Italy 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 itinerary, then I recommend looking at my article about how to create the perfect Italy itinerary – it’s precisely what I do when I’m making my own itineraries, and how I go about answering your itinerary questions.

planningMy 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:

  • 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)

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.

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.

Quick tool to compare prices on flights to Milan (MXP) and Rome (FCO):

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.

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:

  • 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.

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:

  • 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.

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:

  • 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.

>> 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:

  • 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.

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:

  • 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. 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:

  • 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 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.

Read more about how to get from Rome to Fiumicino Airport

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…

  • 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” itinerary is. You can get close, but each person’s travel style and personal preferences are going to make it impossible for one 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 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 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 checklist 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, 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.


photo at top by Hvnly

246 thoughts on “Italy Itinerary: The Perfect Two Weeks

  • jayalipi

    Hey Jessica!!

    thanks a ton for your wonderful article! i’m from India and it was a dream to visit Italy! i never wanted to plan a trip with a travel agent and just run around! your article has really given me the courage to plan an independent trip. i’m plannig the trip during November, that too in later half. everyone is discouraging a trip to Italy in November though, but don’t have an option. could you please tell me should I drop the idea of cinque terre at that season? but reading your article I really loved the place. but if you really think that it wont be that great an idea then could you please suggest any other place for those 2 days?

    thank you so much πŸ™‚


    • Jessica Post author

      Here’s a bit of information about traveling to Italy in November:

      It depends a bit on what you want to do in the Cinque Terre – but yes, generally speaking, it’s not as pleasant at that time of year. It will likely be quite stormy and rainy, making the hikes between the towns not very fun. In some cases, the trails are even closed in the off-season for repairs.

      There are a few alternates listed above under the Cinque Terre section, but you might look in particular at cities like Bologna or Parma (great for food) or spend a couple of days in a town like Siena instead of making that a day trip from Florence. You could also spend those two days in Orvieto, Perugia, or any number of beautiful hill towns in central Italy.

  • Muna

    Is it okaay to have this for a summer trip I mean for July…I know its very hot there…but what r ur thoughts?

  • Nancy

    Is it ok to use this itinerary for a trip to Italy in February? Are there some places that will be closed due to off season/winter? Also please can you advise on the weather in italy in February. This will be my first trip!
    Thanks for your help!

    • Jessica Post author

      Here’s my February page, including weather averages & information about the potential for shorter open hours at attractions:

      In general, this trip is good for nicer weather – but it only takes a small tweak to make it good for colder/wetter weather. I wouldn’t go to the Cinque Terre during February, since the main attraction there is the hike between the towns. The trail can be closed off in the winter for repairs, and the weather could make it really unpleasant anyway. Look at some of the other options listed above for a few days instead of the Cinque Terre – a place that’s focused on museums, culture, food, and other indoor activities will be much more enjoyable than the coast at that time.

  • Dan

    Is there a tool for looking up “open jaw” airfares on this site?
    Or even something for looking up one-way fares?

    • Jessica Post author

      In most cases, airfare booking sites have an option to look for one-way trips only – and in some cases, there’s an option for multiple legs. With the airfare search tool at the top of this page, you’ll get to the one-way option after you click the “Search” button and get to the next step.

  • dana sharma

    we are traveling to Italy last two weeks of May.We are flying into Rome and the areas we would like to visit and spend a few days at each are the Almafi Coast, Tuscany(3-4 days here), Rome and Florence also we are total foodies and LOVE wine so can you help me out with an itinerary as I am independent traveler and don’t want to pay a travel agent.

  • ArtBaron

    Can someone give an indication of what the whole 2 weeks would cost for a couple? Exclude airfares etc. I just am interested in how much I should budget for mid range hotel food and local transport and entry to a reasonable selection of sites.
    I am hoping to travel in June 2012.

  • Vafirish


    I actually follow your itinerary right now and am having a blast. Just reach Rome and I thought of writing this comment as a thank you note for writing such detailed itinerary which is easy to understand and follow.

    Keep up the good work.

    Best regards,

  • Amber

    My husband and I are traveling to Italy for our first time Sept 24th – Oct 9th. We are almost following your intinerary except backwards (Rome 5 nights, CT 2 nights, Florence 5 nights, Venice 2 nights). My question is in regards to staying in Florence vs staying in the Tuscan countryside. We love wine and food and not huge museum fans. I wonder if we will not get the same experience staying in Florence as we would in the countryside. We have a a ton of points with Westin so we were planning on Florence so we can use our points. Just curious your thoughts on that. Also if we stay in Florence should we rent a car for one day and drive ourselves around Tuscany? If so any recommendations on must see places? Thanks!

    • Jessica Post author

      Even if you’re not huge museum fans, it’s likely you might want to visit the Uffizi and Accademia – Florence’s two big museums, with some of the most famous art in the world – but if you plan ahead and buy tickets online you can do both of those in one day. And with five days total, it might be more interesting to stay in a different town in Tuscany and do Florence as a day trip. If you do that, you could rent a car for whatever time you’re in Tuscany – 4-5 days – and then (assuming you get one with GPS, which I recommend) you can drive around through wine country for a few days exploring the smaller towns. I’d still recommend taking the train or bus into Florence for a day trip, however, because it’s a pain in the neck to park there.

  • Esther Chit

    I am planning to visit Italy from 16Sept to 23Sept, plan to go Milan, Venice, Florence & Pisa and Rome & Vatican. Is that too rush? Do you think it is good idea?

  • Brenda

    We are planning to be in Cinque de Terre as part of our Italian vacation and then to Venice, Florence and Rome. My husband just decided he wants to bungee off the Ponte Colossus. We can’t decide between renting a car for the whole 9 days or taking trains. I haven’t been able to figure out if the only way to Veglio-Mosso where the bungeeing is can be reached via train, or if we would have to rent a car for that leg. I’m also wondering how many hours out of the way it is going to be for him to jump off this particular bridge.

    • Jessica Post author

      Wow, Brenda – I hadn’t even heard of this bungee place until I looked it up just now!

      So, unless your itinerary was already going to be including either Milan or Turin, then yes – getting to the bungee spot is a detour. I’ve found train service as far as Biella, but that’s not close to the Ponte Colossus. Renting a car is your best bet for getting to the bungee jump itself – although given the rest of your itinerary (all in big cities well-served by trains) you may find the car to be more of a hassle if you keep it longer than that one day.

      I’d recommend checking approximate drive times on the Via Michelin site ( for whatever routes you’re planning – I’m not sure where you’ll be coming from or heading to before/after the bungee stop.

  • Khurram

    I’m traveling with my wife to Italy for first time, from Sep 1 to 8, 2011. We have an open jaw ticket, arriving in Rome & leaving from Venice. I like your 2-wk itinerary. However, we only have 1 wk. We’re not into museums, arts, etc. You think we should just skip Florence altogether? What itinerary would you suggest in this case? How can we incorporate day trips to Pompei & Pisa into this itinerary?

    • Jessica Post author

      If it were my trip (which it’s not), I would pick three stops at the very most – and more likely two – with only a week. I really try to avoid moving around too much during short trips, because that just means I’m spending too much of my precious vacation time in transit. With one week, you could spend 3 days in Rome and 2 days each in Venice and one other city, or 4 days in Rome and 3 days in Venice (the latter itinerary would give you more flexibility for day trips). If you really don’t want to do museums/art, you’ll have a much shorter to-do list in each of those cities. πŸ™‚

      Here are some tips to help you plan the perfect Italy itinerary no matter where you want to go:

  • Rick

    Hi Jessica,

    Our trip will mirror your 2-week schedule…

    Just wondering if you have any major do’s or don’ts or must see’s and/or things that can be crossed off the list that seem to be popular in top 10 lists of things to do…


    We will be going to Venice for a day & 1/2 – St. marks is booked – Go to islands?

    CInque Terre for a day & 1/2 – nothing booked, just hike…resturant with a view you liked?

    Florence for 4-days with a day trip to Siena and stop in Pisa on the way down – You say bus, a friend says rent a car…??? Uffizi and academia booked.

    Rome for 4 & 1/2 days with a day trip to Pompaii – Colosseum dungons/upper tier, forum and panatine hill booked, will book vatican things very soon.

    If you have comments on any of the cities on do’s or don’ts, that would be great but don’t worry about it if you don’t have time…We will climb some domes and Pisa tower.

    We have a lot of it mapped out but there might be a thing or two you did or didn’t do that might help us.

    • Jessica Post author

      If you want my “top 10” lists, click on each city/area listed on the right-hand menu near the top of the page – so, for instance, click on “Florence” and then on the right-hand side of THAT page there’s a link to my “top 10 things to do in Florence” article. Same goes for Venice and Rome (I don’t have a top 10 list for the Cinque Terre, although there’s an overall guide to the area).

      Those lists will answer some of your questions here – yes, I think the islands are an excellent thing to do in Venice, hiking is really the thing to do in the Cinque Terre. For your other questions:

      * Each town has restaurants with great views or just great outdoor vibes – even if you’re not perched over the sea, it’s lovely to sit out in a piazza and listen to the waves as you have dinner.

      * If you’re sticking the itinerary I outlined, there’s no reason to rent a car just to do the Florence-Siena drive. Parking in both places is a pain, and traffic can get annoying. If you’re taking a day to wander aimlessly through Tuscany, however, with a brief stop in Siena as part of that, then by all means rent a car for a day.

  • kuntal

    Hi Jessica,
    I cannot begin to thank you how much this website is helping me to plan my vacation. You have mentioned all the places I wish to see, however, I am making few changes. I will be following the itinerary in reverse order i.e. start from Rome and end in Milan. I will be skipping Venice altogether as I have already been there. Also, from Rome I want to spend some time on the Amalfi coast/Capri (2-3 days) before I head to Florence. Do you have any detailed write -up on the same? This is what I think: Train from Rome-Naples and ferry to Capri. Spend 1 night in capri. next day head out to Amalfi, stay in Amalfi and explore Ravello, Positano. From Amalfi go to Naples and see pompeii on the way if possible and then train to Florence. What do you think?

    Thanks a ton in advance!

  • Jay

    Hi , Jessica! First off, thanks for putting this site together. It’s extremely helpful and I have yet to explore the site in its entirety, so I can just imagine how much more helpful this site will be once I have a chance to sit down and navigate it thoroughly. I do have a fairly simple, yet very general, question that you may or may not be able to answer and perhaps you may have the answer somewhere on here. In any case, we’re looking to travel to Italy for our honeymoon next October and I’m trying to work on our honeymoon budget. Is there anyway you can give me a ballpark figure regarding the expenses we’ll incur traveling to Italy? Or rather, minus the flights, how much is needed to enjoy our travels? I know this is a very difficult questions to answer given that we all have different tastes, I just have no idea how to prepare a budget for this, so I’m curious as to what you spend when you go for a two week getaway. Any help whatsoever would be greatly appreciated.



  • Maria

    Hello Jessica!
    My name is Maria and this year I have read pretty much all your articles! πŸ™‚ My fiance and I have been planning our two weeks in Italy for 6 months. Your website is the the best place to learn everything someone needs to know about Italy. We have learned useful information about staying, eating, walking, even tipping in Italy!!! πŸ™‚ Really, I think I’m ready for my pop-quiz now! I even know most type of pasta because of you πŸ™‚
    After memorizing most of your articles and printing out your transportation info, we did go to Italy and we had the most amazing time. I think it is officially my favourite country in the whole world πŸ™‚ Since the moment we got on our plane home I have been trying to figure out when we can go back again.
    So I guess what I am trying to say is a big THAAAANKS for all the information and the tips you provided!! You are amazing, I have never found a better travelling website!
    Keep up the good work!

    Next summer we are planning to go to America for our honeymoon [yeiiii!! πŸ™‚ ] We are thinking about 5 days in Los Angeles, 3 in Honolulu, 3 in Maui, 4 in Las Vegas and 5 in New York. What do you think? Have you got any suggestions for us?

  • Julie

    Hi Jessica
    Your site is great reading with lots of very helpful information. My husband and I are in our 60s and travelling to Italy for the second time (first time was in 2009 on a u-beaut tour where we spent a day or part thereof in Venice, Florence and Rome). We loved it and want to re-visit to experience it in more detail. We are planning to travel next May and will have about 2 weeks in Italy before travelling to France for one week in Paris and a week in the Dordogne. I have noted your itinerary and just wanted to run our tentative plan by you. We fly into Rome and plan to spend three nights there, travel by train to Cinque De Terre and Florence spending 2 & 3 days respectively in each place with side trip to Sienna. We are considering if it is feasible to travel to Amalfi coast from Rome for 1 or 2 days before going north. We would also like to re-visit Venice but wonder if this will be too much out of the way when we are planning to travel (probably driving taking two days so we can stop on the way) to Paris. Would you mind giving your advice please. Kind regards Julie

    • Jessica Post author

      I have Rome, Florence, Siena, Cinque Terre, & Venice on my 2-week itinerary above, so I definitely don’t think it’s too much to include Venice in a 2-week trip like that – unless, of course, you’d rather do the Amalfi Coast instead. If you prefer to visit the Amalfi, I’d suggest that you take a look at this 3-week itinerary article:

      It’s not the correct timeframe for you, obviously, but it will give you an idea of the transportation time to the Amalfi Coast from Rome. It’s a long travel day, so you need to make sure you know how long it takes before you commit to it – especially because it may impact how long you want to stay once you get there!

  • Barbara

    Have you done any other itenaries for other countries (Portugal, France, etc.)?
    Thank you.


  • Walter

    I went to Puglia in October and it was wonderful! Although the season ends in September we still enjoyed warm weather. But yes, some hotels and restaurants were closed already and the sea was pretty chilly. The advantage: You don’t get too many tourists and the prices are seasonably low.

    If you have freedom to plan I suggest a two week roundtrip either in spring or autumn. Summer is hot and very busy. Puglia offers great landscapes, picturesque cities and splendid masserie (former country houses turned into luxury hotels).

    Please check out our travelogue and travel itinerary on

  • Leslie

    VERY helpful article! This is almost our exact Italy itinerary so this helped us get the nitty gritty details down. What train/website did you use to price out the above train rides? Thank you!

  • Martha

    Hi Jessica,

    I’m a 56 yo woman who will be traveling by myself and taking my first big trip by myself. Just when I think I’ve decided I need an escorted tour, along comes your website. I hope to be going in May. What do you think about going by myself vs. going with a group? Btw, really good info on Rome, Florence, and Venice, which will help me plan my free time if I decide to go with a group. Thanks!

    • Jessica Post author

      I’m biased, Martha, but I do think traveling independently (i.e. planning your own trip rather than going with a tour) can be more rewarding. It does require more planning work, of course but I think that’s part of the fun. πŸ™‚ It all depends on your own comfort level, with traveling solo, doing all the planning, etc. – if you’ll get to Italy either way, that’s a good thing!

  • kaylee

    Hello Jessica i want to take a 1 month trip to italy in september and its going to be in florence. Do you think you could make me an itenery pleaze i would really apreciate it! BTW its with three of my friends ( ;


  • kaylee

    well anyway thnx lots!!! But i have another question i was wondering would you reccomend anything to do and what to eat pleze pleze i need to know im terrible at planning anything will do thnx sooooooo much!!!!!

    • Jessica Post author

      This whole website is a treasure trove of what to do & see & eat, Kaylee. On the right side of the page, you’ll see a menu called “Explore Italy” – click on the names of the places you’re going, and you’ll find details about what to do in each place. Under that same menu, there’s also an article on “Italian Food,” with more links to suggestions about what to eat & how to find good food. There’s lots of information here for you to help you plan!

  • MAL

    Definitely using this helpful itinerary as a guide, will be doing most of the things listed but plan on skipping Cinque Terre. Very interested in “seeing an Italian soccer game,” any suggestions in where we might be able to squeeze a soccer game in this Italian itinerary (late May in particular)? Thanks in advance!

  • Lisa Matchulat

    I stumbled upon your website and it was fairly close to the exact itinerary my fiance would like to plan for our honeymoon this September. We are going for a bit more relaxed pace, so we were planning on cutting out the Rome portion and spending extra days in Cinque Terre. The best open jaw flight prices we’ve found have been starting in Florence and departing from Venice. So we were thinking we’d do your itinerary in reverse (Florence/Chianti, Cinque Terre, then Venice). Any tips for modifying the itinerary to make it work in reverse?? Mostly we’re trying to figure out our transportation between each destination. Any advice would help as this is our first trip to Europe. Thanks!

    • Jessica Post author

      There isn’t really anything that makes reversing the itinerary different – the travel times between cities is still the same, as are ticket prices on the trains. The thing you’ll need to look up (which you’d need to confirm anyway) is the departure times for each train. You can look up each train trip using the Rail Ticket Search tool at the top of this page to see your trip options:

  • Loren

    I love the articles you have on here. I will be traveling in mid May with my college on a Culinary tour, but also doing site seeing.
    There will be some of us that would like to see Italy(Rome andReggio Emmilia mainly)from the eyes of college students at night. Do you have any recommendations for what we should and shouldn’t do, or where to go?

  • Crystal

    Hi Jessica, thank you for all of your great info, it is seriously amazing! My fiancΓ© and I are going to France and Italy this September for our honeymoon, so needless to say this website is bookmarked πŸ™‚ We plan to start in Paris and then catch up to your itinerary starting in Cinque Terre. Can you recommend a good travel option for us to make it from Paris to to Cinque Terre? We originally thought to take a flight early in the morning to Pisa, but we would have to take an early morning train (5 AM) to Orly to catch the 7 AM flight to Pisa. Then we thought it might be more time and cost effective if we just took an overnight train from Paris to Cinque Terre, and avoid waking up early in Paris and paying for flights and an extra night in a hotel. BUT! We are having difficulty figuring out a way to actually do that, as it seems there aren’t any easy ways to take a late night train out of Paris and end up in Cinque Terre by the morning. Can you pleaseeee help?

    • Jessica Post author

      The airports that I’d check would be Pisa and Genoa (Genova). From either of those cities, you’d then take a train to the Cinque Terre. I don’t think a bus is feasible – the Cinque Terre aren’t on a main international bus route.

  • Tracy

    Hi Jessica, Im planning a solo vacation to Italy in September and want to see Florence, Venice and maybe squeeze rome into it (i hope i can). I will be coming in from France and i’m trying to draw up a perfect itinery.

    1. How do i plan the trip from france Flight or Train? what city in italy first?

    2. What to see in each city and how many days? Hot tourist spots please

    3. Ideas on nice hotels? Very decent but not too expensive

    4. Can i do day trips in between? How do i move around?

    5. Is 8 days a stretch for the perfect 2 weeks itinery?

    I like history and culture, romance, shopping, spa, theme parks, restaurants, beach.

  • Charlotte

    I am planning a two week trip with my family to Italy in December what do you recommend?

  • Ranjini

    Hi Jessica,
    I just got back from an amazing 2 week vacation in Italy and wanted to thank you for this wonderful article which was really a treasure trove of information for me. I am from India and was always keen on visiting Italy. I came across your article and it really helped me in putting together a perfect 2 week itinerary . We were a group of 4 people and there was something for everyone in the itinerary. We made sure we covered your top 10 things to do list in each city .I got so much information , the nitty grittys from the article, that we could spend more time sight seeing and soaking up the place rather than figuring out the logistics all the time! I personally fell in love with Florence and would love to return there some day. Thanks again for helping me put together my dream vacation:-)


  • heidi

    Hey Jessica,
    I have loved reading your site! lots of great information!
    we will be traveling to france and italy next week and are thinking about getting an 8 day train pass ($413 pp) but when i look at all the trips individually it adds up to actually cost a bit more as in italy with the pass they still charge you an extra $30-$60 on top for each trip.
    What do you think about the pass? is it worth it?
    ciao Heidi

  • jay c

    hi jessica,

    your article is excellent and i am basing my 2 week family trip to italy on your itinerary. my only thing is that when we sat down and listed our “must see” places, it included all the spots on your itinerary plus the amalfi coast (we were thinking staying in positano and taking a day trip to capri). if you had to do it, how would you incorporate positano into a two week itinerary? how would you split the days? also, assuming that we are going north to south on our open jaw, i was thinking of going from florence to positano and then backtracking to rome so that we end up in the city we are flying out of. what are your thoughts?

    thank you!

  • Alicia

    Hi Jessica,

    I enjoyed all of the information you provided on this page and I just have a few questions. My husband and I are beginning to plan our first trip together to Italy (2 weeks) and we are considering using this Itinerary you suggested. After doing some research I really feel it is a nice variety for the amount of time we have to spend there. We are thinking about leaving early May, so I already visited Expedia to see what flights looked like. Your suggestion of flying open jaws is also very sensible, but the prices to do so are astronomical. Just to fly into Venice was $1845 pp. So, I then did a round trip flight into and leaving from Milan and it was only $1190. Does this sound about right? If flying in and out of Milan is the way to go is it ideal to spend the day there to experience the city some and then get on a train later in the day/evening to head for Venice? Or would it be better to just stay one night in Milan and head for Venice early in the a.m the next day?

  • Eric

    Hey Jessica, thank you so much for posting all of this incredible info on Italy. My wife and I are traveling to Italy and following an itinerary similar to the one you proposed on the 2-weeker… flying into Rome and out of Venice (mostly due to flight costs… just worked out that way). We’re getting ready to book hotels and such and I had a question on the inter-country train lines. Do you recommend we book train tickets ahead of time or is it like other European nations where you pretty much walk in day of (at least knowing the schedule a bit) and just hop on and go. And… is this the correct website: to do our planning? Thanks again!

  • Jenna

    Hi there – great article! Do you recommend certain books for Italy that offer self-guided walking tours? We’re visiting Amalfi, Florence and Venice in September, and I’m looking for walking tours we can follow with trivia/fun facts/holes-in-the-walls, etc. Thank you!

  • Tiffany

    Hi Jessica. I really enjoy reading your articles and travel advice. It’s been so helpful in planning our upcoming trip to Italy!

    I’m just curious why you recommend traveling from Venice to CT to Florence, instead of Venice to Florence to CT since Florence seems to be “on the way.” Is it easier to get to Rome from Florence than CT?

  • gina touchton

    Six of us are traveling to Italy in October 2013. We are flying into Rome staying over night and then going by rail to Cinque Terre. We plan to stay there 2-3 nights. Went on-line to see about housing and it seems that we could rent a flat much cheaper than staying at a hotel. Do you have any recommendations as to which town to stay in and also any suggestions about our housing. We plan to then go to Florence for a week and will end up in Rome for the remainder of our stay. Again we would like to stay in an apartment in both cities. We know we want to stay in the Oltrarno when in Florence and have no idea where we want to stay in Rome. If you have any suggestions about where to stay and have any contacts in regard to renting an apartment I would appreciate it. Thanks
    Gina Touchton


    Hi, I am from India and presently in Mareille, France. I would like to visit ITALY this month for a week’s time. Can you please make me an itinerary for the same as in which cities to see and what places, with the information of the trains timing and fare with global Eurail pass. We will start on 22nd Feb and would like to return on 28th Feb. It would be great if you can give me the information for youth hostel and their booking procedures as well.
    Waiting for your reply.

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