns.

These are not well advertised, so go online to find the cities and towns that provide these. Montepulciano is an example of a town that has both.

One final thing to remember about moving around Italy – check-in times can be as late as 4 pm, so being able to have an early check-in or leave your luggage until check-in time should be factored into your Italy itinerary.

Step 5: Plan your accommodation

Now that you know where you’re going and how you’re getting around, you’ve made it to the final stage of our Italy trip planner. It’s time to book your accommodation.

There’s every conceivable type of accommodation in Italy including the wonderful “Agriturismo” lodgings.

*Agriturismo bed and breakfast, Sicily, Italy*

Airbnb’s are becoming very scarce in some Italian cities as they enact bans on permanent Airbnb lettings. From 2024 onwards, Airbnb numbers have plummeted in cities like Siena and Florence.

So there you have it – 5 easy steps to help you create your own trip. It doesn’t matter if it’s your first Italian trip or your twentieth, these five steps are common to everyone planning a trip.

Here are some dedicated accommodation articles to get you started on finding your perfect accommodation: