This is doubly so with the kids along. Two one-week rentals would work well.

The weather in September is definitely better than in March, at least for Northern Italy: https://weather-and-climate.com/aver...ne,Milan,Italy
You could even end up with this in March: https://www.dreamstime.com/milan-ita...image111191489

With regard to the itinerary: this is definitely "chinese style", where you rush through, take a couple of pics, and leave again. If you really want to experience (and relax) a bit more, I would also skip some items and stay longer in others.
Maybe just do Milan / Venice / Tuscany (Florence) / Rome (in that order for logistics reasons). In Tuscany, there are lots of pittoresque little villages which you can check out (visually and food/wine wise !).
Going down to Naples / Amalfi (and back) will just add stress in my opinion.

A bit of advice about the beach, especially if you go to one in Italy. Pay for the private beach set up - the umbrella, lunge chairs, etc. Public beaches can be a mad house and it is just a nice bit of luxury at a not so steep price.

Thanks for all the advice. Normally we are pretty good about slowing down and just doing a few things. When I took my wife and sister to NYC we didn't see all the "tourist spots" however, I don't consider NYC our annual big trip. As discussed in other posts we aren't able to take as many trips compared to some of you. I still don't understand how a lot of you do it. Do you not own houses? Do you not have dogs or cats? Finding a dog sitter and house sitter is a nightmare for us, considering kids has made us as previous stated consider road trips over international travel. We spend about 30k a year on credit cards and a lot of those are welcome offer for the large amount of points. Are we missing something? That really is only good for 1 big trip and some smaller ones. We don't spend a ton on travel outside of points, so that might be the big difference.

What I meant by Lake Como being shutdown was the businesses surrounding it. I grew up with two local lakes and a river that had tourist coming to our area of the country quite often. However, it didn't have as much going tourist wise during the offseason and upon limited research I realized that Winter was still in effect in Northern Italy. So I figured it'd be hard to find a location to stay and experience some of the restaurants. Perhaps it is still a picturesque place to stop at for half a day??

Itinerary A

Milan(Arrival City) - 1 Day
Lake Como (Potential Half-day)
Venice or Florence - 2 days - Just to say we were there
Venice Or Florence - 5 days - whichever city we don't do for 2 days would get 5
Rome 5 Days
Pompeii 1 Day

That is a total of 14 days. Thoughts on this one?

Itinerary B

Milan - 1 Day
Florence or Venice - 5 Days
Rome 5 - Days
Naples/Pompeii/Amafi Coast - 3 Days

Itinerary C

Milan - 1 Day
Florence or Venice - 5 Days
Rome - 5 Days
Pompeii - 1 Day

I'm not sure where to place the last 2 days. Could do Florence or Venice 6 days and Rome 6 days. Could do some day excursions at a "home base" such as Florence or Rome. We could also skip Milan and wonder around it for a bit with luggage before heading towards our first "Home Base" and setting up shop for a while.

It is very hard based on our limited international travel for me not to want to toss in Venice or Florence for a day or two, just for my wife and I to say we were there once. We don't typical return to places that we have seen for our "big" international trips. We move to new locations each new time, so while we are open to reconsidering international travel with kids based on recommendations from this board. It could be years before we travel internationally again should we decide to road trip exclusively with kids or it could be years for us to return to Italy after this trip. Next on the list is Egypt, Japan, China, Paris and London. That is 5 years right there, that isn't mixing in my wife's preference for one big beach vacation such as the Maldives(Honeymoon location this year) every few years. So Bora Bora is on there, potentially Fiji and Tahiti(sp??). This would be 8 years.. If we didn't travel with kids that is 18 years before we could return..

I know this might all seem odd to you that we don't return for those of you who travel a lot. However, we haven't fell in love with a place that overwhelms us to return at the exclusion of new adventures or places. Anywho, I'm on a tangent now, my point is does any of these sound better from a slow point of view while also keeping our travel lifestyle somewhat in mind. We also aren't drinkers or foodies. So we don't normally go to places based on either of those.

Thanks!

Well yes, it is probably a difference in perspective. Most older and more experienced travelers are going to tell you to slow down, smell the roses, don’t try to see so many places in one trip. But we have all been you, taken many trips where we stayed at 5 or 6 places and now looking back think we should have made that two or three. It doesn’t mean we didn’t enjoy those trips, I know that I did. For myself, I made a trip something like yours, included a 2 night trip to Venice, and looking back if I were to do that trip again I would cut Venice out, save Venice for a future trip that might include Slovenia or Croatia. (Slovenia is great.) You are right it’s only three hour train ride from Milan and not very expensive so if that is what you want to do, go for it. If you are going in March I think it is sensible to stick to major cities because there is always something good to do there if the weather is bad.

I didn't go to Florence for the longest time. Finally went and loved it. BUT, what I loved were the museums. (Even though I have about a two hour limit for museums). If you go look into the Firenze pass. Best aspect is that I didn't have to wait in line (that may have changed).

Even though you've decided on Italy, I have an off the wall suggestion: Vietnam. Lots of stuff to see. There are temple ruins that are really neat. I'm a picky eater and hate fish and so I thought I'd starve, but the food is really good, even the fish. You can add a few beach days to the itinerary for your wife. I don't know if SE Asia will be open even by October of next year.

All of your itineraries have you ending with a day at Pompeii. While I think it is very much worth seeing (and to your question way back about Pompeii vs. Herculaneum - both can easily be done in a day (albeit a long one) but if you really want to choose one, I've always been more impressed with the ruins at Herculaneum), this is way out of your way considering your time constraints and agenda. If you absolutely have to fly out of Rome, as it sounds like you do, and you really are deadset on visiting Pompeii/Herculaneum, then I would fly to Naples from Florence or Venice (whichever you end up doing), and then head to Rome and end your trip there. This will be a smoother itinerary rather than worrying about getting back to Rome for your return flight.

I'll add one thing that I always consider when I'm looking into a trip and trying to decide how much to do - if it's a location that is very easy to travel to and has a ton of appeal, such as Italy, I prefer a slower itinerary because I know there's a decent chance I'll get back there at some point and can visit places I have not already. It's the harder to get to, more off-the-beaten-path destinations where I plan a much more active, tiring itinerary because there is a decent chance I won't get back there. Just something to consider.

I suggest a few things to consider:

1. 13 nights is not a lot of time to cover as much of the country as you are considering. Therefore, logistics really matter. Spend a little extra cash to make ground transport as easy and efficient as possible. For instance, instead of spending a day in Milan, when landing at Malpensa consider taking a car service directly to Venice. Yes, relative to the negligible cost of an award ticket it will be expensive but the convenience is totally worth it IMO. Or, consider flying directly to Venice. You can monitor award space for this option. And, even if fees are involved to change the tickets I think you will find very rewarding in the end
2. Think about what matters to you most and gives you the greatest enjoyment. Is it visiting famous museums and famous sites? Or does scenery really float your boat. I ask because while I am quite flexible, my spouse is okay with one or two museums and a couple of churches but otherwise really loves stunning scenery and quiet towns with "plus de charme".
3. Depending on your answer to 2), my suggestion is to focus on Venice, Florence and the Almafi coast. Venice is absolutely magical and normally swarming with tourists. Way off season actually plays into your favor, especially in the partial post covid world where mass tourisms will surely not be back to 2019 levels in Q1 2022.
4. Florence is very special and totally different than Venice. But splurge and stay in the very center so all sites are right outside your doorstep
5. It is early to visit the Almafi coast in March so weather is a risk. But the scenery is jaw dropipngly beautiful and very romantic. If you luck out with no rain then the advantage of going in March is avoiding the crowds, and they are legend. Normally I would suggest Positano but given your desire to visit Pompeii, Sorrento may be best. Personally, my favorite location is Ravello but that is not really suited for day tripping and is furthest away from Pompeii
6. You likely notice that I am skipping Rome. Obviously, it has its charms but it is very big city and after going to the museums and churches of Florence and the ancient sites at Pompeii/Herculaneum the Almafi coast is a nice balance as it is mostly about the scenery and local charm. Of course, if the Vatican is a must do for you then all bets are off. These are only my suggestions. I would suggest seeing if you can fly from Florence directly to Naples. The trains are perfectly fine but flying is quickest (see my note 1).

So, given the above I would do

1. 4 nights Venice, train to Florence ( you will be jet lagged so the first day or so will be tough, better to be lazy at first then ramp up the pace so while 3 nights in Venice is enough for me the extra night gives you the jet lag cushion)
2. 4 nights Florence, plane to Naples and car service to Sorrento Hotel (you can arrange via your hotel in Sorrento)
3. 4 nights Sorrento (of if you are so inclined Positano or Ravello), you seem very keen on the ancient sites, so you can a visit to both Pompeii and Herculaneum and I would not worry about sunburning in March
4. 1 night Rome airport (Fiumicino is a bit of haul from the city center so if your flight is pretty early better to stay at an airport adjacent hotel). I would also suggest flying from Naples to Rome for convenience.

Thanks! Will take everything under consideration. Important part is to travel again.

I realize that this is Flyertalk and everything, but I don't understand the advice being given to fly from Florence to Naples. (Assuming that you actually want to visit those cities and not just use airports as a jumping-off point.) The high-speed train takes only 3 hours, city center to city center and between Italo and FS (the two operators) there are lots of choices, schedule-wise. Are there even nonstop flights FLR-NAP?

Otherwise, I totally agree with all comments urging you to pare down. I'm never one of those dogmatic "Rome requires at least a whole week" people, but your itinerary will have you spending a huge chunk of time in transit.

A couple of other things that may have already been mentioned: If you really want to visit a specific museum, check out its closing days, if any. For example, if you're in Naples for one day, and it's a Tuesday, you can kiss goodbye to plans to visit the National Archaeological Museum. Similarly, forget about the Vatican Museums on a Sunday, except the last Sunday of the month, when they're free (and jammed). On the other hand, some of the biggies in Italy are open every day. Also, be aware that in the south especially, but also in other areas, many things including shops and historic churches close for several hours at lunchtime, so you may have less "usable" time than you imagine.

I'm currently planning my 12th trip to Italy, and I am by no means a high-salary individual. How do I afford it? Partly by staying in modest hotels, B&Bs, etc., that the average Flyertalker probably wouldn't consider staying in, by buying food at the salumeria or grocery store, by using public transit, etc. It works for me, but everybody's priorities (and financial circumstances) are different.

Good point about the high speed train service between Florence and Naples, if available.

My primary observation is, IMO, it is worth it to pay extra to keep the logistics quick and easy. While I find long distance train travel in Italy is very nice, the train stations themselves can be chaotic, with confusing signage and a bit stress inducing when it comes time to find your specific train and board with luggage (and I am guessing a 13 night trip will require at least a medium amount of baggage). I will never forget waiting in the Rome's Termini station for our trip to Naples. The track was not announced till very close to departure time and then it was a mad dash. And by then we had been in transit from the US for many hours as our entry point into Italy had been Milan/Malpensa. When planning the trip, a friend suggested having a car service meet us directly at Fiumicino and drive us right to our hotel in Positano. But the fee was well north of 350 Euros. We were penny pinching at the time so we rejected the idea. So, we took public transport from Fiumicino to Termini (itself a longer than expected schlep) and then a train to Naples and finally a cab to our hotel. It stretched out the journey by many hours and indeed was stress inducing. In making the mad dash to the train in Rome with luggage, a nicely dressed young woman appearing to work for the high speed train operator offered to help with luggage and find our reserved carriage and seats. How nice we thought! Well, when she demanded 20 euros per piece of luggage and would not leave until paid we understood how she really operated. We stood our ground, gave her a decent tip for the help and she backed off to find another rube. On the train ride back from Naples to Rome we knew the drill better and handled everything ourselves. But as we were getting settled, a nice elderly American couple entered our carriage looking quite pale and alarmed. Of course, I immediately asked if all was okay. They had encountered the same "service" that we experienced on the outbound journey when waiting for the train to depart Naples. The key difference was that the kindly gentleman offering to help took their train ticket indicating that he "needed" it to confirm that the couple was waiting at the correct location for the train---only to demand 150 euros from them before giving it back and letting them proceed. Of course, by this time the train had begun moving and there was nothing we could do. Moral of the story, nothing is as easy as it seems. So, when you don't know the language and understand there are a wide variety of trains operating on the same route with similar names, may be tired from travel and unfamiliar with the whole process, the journey can be somewhat stress inducing. To some, this is part of the experience and they shrug it off. For me, if I do encounter it, I accept as part of travel. BUT, if there is a way to avoid more complicated logistics by spending some money, I almost always select the most efficient option. I have traveled through Europe in recent years many times now. And I have found following this adage always is worth it to me in the end.

Japan, Italy and China are my top 3 most favorite countries, in the order listed. It is personal, of course.
China requires visa for US citizens.

Wanderlustfl. I appreciate the insights and this really helps..I have been doing train logistics and was like this can't not work. I hadn't thought of all the frustrating other part. I handle those frustrating parts during travel well, but I think my wife would say I complain a lot about them haha. I'll reconsider and pare down if possible. This might have been the most helpful post for me to truly see. I don't know if we will be able to or not.

Allset2travel mind sharing your personal reasons for those three ? I believe Japan, Egypt and Italy will be my favorites eventually but that is just a guess. I like the idea of China but don't know enough of their history currently. I'm a little weak on Asian countries history.

Would a better trip be to Cairo for the Pyramids if I'm look for historical stuff? Italy and Pyramids are my top two must see with Japan's Cherry blossom and Tokyo close behind..

Thanks for all the help guys! Loving this conversation, it is very helpful.

Well, about my personal preference for visiting Japan, Italy and China, not sure where to start.
First Japan: Love the culture, my wife and I both love their food (all kinds), and I am a travel photographer (Japan has plenty to shoot). Japan is the safest place to travel, IMHO. On top of that I had spent a few years working for a Japanese multi-national in hi-tech. Still have many friends in and around Tokyo. Cherry blossom and fall foliage are 2 best seasons to be in Japan. On the subject of Japanese Hanami, I had posted a trip report on FT:

https://www.flyertalk.com/forum/trip...=#post24795822

Below are images from various places in Japan, see what inspires you.
https://stefanofoto.smugmug.com/Asia-AU-NZ/Japan

Re Italy: Love the history, arts and culture; Museums and churches are tops. I spent many trips to Rome. Country side is amazing: such as Umbria, Tuscany, Amalfi Coast, Cinque Terre and many small towns in northern Italy, not to mention Lago Bellagio & Como. Love the Italian food from all regions. I feel at home in Italy.

About China: I didn't start going to China until 2008. I was on a mission trip to serve in south west region of China. I am hooked ever since. Been back a lot except during the pandemic. The country is vast and diverse. Love the train system which makes traversing the country so easy (without the airport hassle). China has a lot of photo-ops in terms of landscape and city-scape. The food is amazing by region. Has the longest history that spans 6,000 years. Many sections of the Great Wall one can climb.

Egypt: I had tried a number of times to go to Egypt in vain. Reasons varied, personal safety being one. I came as close as having a RTW DONE4 booked ex-CAI. First flight would have been on QR. But QR canceled way before my trip began, for political reasons. Oh well. For history buff, Egypt is a must. I hope I’ll make it there one day soon.

OK, enough about all that. Let's return to your itinerary. These are just suggestions with an emphasis on logistics (since we really know so little about your preferences).

Day Onein Milan: From MXP, take the airport shuttle bus (recall Autostradale?) to Stazione Centrale. Stay in a hotel near the station for the night. Recall a Hilton nearby among many non-brands. Drop off luggage and do the town. Please note Central Station may look a bit creepy at night, so just be careful of personal items.

Train to Venice: 3 to 4 nights in Venice(depends on your interest), 2 days to see Venice itself maybe enough. Murano Island requires half day. Use extra day(s) to plan day trip to some smaller towns in the Veneto Region.
In Venice, pick a hotel near the Venice Station if possible for convenience, but not a big deal. Note most narrow alleys (streets) are paved with cobblestones and tough on rollers. Of course water taxi (gondola) is available.

Train to Florence (avoid taking the train mid-day for obvious reason). Stay 4 nights to include some day trips (lots of candidates but depends on your interest: Lucca, Pisa, Siena). If you do only one, I’d do Siena. Allow 2 days for Florence itself.

Train to Rome. Stay here for the BALANCE of your days (yes, sorry to suggest you drop Pompei because of logistics). Book a hotel near a Metro Station or a Local Train Station (very important). Rome will get you busy every day. Make sure you have good walking shoes. Day trips are possible. Hope you like history, architecture, museums, Vatican, markets, gardens and food etc…

To do Pompei and the Amalfi Coast, a rental car would better serve the purpose (pick up & return FCO ). Otherwise you have to book private transportation (public transportation available but plenty of hassle for a first timer to Italy). You can join tours once you settle down in a hotel. If you indeed go to Amalfi, Ravello would be my choice as base.

Push comes to shove, you can do Pompei & Mt Vesuvius Tour from Rome. May cost about $160 per pax and a long day. Hey, you don’t need to carry luggage and can catch up on sleep while on the bus! I am sure you can check it out online.

I had a car when I did the Amalfi. I based in the south, a town named Salerno (not only cheaper for hotels, but it had big city amenities, think restaurants). Seafood and pasta were marvelous!

Did you detect a common theme above: FOOD! Yes, food is part of the culture in any culture.

Hope you are having fun in planning your trip!

OP - you may wish to reconsider this idea of not traveling with children. We have four and took them all over the place. Many countries (Italy is a prime example) are welcoming to families with children. And your kids will appreciate the memories you give them, and will hopefully become more interesting and inquisitive people in the process.