Italy Itinerary: A Perfect Two Weeks

Italy map :: creative commons photo by Nicola

Italy map :: creative commons photo by Nicola

For as long as I’ve been writing about travel in Italy, I’ve gotten questions about Italy itineraries. When you’re so spoiled for choice, it can be hard to pick an itinerary that eliminates places you thought were “must-see” sights. But with a limited amount of vacation time, those are the hard choices that must be made. That’s why I’ve put together what I’m calling the perfect two-week Italy itinerary.

Find out how I make my own travel plans so you can tailor your trip to your exact needs with my article on how to create the perfect Italy itinerary for any trip.

The Italy itinerary you see below is quite similar to the itinerary I created for my own first trip to Italy many years ago. It’s ideal for first-time Italy visitors who don’t want to miss the highlights but may also want to add on a few other options for side-trips.

Here’s a brief look at my suggested two-week Italy itinerary, with more details below:

To avoid back-tracking geographically, your best option is to get an open-jaw ticket flying into Venice and out of Rome. Open-jaw tickets are often competitively priced with airfare that’s in and out of the same city, so they’re always worth considering. When your other choice is to back-track, an open-jaw ticket means you’re using your vacation time for your vacation wish-list – not in transporting yourself across the country. I’m all about efficiency, and I want you to have as much time as humanly possible to enjoy Italy (and not just its train system).

Speaking of the trains, this itinerary is easily do-able entirely on public transportation – trains and buses – so you don’t have to worry about renting a car or driving in Italy.

You could do this itinerary in the reverse order, starting in Rome and ending in Venice, but I recommend Venice as a starting point for any Italy trip that includes Venice on the itinerary – and particularly first-time visits to the country. The Venice airport is far smaller than Italy’s two major airports – in Rome and Milan – which means it’s easier to navigate, and there is absolutely nothing like having your first Italian experience be the surreal city on water. Approaching Venice from the airport on the mainland, gliding across the lagoon on a vaporetto or water taxi – well, there’s nothing quite like it.

Another reason I like Venice as an introductory city in Italy is that its lack of cars means the average tourist, gazing up in awe rather than looking where he or she is going, won’t get hit by a Vespa. In Venice, the worst that can happen if you’re not watching where you’re going is that you’ll fall into a canal. By the time you get to Florence, the “HOLYWOW I’M IN ITALY!” feeling should have dissipated a bit, so you’ll be better-equipped to pay attention to traffic.

One final note, before I dive into the itinerary details: Before anyone gets annoyed by something I’ve left out (or included), please read my caveats at the bottom of the page. After that, if you’re still upset, by all means let me know.

Venice – 2 Days

Venice at night :: creative commons photo by Iselin

Venice at night :: creative commons photo by Iselin

You’ll begin your Italy trip in Venice, one of my favorite cities on earth, in what is likely a flight arriving in the morning. Venice doesn’t have a real off-season. It’s always somewhat crowded, and that doesn’t stop it from simultaneously offering quiet and romantic corners. Many travelers think that by visiting Venice as only a day trip that they’re avoiding the worst of the crowds, but Venice is at its most busy during the day specifically because of the day-trippers and cruise-goers. By staying at least one night in Venice, you give yourself a chance to enjoy a city that can be difficult to love.

Venice has a few attractions that most people think of as “must-see sights,” but the main thing to do in Venice is to simply wander, explore, and get lost. And because the island is quite small, you can easily cover the whole of Venice in a day. Going into churches and museums then becomes easy to add to your itinerary.

Aside from aimless wandering, Venice’s main attractions include St. Mark’s Basilica and piazza, the Doge’s Palace, and the Rialto Bridge. Venice isn’t a town known for its nightlife, but when the day-trippers have departed you’ll be able to take one of the best nighttime strolls of your life.

Venice’s Santa Lucia train station has regular service to destinations all over Italy and into the rest of Europe. After two nights in Venice, you’ll leave on an early morning train for your next stop in the Cinque Terre, which will likely include a transfer in Milan. The trip will take about 6-7 hours.

Read more about what to do & see in Venice

Cinque Terre – 2 Days

Vernazza :: creative commons photo by Pank Seelen

Vernazza :: creative commons photo by Pank Seelen

The secluded charm of the Cinque Terre is what drew visitors here in the first place. These five villages no longer feel very secluded, as they’re often crowded with tourists who come to hike the trails that connect the towns and to marvel at buildings that seem to grow right out of the rocks. The Cinque Terre has become one of northern Italy’s most popular places to visit, and – like Venice – is often a day trip destination. That means spending the night gives you a better chance of seeing the best aspects of the area.

You’ll arrive in the afternoon in the Cinque Terre, in time to settle into your hotel and explore that town. You may even have time to hop on the slow train that runs between the villages to explore another town in the evening, perhaps even having dinner there before heading back to your hotel or apartment. Spending two nights gives you one full day in which to do all the hiking you’d like to do – if there’s time the first afternoon when you arrive to do some additional hiking, that’s a bonus.

There isn’t much to do in the Cinque Terre besides hiking, lying by the sea, swimming, and relaxing – so take your time and enjoy your hike (best to go first thing in the morning before it gets too hot), cool off with a swim in the afternoon, and feast on local seafood for dinner.

After two nights in the Cinque Terre, you’ll take a train bound for Florence. Because the trip is only 2.5-3 hours long (even with a change in Pisa), you don’t need to worry about an early start if you’d rather go for a morning hike. If you’re planning to stop in Pisa for 1.5-2 hours to see the leaning tower, however, I’d recommend getting an early train so you’ll have time for a Pisa visit and still get into Florence for a leisurely evening.

Read more about what to do & see in the Cinque Terre

Florence – 4 Days

Florence Duomo :: creative commons photo by Rosino

Florence Duomo :: creative commons photo by Rosino

Florence could easily be the focus of a two-week vacation in Italy all by itself, and you still wouldn’t see everything the “Birthplace of the Renaissance” has to offer. With four nights in Florence and three full days, you’ll have enough time to see the major sights at a slightly more leisurely pace and squeeze in a day trip if you so desire.

The “must-see” sights in Florence include the fabulous Uffizi Gallery, the Accademia, the pretty Ponte Vecchio, and the multicolored Duomo – but the list doesn’t end there. The good news is that the bulk of the city’s main attractions are concentrated in its historic center, which means that although this will be your first taste of Italian city traffic since your arrival in the country, you’ll mainly be focused on the parts of the city that are more pedestrian-friendly than they are choked with cars.

Since you cleverly stopped in Pisa en route to Florence, if you’re itching to see the Tuscan countryside before heading south to Rome then I’d recommend a day trip while you’re in Florence. Siena is perhaps the most popular day trip destination from Florence (after Pisa), and although it’s a large city now, there’s an historic medieval core that’s quite appealing. It’s the sort of place people fall in love with instantly, and when you get there you’ll probably understand why. Another popular day trip option from Florence is San Gimignano, a small walled town with a plethora of medieval towers. Both Siena and San Gimignano are easy to reach from Florence by bus. Keep in mind that both are popular day trip spots, which – like Venice – means they’re extra-busy during the day. If you can’t spend the night in either city, however, then a day trip is the next best thing.

After four nights in Florence, you’ll board a train the next morning bound for Rome. It’s a 2.5-3 hour trip.

Read more about what to do & see in Florence

Rome – 5 Days

Looking toward Vatican City from Rome :: creative commons photo by Nicola

Looking toward Vatican City from Rome :: creative commons photo by Nicola

Even without ever having set foot in Rome, no doubt you know just how important the city is – and has been – for more than two thousand years. Even with the gravitas of all that historic significance, Rome is very much a city on the move – a modern metropolis with no time to slow down for visitors. I’ll admit that the first few times I went to Rome I found it to be overwhelming and exhausting. I’ve come to respect Rome, and I’ve learned to love it, but it didn’t come easily.

Rome is big. It’s sprawling. (The bus/metro/tram network is intricate. Get to know it – it means you’ll avoid exhausting yourself by walking everywhere.) One of the things that helps immensely is giving yourself enough time to ease into Rome rather than trying to see everything in two days. Having five days in Rome means you won’t punish yourself with an overly-ambitious itinerary. You can go back to the hotel room for a midday break if you need it, or spend an extra hour in a piazza watching the fountain and eating gelato. In short, don’t beat yourself up about trying to “conquer” Rome. You’re on vacation, remember?

The “must-see” list in Rome is extensive. You can see the major sights of ancient Rome – the Colosseum, Roman Forum, Pantheon, Capitoline Hill, and Palatine Hill among them – in a day. It’s best to give Vatican City the better part of a day. There are museums and art galleries to visit, markets to scour, and lots of great Roman cuisine to enjoy. You might be content to savor Rome for your four full days in the city before you fly home, but if you can’t bear to be this close to Pompeii and not see the famous archaeological site, you can do a day trip to Pompeii from Rome.

Pompeii is actually a much easier day trip from Naples or even Sorrento, since it’s so close to those, but you can do Pompeii in a day trip from Rome. You’ll just need to plan on an early morning train, and make sure you’ve researched the train connections ahead of time. You can also book a guided tour of Pompeii from Rome to leave the logistical wrangling to someone else.

You’ll fly home from one of Rome’s airports, and if you’re fortunate enough to have a flight that doesn’t leave at the crack of dawn you might have enough time to check something else off your to-do list in the Eternal City before you head out of town. Even though this is the end of your trip, you might consider bringing your Italy guidebook on the plane in your carry-on bag – you’ll be able to start planning your next trip to Italy on the flight home, picking up on the Italy wish list where you left off this time.

Read more about what to do & see in Rome

Aforementioned Caveats (AKA You’re Not Allowed to Send Me a Complaint About This Itinerary Without Reading These First)

I know some readers will have gotten to the end of the itinerary and will be horrified that I’ve left their favorite place off the list, or that I’ve included a place that they think isn’t worth the time. I hope these caveats will help explain why I made the suggestions I did.

“What’s perfect for you isn’t perfect for everyone.”

You’re right. It’s impossible for one traveler to tell another traveler what constitutes the “perfect” itinerary. We can make good suggestions based on what we know of another person, but in the end each person’s travel style is going to make it impossible for one itinerary to be a “one size fits all” trip. Having said that, there’s a reason the “tourist trail” is easily identified. Many travelers hit the same spots, often in the same order, because most people want to see the same highlights. My guess is that even if this Italy itinerary isn’t perfect for your first-time trip, you can probably make it perfect with a small tweak or two.

“Two weeks isn’t nearly enough time to see Italy.”

You’re right. And yet most Americans are lucky if they get two weeks of vacation time in a year. If you’re fortunate enough to get more vacation time, or if you live in a country that’s more generous with its holiday time, then feel free to use this itinerary as a starting point from which you can add more cities to fill the rest of your trip. If you only have two weeks, remember that Italy will be waiting for your return.

“You can’t possibly say you’ve seen Italy unless you see (fill in the blank).”

Oh, but you can. This is a sort of snobby attitude that one type of travel (and traveler) is better than another. I’m not fond of that attitude. Just because you don’t visit all the places on someone else’s idea of a proper Italy must-see list doesn’t mean your trip somehow “doesn’t count” or that you didn’t do it right. Of course, if you only set foot in Italian airports on your way someplace else, then – yeah – you can’t say you’ve been to Italy in that case. Even I’ll call you on that one.

“Don’t bother going to (fill in the blank), it’s just a tourist trap.”

As mentioned, tourist traps often become tourist traps because there’s something cool to see or do there. No, you’re not the first person to snap a photo of yourself propping up the leaning tower of Pisa. And if you really want that photo? Then, by all means, go for it. There’s nothing original in my affection for Venice, and no one can convince me I shouldn’t love the city just because it’s often overrun with tourists.

“Oh, you can cover way more ground in two weeks than that.”

Spot on. And I always choose quality vs. quantity when possible. I have a thing when I’m planning my own trips and I make the same recommendation to many other travelers – stay at least two nights in every place in every case where that makes sense. Changing hotels every day can get kind of exhausting, so that your trip becomes one endless stream of reception desks. I’d wager most people don’t want that to be their vacation theme.

59 responses to “Italy Itinerary: A Perfect Two Weeks”

  1. Hi
    It’s my 40th in 3 years time and I have never been to Italy this is my wish for my birthday. I would love to see Rome, Verona, Pompeii and a place called Puglia and have dinner in the restaurant nestled within the sea cliff. I suppose I am basing my wishlist on movies that I have seen like Letters to Juliett the countryside looked so magnificent and I have fallen in love with it. I would have 3 weeks maximum is it possible to complete my wishlist in this time.Please any suggestions would be grateful.
    Yours sincerely

    • Jessica says:

      Thanks so much for your comment, Geraldine! I’m actually working on an article that will help anyone craft the perfect itinerary for their trip, no matter how long it is or what’s on their wish list. Look for it in the coming weeks (if you’re subscribed to the newsletter, you’ll be sure to see it).

      In the meantime, I’ll tell you that with three weeks, you could definitely see quite a bit of Italy – it’s just a question of how much time you’d want to spend in transit. Puglia is a region of Italy – it’s basically the heel of Italy’s boot – and quite a distance from the other places on your list. So, it could definitely be done, though it would depend on how much time you wanted in the other places you’d visit and (again) how much time you’re willing to spend getting from one place to another. As a starting point, I’d suggest you get out a map of Italy so you can see the distance from Naples/Pompeii to Puglia, and then check out things like train times/costs and flight times/costs to get a rough idea of the time and expense in traveling that distance.

      • Thank you Jessica I will keep an eye out for that information. Do you in your opinion think that the puglia area is worth a visit?

        • Jessica says:

          Well, I think pretty much everywhere in Italy is worth a visit. 🙂 Honestly, though, I’ve not yet been to the Puglia region myself, though I hear rave reviews from friends I trust. I think the real question is what in Puglia is making you want to visit? Is there a particular place you’ve read about, or a photo you’ve seen…?

          • Yes a picture of a restaurant in a cliff face it’s a hotel also. I love places that look beautiful that have countryside and sea meeting the land. I think I want to experience real Italy maybe for my first trip.

          • Jessica says:

            Okay… Italy has so much coastline, it’s possible you could find the same sort of atmosphere/scenery (though not that exact place, obviously) in another part of the country, too. Just a thought, as you’re looking at maps and transit times, to keep in mind in case you don’t want to go as far as Puglia after Naples.

    • dt says:

      in Puglia it’s the Grotta Palazzese Hotel in Polignano A Mare
      the restaurant is built into a cave under the hotel.

  2. Stephanie Rose says:

    HI Jessica! Thanks for all the great info. We are leaving for Rome IN LESS THAN TWO WEEKS and we’re still not sure where to go after Rome. We’re trying to loosely follow your itinerary, except flying into Rome on April 19 and out of Venice May 2. We have places booked in Rome until the 21st and Venice from the 31st to the 2nd. My husband wants to see Cinque Terre, and we have tickets to the Uffizi on the 24th (so Florence will be in there somewhere.) That’s all the planning we’ve done. Want to help us fill in the gaps? We’ve gotten day trip suggestions of Lucca, Siena, and Assisi from family/friends. 🙂

    • Jessica says:

      Hi, Stephanie – thanks for the note! It sounds to me like you’ve got a great start to your planning. Your Rome visit is pretty short, so I’d suggest booking a guided tour to see the main sights efficiently.

      Siena is an easy day trip from Florence (take the bus, it’s faster), Lucca can be as little as 1 hr 20 mins from Florence by train, & Assisi is at least 2.5 hrs from Florence by train. So if you want to stay longer in Florence to take day trips, I’d stick to Siena & Lucca just to avoid being on the train too long.

      Cinque Terre can be done as a day trip from Florence, too, although I’d recommend an overnight (or two) out there instead – especially if you’re wanting to do some hiking.

      If you’d like to add another stop along the way & not just split the remaining time between Florence & the Cinque Terre, you could stay a night or two in Assisi or Bologna, or stay in Siena for a couple days instead of making it a day trip from Florence.

      I hope you have a wonderful trip!

  3. Alyssa Carney says:

    Hi, Jessica! Thanks so much for info it really is the perfect itinerary! I’m taking my senior trip to Italy next May and I’m using your itinerary but we are going to end up having 2 extra days. I’m going to use one of them to take a day trip to Verona from Venice but I’m not sure what to do with the other day. Any suggestions?

    • Jessica says:

      Thanks for the kind words, Alyssa! You might consider altering the itinerary a bit to spend three days in Florence and two in Siena, giving you a chance to see that city on an overnight trip (stay in the historic center). You could also just tack on another day’s stay in Florence and take another day trip. Day trip options from Florence are plentiful – San Gimignano, the Chianti region, Bologna, Cortona, Assisi… Just Google a few of those places to see if any of the descriptions catch your fancy! With another day in Rome, you could day trip to places like Orvieto, Ostia Antica, or Tivoli to see Hadrian’s Villa. Have a great trip!

  4. Sherry White says:

    Hey Jessica, that’s a good itinerary to follow. And its the 2nd part of your article that I liked reading. You have explanation for everything :). But I agree with you, how one’s idea of perfection can be the same as someone else’s.

    I am not fortunate enough to follow this itinerary as we do not have 2 weeks but just 2 days which we have decided to devote to Venice. As this is my first trip to Italy I want to see all those world famous attractions and take a Gondola Ride, so I decided to follow an itinerary, which leaves a lot of scope to take a walking tour of Venice. I am not sure I will be able to experience Venice in just 2 days, but will follow your advice on the nighttime stroll. Hope to have a good time there.

    • Jessica says:

      Well, since Venice is one of my favorite cities on earth, I think you’re making an excellent choice. Two days in many Italian cities wouldn’t be enough time to see much, plus you’d be rushing around, but in Venice two days gives you time to see the major sights in a relaxed way AND have plenty of time to just wander aimlessly. I really hope you enjoy the city!

  5. Sherry White says:

    Thanks Jessica! Next time I go to Italy will sure plan for a much longer duration and try to cover much more cities. Will keep on reading your blog to plan for a perfect trip to Italy.

  6. Heather says:

    I am taking my 2 adult sons to Italy in January where should we stay? Hotels, rooms etc?

    • Jessica says:

      Hi, Heather! Are you asking whether you should stay in hotel rooms or rent apartments? Or are you asking about what specific hotels to stay in? If it’s the latter, I don’t do travel planning to that level of detail (my friend Madeline at Italy Beyond the Obvious does, though, and she’s wonderful). If it’s the former, I think it depends partly on your travel style. Hotels are much more full-service, but you won’t have as much privacy with three adults in one room, so you’d spend more for multiple rooms. Apartments/vacation rentals offer multiple rooms and kitchens and other amenities, but you won’t get room service or a concierge. Does that help? Or am I missing your question?

  7. Amanda says:

    Hi Jessica, Thank you for sharing this itinerary! My husband and I are planning our first trip to Italy next year for 2 weeks. I think we will follow your itinerary…however the plan was to stay in CT only 1 night, and 3 nights in Florence. Do you have any suggestions for the 2 days saved? Would Sorrento be a good option?

    • Jessica says:

      Hi, Amanda, & thanks for your note! Personally, since it sounds like you’re already moving around quite a bit, I’d suggest someplace a little more in the path of your existing itinerary (Sorrento might be more time in transit than you’d like). If you haven’t already looked at my tips for creating the perfect Italy itinerary, I’ll direct you there. And, if after you read that you’re totally okay with the transit times involved in adding Sorrento, then by all means go ahead! I just like people to know that stuff beforehand. Other options you might consider if Sorrento turns out to be too far away are: Perugia, Assisi, Orvieto, Siena, Verona, Bologna, or Genoa. Those are more or less “on the way” or very close to places you’ll already be visiting.

  8. Keshav says:

    Hi Jessica,

    Season’s greetings and warm hellos from India!

    To get away from my busy work schedule, I have booked my travel to Italy (28th Dec to 10th Jan) – a country that I have been super excited about (Italian food, oh gosh! I am vegetarian – but the Italian desserts, pasta and pizzas are yum!)
    I have been to France, Germany, Belgium and Netherlands in the past. Yes, safe to say that I love Europe 🙂
    I know this isn’t the best weather or time to be in Italy.
    Plus, I am flying in and out of Rome. Quite apparent that I didn’t do much research before booking my tickets on an impulse to get away!

    I have booked myself in a Rome hotel from the 28th Dec night to 3rd Jan morning. Also booked to see the Nutcracker ballet on the 31st Dec, a Colosseum tour and Vatican city tour on 2nd Jan 🙂
    Rest all undecided! Open to day trips from Rome!

    Your blog has given me hope!
    You seem to have a pulse on my mind… Haha!

    Please suggest how I should utilize my 12 days in Italy. Need to book hotels and travel accordingly!
    In you, I see God 🙂

    P.S. – I am travelling single as a 34 year old businessman who loves culture, performing arts, nature, walks, hot men (*wink*) and history (to an extent!)

    Apologies if that’s a tad much.
    Hope to hear from you!
    Many thanks!


  9. Deb says:

    We are traveling to Venice, Cinque Terre, Tuscany area and then Rome. After looking at the train schedule I would be saving time going from Venice, Rome, Tuscany and then Cinque Terre. It is a 6 hour train ride from Venice to Cinque Terre, but I can take a fast train from Venice to Rome in 3 hours. What is your opinion about this?

    • Jessica says:

      Without investigating transportation times myself, I’d say that if you’ve found that going to the Cinque Terre after Tuscany is fastest then go for it! You didn’t say whether you were flying in & out of the same city, so just remember to consider transit times back to your departure airport, too.

      • Deb says:

        We would depart from Pisa

        • Jessica says:

          Really, any itinerary is fine as long as you know what you’re getting into, I think. So if you’re aware of all the transit times involves, then go for it – backtracking to Pisa from the Cinque Terre wouldn’t take nearly as long as going back up to Venice or down to Rome, that’s for sure. 🙂

  10. Lisa says:

    Hello Jessica, I was hoping for your insight regarding the rail system in Italy please. I have a trip booked including (2) nights in Venice, then (2) in Florence, (2)in Lucca, (3)in Vernazza and finishing with (3) nights in Rome. I plan to travel between the cities solely by train. Is there an issue with the trains booking up well in advance? I see one can order tickets online in advance but I find that a little difficult to do, not knowing exactly when to leave one city for the next before even arriving. Most of the check-outs are at 10:00am so I was thinking of booking the 13:00 or 1pm train so even the longest train ride to Rome, I would arrive 17:00 or 5pm. Your thoughts please?

    • Jessica says:

      Hi, Lisa, & thanks for the note! First off, I would of course recommend my ebook all about the Italian rail system – ITALY EXPLAINED: ITALIAN TRAINS. 🙂 Some routes do get quite busy, especially during the high season. As for when to leave each city, that’s entirely up to you. There are trains on all those routes on a fairly regular basis, so it’s just down to whatever time you’d choose to leave one city or arrive in the next. You know in advance that you won’t have time to see or do everything in each place, so don’t stress out over gaining or losing another 2-3 hours unless there’s a museum only open on that day or a special event going on. I hope that helps!

  11. MB says:

    Hi Jessica

    We are a family of 4 (incl 2 teenagers) planning a 1st time trip to Italy for 2 weeks. 12 days there – 2 days flying. Flying into Venice and out of Rome. I was thinking 2 days in Venice, 4 days in Florence ( 2 to see city, 1 day trip to Pisa, 1 trip to Tuscany/Chianti) and 4 days in Rome – 2 days city, 1 day Vatican and 1 day Pompeii. I have 2 additional days – don’t know where I should use them. Should i add 1 day each to Florence and Rome or 2 to eone of them? So confused…

    Your thoughts?

    • Jessica says:

      Hi, MB, thanks for the note! I’m smiling, because this is almost exactly the itinerary I’ve got planned for my boyfriend & his family in March. They’re flying in & out of Milan, so that’s where their other two days went, but otherwise they’ve got the same duration in each city. So obviously I think you’re on the right track! 🙂 I honestly think you can spend four solid days in both Rome and Florence & not see everything, so adding one day to each of those would give you another day of exploration (especially in Rome, where taking a more relaxed pace is often a good idea). You could also add another destination altogether, say a Tuscan town like Siena, to get the Tuscany experience in a 2-day stay (thereby giving you a day back in Florence itself).

      • MB says:

        Hi Jessica thanks for you feedback. I am going with your recommendation – 6 days in Florence (4-5 to be precise) One day getting in early – last day leaving for Rome. I was wondering if I was being too ambitious with this itinerary –

        D1- Florence. D2 – guided tour of Siena, San Gimignano and Chianti, D3- Luca and Pisa, D4 – Cinque Terra, D5- wine tasting in Montalcino and Montepulciano, D6 – leave for Rome.

        Would you do this differently? I would love to get your thoughts-

        • Jessica says:

          Well, I suppose it depends on how much you actually want to see/do in Florence itself. Since all but one day are listed as day trips in your itinerary, you’ll either need a very well-organized day in Florence to see all the top museums, etc. – or you don’t have all of them on your wish list. 🙂 So it really depends on what all you want to do in Florence.

          • MB says:

            yea you are right – need one more day in Florence. Added one extra day!! Down to 4 days in Rome. 2 days city, one day Vatican and one day Pompeii

  12. KJ Nutter says:

    Planning a trip for the 2nd anniversary of my 30th Birthday Sept 25-Oct. 15. Flying in and out of Rome. My personal dream is Positano so this is throwing off our itinerary. I figured 3 nights in Rome. Travel to Sorrento or Positano next. Trying to figure out which should be 1st. We can go to Ravelli etc from Positano then to Sorrento. From there to a day trip to Pompei and overnight trip to Capri. Then, Tuscany/Umbria area(Assisi,Sienna,San Gimignano ), onto Florence for a few days w day trip to Venice then back to Rome. Or Rome to Sorrento, Positano, Tuscany, Florence, Venice, Rome. We have 18 days total and I’d like to make the most of it. Should I skip Sorrento and go to Capri and Pompei from Positano? Stay in Sorrento 1st and take those trips then on to Positano? Thanks for any suggestions!

    • Jessica says:

      Thanks for the note, KJ! I would first refer you to my article about how to create the perfect Italy trip, no matter the duration or where you’re going, which is based partly on researching transportation so you see how much time you’ll spend getting to/from stuff you want to do. I think that’s going to be key for you in determining whether you want to stay in Sorrento, Positano, & Capri – or only one or two of those places (since they can all be day trips from the others, really). If Positano is your dream, perhaps you’d be happier staying there longer & visiting Sorrento as a day trip? Again, look at transportation options/times (especially given your travel dates, some of the boat schedules may be less frequent or stopped altogether) so you can weigh what you give up with what you get.

  13. andrew says:

    Hi Jessica,
    my wife and i are going to italy for 15 day this in rome stay the night then venture south to sirenio to visit family for a couple days. work our way back up and then home. i know its the old you gotta see this and that.
    we want to see the colleseum , trivi fountain,pauls cathedral spanish steps, romantic boat trip in venice the vatican, leaning tower and amalfi coast. any ideas and or any other suggestions

    • Jessica says:

      Thanks for the note, Andrew! I’ll first send you to my article about how to plan the perfect Italy itinerary regardless of where you’re going. It sounds like you’ll need to research transportation times so you can weigh how much time you’ll “lose” in getting around, which lets you know how much time you have left. I’m not familiar with Sirenio, & I can’t seem to find it in an online search, so I can’t help with regard to getting there & back, but perhaps you already know? At any rate, depending on how long you want to spend visiting family & how long it’ll take you to get around, you’ll have a certain number of days left to play with as far as your wish list goes. I have no doubt you’ll have to cut something, if not a few things, but that’s always how it goes – you’ll just have to plan another trip! 🙂

  14. Jen says:

    What about the Amalfi Coast and Isle of Capri? I was thing there instead of Cirque Terre but dont want to make a mistake

    • Jessica says:

      It really depends on your schedule, Jen – how much time you have to get there & back, where else you’re going in Italy, etc. Read through my article about planning the perfect Italy itinerary, which may help you figure out the differences in logistics between the two.

      The Amalfi Coast & Cinque Terre are both collections of coastal villages, but they’re not identical, so perhaps you’ll want to read about the vibe of each to decide which sounds better to you, too.

    • andrew says:

      Amalfi and Cirque Terre are both very similar and very different. Amalfi coast is fantastic. Take the bus from positano to amalfi. You can purchase a ticket on the outside of the station in positano. The blue bus is your friend, but the ticket seller will show you the right way. the bus trip is slow as the road is long and narrow, but its half the fun. We were blown away by how friendly the people were. its not a hustle bustle town but more so a coastal town. lots of shopping and knick nacks if thats your thing, or lost of walking trails if you like the hill climbs. the resturants are all pretty good but we found a gem in the center square, to the left of the clock tower steps. A day trip to Capri is a great way to spend the day, me and my wife had a ball there for 3 days and aree going back next year to show the kids, although we are going to use sorrento as a base camp( this place is very nice too) Cinque is very similar but its 5 towns dotted along the coast. start at one end and wander your way thru all 5 towns. each has its own vibe/feel. we liked Amalfi more so we stayed there. coin toss.
      enjoy your trip.

  15. Shak says:

    Hi Jessica,
    my wife and i, along with my parents and our 2 year old are planning our first ever trip to Italy. After going through some weather patterns we decided May 2017 might be a good month as June – July get a bit hot and we’re thinking of renting an appartment. Now regarding the places to visit, we are all over the place! Our plan is to stay 14 days and definitely include Rome, Florence and Capri and a day trip to the Tuscany. Is there an itinerary that you could suggest that would accommodate old parents and a 2 year old and yet include the must visit places that i didn’t include? Also, would you suggest trains or flights? Last but MOST IMPORTANT, I’m trying to hopefully find a balance between travelling and relaxing on this trip. I’m hoping you can suggest something in between as i’d hate to go back exhausted 🙂 Thanks much

    • Jessica says:

      Thanks so much for the question! I think your first stop should be to read my article about how to plan the perfect Italy itinerary, because one of the main things to think about is how long it will take to get from place to place. That will not only give you a rough idea of how much time in a travel day will be taken up by traveling, it will also help you figure out the ratio of travel days to relaxing/sightseeing days. It’s one of the first things I recommend when trip planning.

      Only you know how much your parents will be able to handle in a day, whether it’s sightseeing or simply transit days. I will say that a kid’s schedule will force you to move more slowly (and therefore see/do less) than you would otherwise. That may help you relax rather than constantly be on the go.

      I’m not a travel planner, but if you want someone to do that for you my friend Madeline at Italy Beyond the Obvious is the person you want to talk to. Just tell her I sent you! 🙂

  16. Mary Grace Chua says:

    Hi Jessica,
    We are visiting Italy next year from April 13 to 29. Your itinerary sounds great and we will follow most of it! Thanks! I just have a question – we want to include some shopping like in the outlet stores and maybe Milan, which one do you recommend and can we include it in your itinerary somewhere? Is Cinque Terre worth trading for Milan in case there is not enough time? Thanks a lot again!

    • Jessica says:

      Thanks for the question, Mary! I’m not much of a shopper, but I know that there are day trips you can book to outlet malls outside Milan and Florence. Here’s one for Florence and here are a couple for Milan (those are affiliate links – I get something if you book, but it doesn’t cost you any more). As for trading Cinque Terre and Milan, obviously the two are VERY different, so it just depends on which experience you want more – coastal villages or shopping! 🙂

  17. Bren says:

    We are looking to do 15 days in Italy, have been to Rome and the Amalfi coast. Would like to do a short stay in Venice (our friends haven’t been)) head to Milan, Cinque Terre and spend a few days in the Barolo region on a vineyard. Any suggestion or guides would be greatly appreciated!!
    Thanks!!! Bren

    • Jessica says:

      You might want to start with my tips on planning the perfect Italy trip, no matter where you’re going. You could certainly spend a few days in Piedmont’s wine country, as well as add time at one (or more) of the northern lakes, or add Verona or Genoa… It all depends on what you all are interested in. If it’s primarily food/wine, then a wine-focused stay in Piedmont plus a food-focused stay in Emilia-Romagna would probably do quite nicely. 🙂

  18. kat says:

    Hi Jessica! I’ll be visiting Italy this November 2-11. That’s 10 whole days. This will be my first solo trip. I’m excited and terrified at the same time. Which cities should I visit? My friends mentioned Venice gets flooded that time of the year and not worth the visit. I’m most like to stay central – south Italy. I’m from Manila and don’t think I can brave the cold weather up north. Cinque Terre looks beautiful.

    Any help will be greatly appreciated.

    • Jessica says:

      Hi, Kat, and thanks for the comment. Though Venice is certainly not flooded all the time in November, (especially early in the month), it does get colder then – and foggy, which makes the cold cut right through you. You’ll have better luck with the potential for warmer weather if you go south, but even then you might run into rain. November is Italy’s rainiest month in most parts of the country. I’d look at Rome, Tuscany, maybe the Emilia-Romagna region. I love Naples, and it can also be challenging for first-time visitors, so do your research before you go if you want to add Naples onto your list.

      Check out my article on how to plan the perfect Italy itinerary no matter where you’re going, which should give you a game plan for researching where to go in early November. I hope that helps!

      • andrew says:

        ok my 2cents worth.While we had the best pizza in our whole trip in naples, i suggest you do your research well on this city.It was by far our least favorite place when we went to italy. Neighbourhood choice is everything. even in the expensive areas it still feels like little Sudan if you get my drift.Florence was fantastic( i can give you a awesome AirBNB person to stay with, its were we stayed, we were treated like family) Sorrento was just as nice too, but we loved Rome. I have Family in the south Reggio Calabria and it was a little warmer and a little less busy but the beaches were magnificent and the people super friendly.
        Hope that helps.If you want more info just email me
        Happy to help

  19. Jonathan says:

    Hi Jessica,
    Thanks you for all of the hard work and effort you have put into your website and answering your reader’s questions!! My wife and I have read it all and still feel we need some advice that you may be able to provide 🙂 We plan to be in Italy for two weeks mid to end of October and have already planned some parts of it but have some patches in the middle we could use some help with. We are traveling with our 7 and 11 year old kids. Days 1-5 we will be in the Venice region (Staying in Padua) and have already booked a place. Days 8-11 we are planning to be in Rome and are then departing from Naples on day 15. We have recently been to Tuscany (Florence, Siena, San Gimignano, Lucca, etc) and therefore would prefer to only pass through (hopefully stop to have an amazing nutella calzone in Calenzano on the way). After Rome we want to visit Pompeii, Herculaneum and possibly a day trip to the Amalfi coast. In any case, we are a bit overwhelmed by all of the options and we have not been able to decide what to do on days 5-7 (After Venice, before Rome) and then after Rome, where we should stay in the Naples area. We are planning Airbnb stays and have hired a car for the entire period (unlimited mileage 🙂 ). Any tips or suggestions would be greatly appreciated! (if anyone else reading this has an opinion, we would be happy to hear from you too!) Thanks! Jonathan

    • Jessica says:

      Thanks so much for the kind note, Jonathan! I’m glad my guide has been useful.

      Between Venice and Rome you’ve got a few options, especially since you’re driving. Umbria would be lovely. I don’t know when you’ll be there, but Perugia’s annual chocolate festival runs from the 14-23 of October this year. It’s a bit of a madhouse during that time, but it’s also chocolate. 🙂 I love Assisi and Orvieto, too. If you decide on Assisi, check out the apartments run by my friend Rebecca right on the main square. You could also stay in Bologna. If anyone in the family is into cars, the headquarters (and sometimes factories) of Ferrari, Lamborghini, and Ducati motorcycles are all nearby.

      I like the historic center of Naples, chaos and all. There are some notes on where to stay in Naples at the bottom of my Naples City Guide.

  20. Eva says:

    Hi Jessica

    Your article has been very helpful. We are using your itinerary for our 2 week trip, arriving in Venice on 26 Nov. Would you advise we keep the cinque terre portion? Both of us love being by the sea and happy to wonder around but we are not sure what to expect going there in winter. Do you know if we can still do a boat ride? Any insights to help us plan and prep for CT would be much appreciated. Thank you.

    • Jessica says:

      Hi, Eva, thanks for the note! I think the Cinque Terre in late November/early December might not be ideal, honestly. Winter storms there can be dramatic & beautiful, but there isn’t a lot to do that doesn’t involve being outdoors. (I’m not sure about the boat trips in winter, but I’d guess they’re high season only – or at least dependent on calm weather.) The towns aren’t very big, so there isn’t much wandering you can do before you run out of options. If you go anyway, look at staying in Monterosso al Mare (the largest of the five towns) or even nearby La Spezia instead of the Cinque Terre – it’s on the water, & it’s a bigger city with more wandering potential.

      Here’s more information about Italy in November & Italy in December for your perusal.

  21. Kathy says:

    do you actually offer a tour of some sort, or is the above just suggestions?

    • Jessica says:

      Thanks for the note, Kathy! I’m not a tour provider, no – I write this travel guide with the intention that people are planning their own trips. I do, however, have lots of links to tour providers on the site, mainly for guided tours of a city or attraction. Let me know if you’re looking for something specific, & I’ll see if I can point you in the right direction.

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