I would get a train pass and do it that way, rather than a group tour. That way, you and your son can set the pace and stay longer in places you love and less time in places you don't. You can also just pick a random little town and get off the train for the day and explore, which is so much fun.

I am a very dependent traveler (i.e. for most of my life, I've had my parents and then my husband figure out all transportation and logistics on trips) but when I toured Italy for 3 1/2 weeks in college, I was w/ another girlfriend and I was able to figure out the trains very easily... so it is not hard at all) We just had a small bag each w/ us and found inexpensive cute hotels when we got to each place, no advance planning- that would be a real adventure for your son if you are up for it!

IMO, Venice is not to be missed. It was by far my favorite place in Italy, without question. I hated Florence, I loved Rome, and I thought Milan was wonderful. We were in Italy the week before Christmas and I would highly recommend going at Christmas time. It is amazing to see everything all beautifully decorated.

You are going to have such a great time! I've been to tons of places in Europe and Venice, Rome and Milan are by far my three favorite cities! I would try to definitely do 10 days if you can.

You will love Italy. DH and I took a 10 day tour . We felt we would get to see so much more this way than alone. We figured we would go back to the places we loved. I agree with beagle, Venice was one of our favorite places, second was the Vatican.

We loved the Vatican too. We went for Sunday mass (watched outside on the big screens). We're not religious at all, but it was a great experience to watch all the people there to hear the mass (we did not stay for the whole thing)

beagle, I can understand why you didnt stay for the whole mass.....

I did a summer session at Cambridge and traveled in England mostly with other students, but a bit by myself. I have also been to Okinawa, Paris and China with varying degrees of doing the planning myself. I am usually the travel planner. A tour didn't really occur to me, because I have never traveled that way.

So I'm open to the idea of a train pass and organizing the trip myself. I wouldn't be able to bring myself to go without hotel reservations, especially with ds along--he's an anxious kid and if we had trouble finding a room he would find that very stressful. I am also definitely not up for driving in Italy. Oh and we can pack lightly. I once went on a two week business trip carry on only! In fact I went carry on only nearly everywhere until I had kids.

I was thinking Venice was a definite yes because with climate change, I'm not convinced it will be there for ds to go see in thirty years. Rome seems like a must? And I know he's really interested in the leaning tower of Pisa. Hmm, I need to spend some time looking at a map?

If it's a Christmas trip, I think it has to be Christmas 2016 so we can save the money. I think Christmas sounds lovely, but it would be awfully neat to take him for his birthday. And then I wouldn't miss Christmas with my youngest.

Thank you!

Cinque terre - it's a world heritage site on the Mediterranean. It's 5 villages built right into cliffs and you can hike between them or take a local train between. Try to go there google. Seriously gorgeous and I think a 13 yearold would think it was cool. You can take the train easily from there down to Rome.

I did a summer session at Cambridge too :) I wonder if we did the same one.

Yes, I would not miss Rome (I think you have to see the Vatican and the Colosseum would be interesting for your son)

Beaglesdoitbetter, downing college for law school?

Nope. Cambridge College Program. I guess there are lots of them probably...

Getting to all of those places can be a haul in 7 to 10 days. Trains are great way to explore Italy, but strikes and disruptions happen, so be aware. The train stations do tend to be central, but the areas surround the Central Stations tend to draw pickpockets, but also have lower cost accommodations. (I lived in Switzerland and DH lived in Italy)

I'd enter either at Milan or Rome, to cut down on your international connections. Do Rome for two to three days, and then take the train to Florence. Hit the main sights (David, etc) and then rent a car or take the train to Pisa. (I find driving in Tuscany far easier than say, Naples. In general, car driving gets worse the farther south you go). By car, you can hit Siena and Pisa. Back in Florence, you can take the train to Venice. After Venice, there is a high speed train to Milan. You can catch a return flight from Milan or connect back through Rome.

Sicily is a pretty big place to hit -- I'm surprised he would want to go there. I'd also consider: Naples/Pompeii (way cool for a 13 year old to see the buried city) and the Cinque Terra.

I'm really not a fan of Venice, especially in the early Winter. it is Acqua Alta time and the streets literally flood with not-so-nice canal water every day. It's still worthwhile, but just keep this in mind.

RoseAbbey, which tour company did you use? Would you recommend them?

How fun, and how great to have that one-on-one time! I have no advice, but I think it's an awesome plan, and I hope you have a wonderful time. I'd love to do the same with my son someday. I would definitely need a tour guide. As much as I love going new places, I'm an anxious traveler.

I should probably add that ds is very into the food. And has read every guide book on Italy we have given him. . . .

I think the train pass is the way to go. You can always do half day bus tours on the first day in each city to get your bearings and an overview of the city. It's been many years, but Florence was my favorite. I would do Florence, Venice and Rome if time is limited. It could be cold at Christmas, I might lean toward spring break.

When we took the kids to Europe we wound up in Italy and then Rome in the middle of July and yes it was hot but not unbearably so. I would rather go then than at Christmas.

As an aside, my younger son was teaching skiing in Japan one winter and after ski season my DH went over and met him and they spent 2 weeks, just the two of them, traveling through Japan. They loved the "two of them" time. We were in the middle of major house renovations so I couldn't go and I don't regret not going because of the great time that just the two of them had together. I really hope you guys can swing this because it's something you will both remember.

Dh's comment about going in December was that it wouldn't be so hot.

I think ds could be persuaded to skip Sicily without too much pain. I think Pisa is a very high priority. That tower leans, you know. That has actually spawned an interest in traveling to other places with famous towers.

I'm guessing his/our priorities would be Rome, Venice and Pisa.

Anyone have experience with whether tours are more or less expensive? I'm guessing more, but maybe not?

Thanks!

You can google "average daily temp" and find out exactly how hot it is.

More or less expensive that what, exactly?

More or less expensive than doing the same basic thing on your own.

oh okay. Hmm, I don't know! I guess one thing is, in some cases it can be more certain? eg, if they cover all of your meals, you don't have to guess what the trip will end up costing?

I would guess they are in a position to negotiate lower rates, but I am not sure how much it would be offset by the costs of all the services they provide.

It will be warm in June -- but avoid July. Too many Americans and Northern Europeans on holiday. The Italians take their holiday in August; the coasts and mountains are packed.

You could consider staying at an agrotourismo in Tuscany. These are small inns located in farms where they serve meals made with food they grow. I agree about Pisa -- spend 20 minutes getting the required photos and then head out to stay/explore cities like Lucca or Siena.

I'm thinking package multi-city tours are more expensive. But that is from a biased perspective of a seasoned traveler -- the discounts they get never seem to pay for the overhead of the tour company and guides. They are more about convenience and comfort, if you are not used to traveling by train.

I agree that I would book hotels, inns, and pensiones in advance. It'll take the stress out of the situation of finding the right place to stay.

Here is a National Geographic family tour. Might be too pricey but it gives you an idea of what they recommend as a nine day tour and seems to have some of the places you want to visit. http://www.nationalgeographicexpeditions.com/expeditions/tuscany-family-tour/detail

I second Gooster's advice to book hotels, etc., well in advance. Do not count on just showing up and finding a place or booking a month or two out. With the internet, etc., the popular and good places are reserved well in advance.

I would also suggest you think about booking a half day city tour with a private guide. Well worth the money. You will be amazed how much you will learn and see with an experienced guide and he/she can tailor the tour to your specific interests. I have no financial/business interest in either but would recommend:

The Venice Experience <admin@theveniceexperience.com>, http://www.theveniceexperience.com/backstreets_with_choices.html

Absolute Italy (took a half day private tour in Milan - would have never been able to cover as much as we did without her, plus she showed us her own favorite "local places" that we wouldn't have found on our own. If you want to see "Last Supper" (highly recommend) needs to be booked in advance - they can do it for you.
Via Maggio 35
51025 Firenze Italy
(39) 055-212877
info@absoluteitaly.it

If you go to Pisa, the Duomo and Baptistry are worth a tour. The three buildings, church, baptistry and campanile, compose a beautiful public space. Your son might also enjoy the museum Arsenali Medicei displaying an Etruscan and a Roman boat found during excavations for the San Rossore train station. If you visit Pisa from Florence, you might consider a stop at Lucca to walk or bike on the town walls, last modified by Napoleon.

I think your son would appreciate the uniqueness of Venice. The earliest settlement of the Venice lagoon was on the island of Torcello, a very atmospheric island easily reachable by water taxi from Venice. You have a feel for what the original settlement might have been. There are two wonderful small churches from the 11th and 12th centuries, and a bell tower that you can climb for a view of the lagoon.

Rome will have a lot to capture your son's imagination.

If you fly with a European carrier, say Lufthansa for example, after landing in Germany, you have a much wider choice of airports since it's no longer an international flight coming into Italy. You can fly directly to Venice, Florence, or the more convenient Milan airport of Linate instead of the distant Malpensa. Departing from a regional airport might also be more convenient than in Milan or Rome.

Completely agree with Duvetcover about some private tours. If you're thinking about Dec2016 you have enough time to explore sources and cost. You'll learn more than with a large group and will be able to personalize your visit. A half day a few times might be do-able. It would also be nice for your DS to have his own Roman to talk to!

Of course you must go to Pisa. Otherwise it would be the "place we missed", when it's one of your boy's main goals. Go, and take pictures, and give him all the time he wants! And don't even think of skipping Rome - one of the great cities of the world!

Unless you and he really, really want to see Venice, you might give some thought to Naples and Pompeii. Naples not so much, but you go through it to get to Pompeii. If your son is interested in Roman history, then actually seeing the place of the most famous volcanic eruption in history is almost a must. It is extremely dramatic, both poignant and beautiful. There, however, you would want to join a walking tour with a good guide; afterwards you could wander at leisure. There must be one-day tours from Rome to Pompeii.

If you've already thought of these ideas, forgive me for mentioning them. Has your son looked online for cds and dvds of lessons in Italian? He is the perfect age for tackling a foreign language and Italian is not difficult (I write this as a foreign language teacher). Again, with your timeline, there's plenty of time for him to learn a useful amount, even just in his spare time. Is he reading other things about Italy besides guide books? Watching movies set there? Is he interested in modern Italy or its Catholic aspects or ancient Rome? Or everything? So much material is available online.

WIsh I could be a mouse in your luggage! I adored Italy and if I could, would return to live there for at least a year. Not, however, ever driving a car, lol.

crl, the tour company was Globus. Yes we have used them twice. Once for Portugal and then Italy. Even the trip we are doing next week to the Azores, we are going with a tour. When we figured out the pricing as to going on our own and seeing and doing what is in the itineary, we found it was just a tad cheaper. If I was going alone with my son I would feel safer with the tour.

I'll make the case for a tour as well. We went with Tauck which was very expensive, but there are other, less expensive tours to take. But even Tauck runs tours designed for families so you may want to look into one of those. The beauty of a tour is that they handle all of the logistics for you. On our tour, they got us into the city and into our hotel (they took care of all the luggage) then gave us a half day tour in the a.m. of the city, then left us on our own to do what we wanted to do. When it came to Rome, one day they gave us a driving tour of the city in the a.m., and on another a.m., they got us into and out of the Sistine chapel and the cathedral with very informative guides who added so much to the tour, and then we were on our own for the rest of the time. Of course the tour guides were there to help plan what you might want to do on your own with all the information and guidance to get you from here to wherever....maps, places to eat, etc. They also do a spiel that is informative during the drive as well about the country, the customs, the history... My cousin loves to do the planning for her trips, so she would never take a tour. Me, I'd rather not be concerned and stressed with all the how to get from here to there, traffic and travel woes, etc....I prefer to "leave the driving to them."

As far as people, we have not had problems at all in the 6 tours we've done with them. In fact, we've met some very interesting people and have found that dining and riding with others adds to the experience and brings the familiarity of a ready-made "community" with you to a strange land.

I did really enjoy Venice the best, probably Rome 2nd, and Florence third. Milan was OK. (They were restoring the last supper at that time so we didn't get to see it...a big disappointment.) Florence gave me severe art overload...just too much to absorb. It got to the point that it was, "OK, another Boticelli, another Raphael, let's move on." I do have to admit though that even with all that art, Michelangelo and Da Vinci really stood out from all the rest.

I spent a semester in Rome when I was in college. Weather will be iffy at Christmas time. I arrived at the beginning of January and it was cold and gloomy. Mtn, you must be confusing Sicily with someplace else b/c it's not a city but an island and it's actually quite beautiful. My father's family is from Sicily-I visited my relatives there while I lived in Rome. They lived in a coastal town on the western side. There is actually quite a bit to see and do in Sicily, but it is far off the beaten path from mainland Italy and the other places the OP wants to visit.

As for Pisa, IIRC, you are no longer able to go into the Leaning Tower so you may want to check into that so your son isn't disappointed if he was planning to go inside. I've been to all the places your son wants to visit except for Milan--I overslept and missed my train by mere seconds. Fortunately several friends were in the station on their way to Pompeii so I tagged along with them. Loved Pompeii and would be very cool for a young teen boy to explore.

If you can afford it, I think you will need 10 days to see all the places on his list. Rome alone needs several days! And travel b/w the several cities will eat into your time, especially if the trains go on strike. Unless there is something in Milan he specifically wants to see, I might drop that from the list and instead try to add a coastal town in - you could head over to Sorrento from Pompeii and take a hydrofoil boat out to Capri (it's a quick ride). Or take a day tour of the Amalfi Coast. I was young and foolish and rented mopeds to drive half the Amalfi Coast--amazing but I wouldn't attempt it now! But you could either look for a day tour or take the local bus from Sorrento to one of the towns further down - I'm forgetting the name of the town we stopped in but it was right on the cliffs and spectacular. And if ds is a foodie and likes seafood, you can't beat this area for fresh seafood. Another coastal stop could be Viareggio, if Pisa stays on your list of places. It would be a fun beach day after visiting Pisa. I was there for Carnivale in March so didn't hit the beach itself, but it is popular as a beach destination in warm weather if you'd like to see the Mediterranean.

I need to go find my travel diary...I adore Italy. My daughter is going next summer with her Latin teacher. I'm still contemplating going as a chaperone as it's been nearly 20 years since I last visited. You will have a blast...and a trip for your son to remember. My dd went to Portugal with dh for her 13th birthday (SIL was getting married there). It was such good bonding time for the two of them. I was supposed to take ds somewhere for his 13th birthday last year but his busy summer prevented it. I think I was more disappointed! ;)

Thank you all so much!

According to ds there was a time period when you could not climb the leaning tower, but they did some foundation work and have since reopened it. I have not verified this, and it's possible whichever guidebook he is reading is out of date--though we have provided new ones to him.

And yes, we have discussed learning some italian. I thought we might start with an iPad app and see if our library has CDs we could borrow off and on and play in the car during errands.

I appreciate the tour company suggestions!

Thank you all so much!

I might just focus on 10-12 phrases and learn those well, unless you really think he is motivated to learn Italian. Its mostly for fun ....as everyone will speak english and, alas people will give you the menus in english, etc!

I think the tour question is a personal one. The places you want to see in Italy are very popular and very accommodating to tourists, you really dont need a tour. ANd while we often book tour guides for the day, I think of that as a luxury. Between the internet and guidebooks, you can be your own tour guide. An expert is better, yet, but its the first thing Id cut if I wanted to keep costs down. Heck you can use your phone as a guidebook!

One exception --- using a guide to get into certain places or avoid lines. The Vatican is a good example. Since we had a private guide, we waltzed right past the throngs standing in the sun waiting to enter.

Another way to get to the front of the lines is to purchase your ticket online and print it out. We were just in Europe and did this for many of the more popular attractions. When we arrived at the catacombs in Paris, the line was around the block, but we got in without waiting in the line, same for the London Eye and a few other places. We were in London, Paris and Venice and were a little worried that we wouldn't care for Venice. It was the last part of our trip and we absolutely loved it! We hired water taxis to get around, which was a splurge, because you can take the vaporettos (public canal transit) but it was well worth it and we all agree it was one of the favorite things we did on our vacation. Our hotel was at the other end of the island from San Marco so the ride down the Grand Canal was absolutely beautiful. I would not stay in or too close to San Marco as it is crazy packed with tourists.

Check out rick steve's stuff. I've downloaded a few audio tours of his, free on line, with maps, to take us through the Louvre, Musee D'Orsay and a walking tour of historic Paris. We'll share the ear buds off our iphone.

As far as learning Italian, I got by with yes, no, one and two, please and thank you. I learned how to ask "where is the bathroom", but ran into trouble as I couldn't understand the answer! Had I asked in English, they probably would've answered in English. Doh!

Also, they do have offline dictionaries you can download so you can have a handy "phrase" book with you.

We stayed right near San Marco square in venice and it was fabulous...we strolled the square at night and listened to the battle of the orchestras...it was so romantic! It also made sure we didn't get lost as everywhere there are signs to San Marco Sq, so we wondered around blissfully map free and never got lost. It is the best walking city ever.

Food will be the least of your problems in Italy. We look for restaurants that look homey & have a local crowd -- the food is usually great. One advantage of being American: the restaurant owners know we eat early and fast, so even if all the tables are reserved for the customary late-dining, lingering locals, the owners will let us have a table, say around 6 pm-ish, because they can make the quick turnaround sale and still serve their regular customers.

We like to travel by train from Rome, Venice, or Florence, and supplement with a rental car in Tuscany or Umbria or Emilia-Romagna or Lombardy. We had to get an emergency rental car in Perugia once when a planned bike trip proved to be more arduous then we'd planned for, the point being that traveling in Italy is fairly easy, flexible, & amenable to spontaneity (or emergencies).

We use Monastery Stays.com when possible. Quarters are clean with private baths, if somewhat Spartan. Sometimes there is excellent parking, and the locations areterrific, right in the heart of where you want to be. You'll encounter other international travelers also staying in the convents/monasteries. The situation is, not many people are opting for the convent/monastery life these days, so what to do with the rooms & real estate? Rent them out to travelers. We think it's a great bargain & have been happy every time we've booked a stay.
http://www.monasterystays.com/

AWM, what a cool idea!

We've taken tours primarily so the person who would normally be driving and looking at the road is able to actually see the scenery as well. That said, we have only ever had 1 tour with children. And that was a teenage girl with her mom. The young lady was obviously bored by all the adults.

European schools get out for summer in mid-July so any time before then is good to guarantee smaller crowds, lines etc.

The three cities you've chosen are good. Find hotels in central locations and then have all day trips on foot. As others have said, train between cities. Consider a Eurail pass for savings.

have a fun time planning!