The Ultimate Italy Itinerary

As one of the most iconic and romantic countries in Europe, if not the world, Italy is naturally the focus of many a jet-setter’s itinerary. From famous landmarks to delicious cuisine, to near-unbeatable island and beach breaks, if the weather doesn’t impress you, the wine and the culture will.

It’s why we've put together a complete guide to building an Italy itinerary, based around some of our absolute favorite cities and attractions across the nation. Much like our other itinerary guides, we make suggestions on where you might want to travel in Italy so that you can build your own timetable and vacation strategies. Alternatively, you can use our examples for seven, 10, and 14 days and stick to them as closely as you’d like!

Whether it’s your first time visiting Italy or your fourtieth, let’s take a closer look at what you should include in the perfect itinerary here, and some tips on how to make the most of your Mediterranean breakaway.

Italy itinerary overview

Anyone who’s been to Italy before - like plenty of us here at SIMOVO, actually - will tell you that’s possible to explore just one or two of Italy’s most famous cities across a week or two and still have things left to see and do. However, the best Italy itineraries take in as much as possible from the country’s “greatest hits”, meaning you may well find yourself sticking around in, say, Venice, for a little longer than your plans initially accounted for.

Regardless, when it comes to hitting all the best spots we explore in this guide, we recommend taking trains across the country - it’s fun to go on a road trip, sure, but driving isn’t always the most convenient way to go around Italy. At least when you’re on a train, you can still take in the fantastic natural scenery and much of the historic cityscapes Italy has to offer.

For example, a basic train journey from Rome to Florence will usually only take around an hour and a half, maximum. Going via Rome to Milan, however, will usually take around three to four hours - so, we’ve set up our itinerary suggestions below to try and help you make the most efficient routes between each of our favorite places. Check out the Eurail Italy Pass and you’ll save money, too.

On a different note, we recommend you find and download the right eSIM for Italy before you travel. There are plenty of WiFi hotspots across the country, but not only are there zero guarantees they will be 100% safe, they’re not always free to use. Plus, at least when you have an eSIM, you can be sure SIMOVO will connect you to the best available mobile network depending on where you are.

The itinerary items and suggestions we’ve made below can all be enjoyed on a range of budgets. However, it really does pay to compare flights and ferries across the year, and to consider your accommodation needs when it comes to staying in the big cities (or in their vicinity). We recommend taking a look at our Italy trip cost guide for a complete lowdown on what you can expect, financially.

It’s also worth noting that the advice we give in this guide relaytes largely to the biggest attractions across the country, not necessarily the island breaks that you can still enjoy regardless of where you stay. Check out our Amalfi itinerary guide, for example, if you intend to stay in the south of Italy and specifically want ideas for a trip solely to that area.

Best places to visit in Italy

The SIMOVO crew agrees that there are five must-see regions of Italy that deserve to be explored regardless of how long you intend to travel for. Making cities like Rome, Venice, or Milan your home bases for your trip are a must, but you should also add in Florence and Naples to ensure you get to enjoy a scenic route or two along the way.

Rome

Rome is Italy’s beating heart, and it’s in the capital where you’ll get to feast your eyes on some of the nation’s most incredible historic architecture. It is, of course, the former seat of the Roman Empire, but beyond that, you’ll want to take in the incredible food, breathe in the Meditteranean air, and just enjoy people-watching from a cafe or two. It’s a bustling, historic metropolis that should be at the heart of your Italy itinerary.

Florence

Florence, too, is a city that’s rife with history, and it’s particularly popular with art lovers, as it’s considered the birthplace of the Renaissance movement. While Florence itself is a fairly small area, it gives way to the absolutely gorgeous, rolling countryside around Tuscany, meaning we seriously recommend you take a drive or two out of the area for some scenic sights if you’re hiring a car.

Venice

Chances are, if you’ve heard of Venice, you’re already thinking of canals and gondolas, and that’s absolutely where you should start if you build a trip here into your itinerary. The streets here are intricate and stylish, giving more power to the idea that it’s one of the most romantic regions in Europe. While it can get very popular with tourists, if you travel during a shoulder season, you’ll have a great time.

Milan

Milan is world-famous for being Italy’s seat of luxury and opulence, whether it’s fashion, cars, or dining. It doesn’t tend to feature too highly on general itineraries - you probably have to love fashion to make the most of it here - but it’s nice and close to the stunning Lake Como, so use it as a stopping point.

Naples

A one of Italy’s oldest cities, Naples has just as many fascinating sights to offer as Rome does. It’s also much less crowded due to lower tourism, but it’s an authentic Italian experience all the same! And, it’s also a great vantage point if you’re exploring the Amalfi Coast (as mentioned earlier).

Italy itineraries based on length of trip

Below, we’ve put together some brief schedules you might want to consider if you’re exploring wider Italy and want to pack in as much as you can. Feel free to adjust them as you see fit, but remember, we’ve arranged them with ease of travel in mind.

Italy itinerary for 7 days

• Days 1-2: Travel to and make your home base in Rome, and enjoy the city
• Day 3: Head out to Naples for the day, either stopping or heading back to Rome
• Days 4-5: Ideally from Rome, travel to gorgeous Florence (and again, consider rebooking where you stay
• Days 6-7: Finish your stay in delightful Venice up on the north-east coast

Italy itinerary for 10 days

• Days 1-2: Start in Florence and/or the Amalfi Coast
• Days 3-5: Head to Rome and make it your base for a few days
• Days 6-7: Go explore Florence and the Tuscan countryside
• Day 8: Take a trip to Milan, stopping overnight or heading back
• Days 9-10: Finish your trip with a gondola ride in romantic Venice

Italy itinerary for 14 days

• Days 1-3: Start up in Venice and enjoy the north-eastern air
• Days 4-5: Check out Milan on your way through and explore Lake Como
• Days 5-8: Take in the sights of Florence and the Tuscan countryside
• Days 9-12: Spend a few days in Rome and take in the history
• Days 13-14: Finish your adventure in Naples and overlooking the sea

Best time to visit Italy

As you can imagine, any time between the spring and summer here will be very popular with tourists - and the summers get extremely hot at their height. That said, for a cooler, less chaotic trip across Italy, you might want to book flights and accommodation in late winter or early spring. That said, do be aware that some activities may not be available (and you’ll still need to pack some warm clothes for the breeze!).

Now you have more than a good idea of how to explore Italy to its fullest, be sure to grab an eSIM for Europe so you’re always covered for mobile data. Ciao for now!