Italy Bucket List Itinerary: The Perfect Two Weeks

NOTE TO READERS WHO ARE INDEPENDENT TRAVELERS: If you’d like to simply be pointed in the right direction but craft your own Italy bucket list itinerary, then I recommend looking at my article about how to create the perfect Italy bucket list itinerary – it’s precisely what I do when I’m making my own itineraries, and how I go about answering your bucket list itinerary questions.

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 bucket list itinerary in this article.

Table of Contents

This Italy bucket list itinerary is geared toward first-time visitors who want to make sure to see the highlights and check some big items off their bucket list, 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 alternatives 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 (that in your opinion should be on everyone’s bucket list) or included that makes you think I should get my head checked, be sure to read the caveats at the bottom of the page.

Here’s my suggested two week Italy itinerary:

  • Venice – 2 days
  • Cinque Terre – 2 days
  • Florence – 4 days (with a day-trip to Siena)
  • Rome – 5 days (with a day-trip to Pompeii)

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 bucket list 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.

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 Terracotta Army is a sight I won’t forget in a hurry. this has always been on my bucket list itinerary I recommend sticking to public transportation, which in all cases but one means taking the train. 

Flights to Venice aren’t always as cheap as flights to Milan or airfare to Rome, however, so shop around. You may not be able to find a flight directly into Venice, in which case the order of this itinerary may need to be adjusted.

2 Days in Venice

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.

My top two bucket list recommendations for Venice – the stunning St. Mark’s Basilica and just getting lost in Venice.

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.

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.

Venice Alternatives

If Venice isn’t your style, here are some alternatives:

  • A Lake Town – Many of the towns along Lago Maggiore or Lago di Como are delightful and ready-made for tourists. They aren’t going to be crowd-free, but they’re almost unbelievably beautiful and picturesque, and will provide you with another way to get a slow start to your Italian trip.
  • Verona – Just about an hour outside Venice, this beautiful city is famous for being the setting of the “Romeo and Juliet” story and for its stunning Roman amphitheatre. Opera lovers will want to visit during the summer season when you can see an opera sitting on Roman-era marble seats.
  • Milan – Okay, this city definitely is not a slow start to an Italian trip, and for most tourists it’s actually not even worth the time. But if you’re into opera, shopping, or “The Last Supper” then it’s the place to be. And since it’s sometimes cheaper to find cheap flights to Milan than to Venice, it’s a default starting point for many trips.

2 Days in the Cinque Terre

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.

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.

Cinque Terre Alternatives

If you’d rather not deal with the Rick Steves tour groups & German tourists who can flood the Cinque Terre, some alternatives are:

  • A Lake Town – Assuming you didn’t opt for this alternative in place of Venice earlier, you can enjoy a couple days in a town on Lago Maggiore or Lago di Como at this point instead. Of course, in the summer these lakes are also invaded from the North by German tourists, but I never said they weren’t crowded.
  • Bologna – This under-rated city is the heart of Italy’s primary food region, so it’s a must-stop on any foodie’s tour. It’s also well off the tourist track, although it’s home to the oldest university in Europe; so while you won’t find vendor carts selling crap in the piazze, you will find the areas around the university overflowing with students.
  • Portofino – Slightly North of the Cinque Terre, this Ligurian town is part of the Italian Riviera, and it lives up to that title. It’s gorgeous, yes, and it’s also notoriously expensive. It’s frequently a stop on Mediterranean cruises, so it’s very tourist-friendly in that sense, and it’s a good place to get your glamour on.

4 Days in Florence


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.

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.

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.

Florence Alternatives

If you’d rather sidestep Florence, here are some alternatives nearby:

  • Siena – Assuming you’re not opting for a day-trip to Siena, it’s a city that positively oozes charm and is even better after the day-trippers leave. So if you can spend a few nights in the old city center (inside the old walls), that’s a very good thing, indeed.
  • San Gimignano – San Gimignano is one of many beautiful hill towns in Tuscany; it’s another popular day-trip from Florence or Siena, although it lacks a train station so it requires either a bus trip or a rental car. If you’ve got a rental car, it’s an excellent base for exploring Tuscany.
  • Perugia – Want to avoid Tuscany altogether? Head for the capital of the neighboring region of Umbria, Perugia. It may be a good-sized city, but it’s not nearly as touristy as Florence, and you can use it as a home base from which to explore the hill towns of Umbria.

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.

Some possible substitutions for Siena as good day trips from Florence are:

  • Pisa – If you didn’t spend a couple hours in Pisa en route to Florence, it’s a good day-trip. Just about 1.5 hours away, the city is much more than just the tilted tower. With a full day, you could explore far beyond the tourist hordes.
  • Cortona – “Under the Tuscan Sun” fans will probably want to visit this Tuscan hill town, made famous most recently by Frances Mayes. It’s beautiful, and only 1.5 hours from Florence by train (to Cortona’s main Camucia station).
  • San Gimignano – This lovely hill town is another popular day trip from Florence, and is also better if you can afford to spend more than just a day there. Still, it’s extremely charming and historic. San Gimignano doesn’t have a train station, but you can catch a bus from Florence.

5 Days in Rome

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.

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.

Rome is big, so be sure to acquaint yourself with Rome’s transportation system so that you won’t exhaust yourself too much.

Rome Alternative

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:

  • Naples – Naples is the birthplace of pizza, so it’s a good stop on a foodie tour of Italy. It’s also a great base from which to explore both Pompeii and Herculaneum, the towns destroyed by Mt. Vesuvius.
  • Positano – This famous town along the Amalfi Coast is extremely gorgeous and extremely steep; it can be expensive depending on the season, but the sun-soaked beauty of Positano is tough to beat.
  • Sorrento – And in case Positano is a bit too well-traveled or expensive for you, another town you might want to check out is Sorrento. It’s still quite crowded in the summer, but because it’s not technically part of the Amalfi Coast it can be a bit less expensive.

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.

Rome Day Trip Alternatives

Other alternatives for a day trip from Rome are:

  • Naples – As mentioned, Naples is where pizza was born. If that’s not reason enough to go, then there’s also the fact that most of the actual stuff they’ve discovered at Pompeii isn’t at Pompeii. It’s in a museum in Naples. Naples is about a 2-hour train ride from Rome.
  • Sorrento – A day trip to Sorrento, just north of the Amalfi Coast, is a great way to explore this gorgeous area without paying the often high prices for hotel rooms in these coastal towns. After taking the train to Naples from Rome, you can hop on a boat for Sorrento – it’ll take less than an hour, and it’s a lovely way to enter Sorrento.
  • Assisi – You don’t have to look South of Rome to find day trips, as evidenced by the Umbrian town of Assisi. It’s about a 3-hour bus ride from Rome, and it’s an incredible town, whether you’re a pilgrim or not. The Basilica is a UNESCO World Heritage Site.

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 check off your Terracotta Army is a sight I won’t forget in a hurry. this has always been on my bucket list 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.


(AKA Don’t Send Me a Complaint About This Bucket List Itinerary Without Reading These First)

I know I’m going to hear from some people who are horrified that I’ve left a bucket list 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…

  • What’s perfect for you isn’t perfect for me. You’re absolutely right. I’ll be the first to admit that I think it’s kind of impossible for one traveler to tell another traveler what the “perfect”bucket list itinerary is. You can get close, but each person’s travel style and personal preferences are going to make it impossible for one bucket list itinerary to really be ideally suited to a large number of people. But there’s a reason the “tourist trail” is well-traveled. It’s because many travelers do the same things and visit the same places, so even if this Italy bucket list itinerary isn’t perfect for you, you can probably make it perfect with a small tweak or two.
  • Two weeks is not enough time to see Italy. I agree with this statement 100%, and I also know that the vast majority of American travelers are lucky to get 2 weeks off in a year. If you’re one of the lucky ones, or if you’re from a more generous country when it comes to holiday time, then use this bucket list itinerary as a starting point and build on it for the rest of your trip. And for those of you who only have two weeks, just remember that Italy will be waiting for you whenever you come back.
  • You can’t possibly say you’ve seen Italy without seeing (fill in the blank). Umm, yes you can. When you spend time exploring a country, you’re seeing that country – or at least some aspect of it. You can’t say you’ve seen all of Italy if you haven’t actually done that, but to say that visiting Italy “doesn’t count” if you don’t hit someone’s idea of a bucket list of sights or cities is absurd. The only exception to this rule is that you can’t say you’ve seen Italy if you’ve never been outside an Italian airport.
  • You shouldn’t go to (fill in the blank), it’s just a tourist trap. In general, I’m not a fan of tourist trappy sights, but if someone absolutely must go to Pisa simply to get a photo of themselves propping up the leaning tower cause it is on their bucket list, who am I to say they shouldn’t do that? Likewise, if I say that I love Venice and can always find a quiet corner even in the busiest season, no one’s going to be able to convince me I shouldn’t still love Venice just because it’s often overrun with tourists.
Italy Itinerary: The Perfect Two Weeks map

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