My favorite thing to do is travel in Italy – but if I can’t be visiting Italy myself, my next-favorite thing is to help other people travel better in Italy. Toward that end, I’ve put together what I’m calling the perfect 2 week Italy itinerary in this article.
This Italy itinerary is geared toward first-time visitors who want to make sure to see the highlights but may also want a few other options. But in order to make this itinerary for Italy even more broadly applicable, I’ve also listed a few possible alternates for each place in case you want to swap something out, either because you’ve already visited that city or you just have no desire to.
And before you get upset about something I’ve left out or included that makes you think I should get my head checked, be sure to read the caveats at the bottom of the page.
>> Also, be sure to take a look at my comprehensive Italy visitor guide, which is also geared toward first-time visitors but contains helpful planning information for all travelers to Italy.
Here’s my suggested two week Italy itinerary:
Quick search for flights to Venice:
There are a few details about each of these stops listed in the article below, along with some suggested alternatives if you’d like to adjust the itinerary a bit. I’ve also written a separate article about each of these stops on the itinerary, too, so if you want more detail after going through this page, then here’s where to go next:
This itinerary assumes that you’re getting an open-jaw ticket to Italy, flying into Venice & out of Rome. Although open-jaw tickets can be a little bit more expensive, they give you maximum flexibility and actually allow you to have more of your vacation time be vacation as opposed to travel time. If you can afford it, it’s absolutely worth the extra cash. (And sometimes they don’t cost any more at all, so it’s always worth checking.)
I recommend Venice as a starting point for almost any Italy trip (at least any trip that includes Venice on the itinerary!), primarily because the Venice Airport is significantly smaller than Milan’s or Rome’s airports and there’s nothing quite like arriving in Italy and your first sight being the canal city (there’s a link to information about getting from the Venice Airport into the city below).
The other major benefit, especially for first-time visitors to Italy, is that Venice runs at a bit of a slower pace than, say, Rome or Milan – so starting in Venice will give you a couple days to get your feet under you in a city without cars. And with how Italian drivers are, you’ll be pleased you don’t have to face cars right away.
Also note that for this itinerary I recommend sticking to public transportation, which in all cases but one means taking the train. You can browse train schedules and book tickets with the box to the right, which gives you access to Trenitala’s cheapest fares if you book in advance.
Quick tool to compare prices on flights to Milan (MXP) and Rome (FCO):
You’ll start your trip in one of my favorite Italian cities, Venice, with what will probably be a morning flight arrival time. It’s endlessly romantic, and also endlessly crowded.
Still, doing Venice as a day-trip from somewhere else just isn’t enough. The crowds are worst during the day because of the day-trippers, so to even give Venice a fighting chance to prove how fabulous she is you’ve got to stay at least one night.
The good news is that there aren’t too many actual “sights” in the city, so spending two nights and the better part of two days is really plenty of time to see everything you “need” to see and still enjoy a quiet(ish) Venice night.
I’ve listed my suggestions for a two-day trip to Venice on this page, which includes my top two recommendations for Venice – the stunning St. Mark’s Basilica and just getting lost in Venice.
Quick search for hotels in Venice:
>> Want to get more specific with your hotel search? Check out my article on Venice hotels to find hotels near St. Mark’s or near the train station, for romantic or unique places to stay.
Before you have a chance to be transported by the city, however, you’ve got the get there first. Here’s everything you’ll need to know about getting from the Venice Airport into Venice – by water or by wheels.
>> Here are my thoughts on what to do with two days in Venice.
As removed from mainland Italy as Venice can feel, the Santa Lucia train station is well-connected to points all over the country. You’ll leave on an early train for your next stop, the Cinque Terre, and it’ll take you about 6-7 hours to get there. And don’t be surprised if your journey includes a transfer in Milan. Here’s my more detailed article about how to get to the Cinque Terre from Venice.
>> If Venice isn’t your style, here are some alternatives:
Like Venice, the five little towns of the Cinque Terre are both beautiful and (usually) very crowded. I’ve even gone so far as to argue that the Cinque Terre should be closed to most of the people to traipse through it each year. So why am I including it on this itinerary? Because it doesn’t matter what I think about how overcrowded these villages are, you still want to see them. And I aim to please.
Quick search for hotels in Vernazza & Monterosso, two of the more popular Cinque Terre towns:
Vernazza Hotels:
Monterosso Hotels:
>> Find out more about where to stay in the Cinque Terre, with a bit of detail about each town and what kind of accommodation to expect.
You’ll spend two nights and one full day in the Cinque Terre, so pick a town to call your home base and enjoy your first afternoon and evening after you’ve arrived from Venice exploring that town (it shouldn’t take long) and scoping out your dinner options. Hike the famous trail that links the five towns the following morning before it gets too hot (assuming you’re doing this in nice weather, of course), and go for a swim in the afternoon. It’s a tough life, but someone’s gotta do it.
>> Here are my suggestions for what to do with 2 days in the Cinque Terre.
The next morning, you’ll catch a train for Florence. The trip will take you about 2.5-3 hours, and you’ll need to change trains in Pisa. If you’re not planning a longer day-trip to Pisa from Florence, this is the perfect opportunity to stash your bags in a locker at the Pisa train station and hop on a local bus to see the leaning tower and tour the nearby cathedral and baptistery. It’s a 1.5-2 hour diversion, but it’s a way to tick “Pisa’s leaning tower” off your to-do list without another hotel charge. There’s a much more detailed article on how to get to Florence from the Cinque Terre, too, if you’re looking for more information.
>> If you’d rather not deal with the Rick Steves tour groups & German tourists who can flood the Cinque Terre, some alternatives are:
As the birthplace of the Renaissance, Florence is chock-full of amazing art and architecture; I’ve talked with plenty of people who think that even with a full week in Florence you could spend the whole week running around trying to see everything and still not see all of it. There are obviously major “must-see” sights in Florence that everyone wants to see, including the Uffizi Gallery and the Accademia, so if your trip won’t be complete without seeing those then be sure to book your tickets in advance.
Quick search for hotels in Florence:
>> Want to get more specific about your hotel search in Florence? This article on Florence hotels will point you to hotels near the Duomo, near the Pitti Palace, and even some of those famous “rooms with a view.”
You’ll spend four nights in Florence, so you’ll have time to relax into the rhythm of the city a bit more (and don’t forget to eat as much Italian gelato as possible here, as Florence is well-known as one of the best places to get gelato in Italy). If you’re following the itinerary thus far without substituting any other cities, then this will be your first Italian city that isn’t car-free! Luckily, many of the most popular sights are in or near primarily pedestrian zones, so you can still get a bit of a break from automobiles. Florence is also extremely easy to navigate on foot – in fact, it’s likely you won’t need to use public transport at all.
>> Here are my suggestions for what to do with 4 days in Florence
After your 4th night in Florence, you’ll get on a morning train for Rome – it’s a journey of about 2.5-3 hours, and it’s a direct trip. Read everything you’ll need to know about getting from Florence to Rome.
>> If you’d rather sidestep Florence, here are some alternatives nearby:
Day Trip to Siena from Florence
If you get itchy feet with four nights and more than three full days in the same city, then a day-trip from Florence is a great idea – and Siena is the most obvious choice. It’s one of those cities that people fall in love with instantly, and with good reason. Siena is a popular day trip from many places, and (like Venice) is even better when the day-trippers leave in the evening – but if you can’t spend a night inside the old city walls, then spending a day exploring the medieval center is well worth it.
>> Read more about how to get from Florence to Siena
Want to stay longer? Quick search for hotels in Siena:
>> Some possible substitutions for Siena as good day trips from Florence are:
Rome isn’t called The Eternal City for nothing – and you really could spend an eternity there without seeing everything there is to see. I find Rome exhausting and a little overwhelming (it was especially so on my first visit), which is why I’m allotting so much time for the city on this itinerary. If I don’t have to rush around in Rome it means I can allow myself a bit of down time when I need it.
Quick search for hotels in Rome:
I don’t think it much matters what order you do things in Rome, but you’ll want to give yourself the better part of a day to see Vatican City, and you can also easily combine many sights of ancient Rome (including the Colosseum, Roman Forum, Palatine Hill, and Pantheon) into one day.
>> Here are my suggestions for what to do with 5 days in Rome
Rome is big, so be sure to acquaint yourself with Rome’s transportation system so that you won’t exhaust yourself too much.
>> If you’re looking for an alternative to Rome, there isn’t one. But if you really don’t want to spend five days in Rome, you could potentially split that time between these cities:
Day Trip to Pompeii from Rome
With four full days in Rome (one of which is basically taken up by a Vatican City tour), you may not feel the need for a day trip outside Rome. On the other hand, the city may just get to be too much for you after a few days!
Pompeii is actually more easily visited from cities like Naples or even Sorrento, but you can do a day trip to Pompeii from Rome. Melanie at Italofile has written up a great post about how to do Pompeii as a day trip from Rome – she lists both a few of the guided tours available as well as the options and cost of making the trip on your own, so you can decide whether it’s worth it and, if it is, which you prefer.
Want to stay closer to Pompeii? Quick search for hotels in Naples:
>> Other alternatives for a day trip from Rome are:
You’ll fly out from Rome on your final day in Italy; if you’ve got a flight that isn’t leaving at the crack of dawn, then you’ll even have a few extra hours on the morning after your 5th night in the city to explore any last-minute spots you want to see before you leave. And just remember, whatever you didn’t see on this trip is probably going to be there for awhile – so enjoy this two week trip to Italy, and start planning your return on the flight home.
Caveats (AKA Don’t Send Me a Complaint About This Itinerary Without Reading These First)
I know I’m going to hear from some people who are horrified that I’ve left something out, or included something that they never would. So here are my caveats which will, I hope, cover all bases in terms of the questions I’ll inevitably get about this post. I suppose we’ll see if this works…
photo at top by Hvnly