14 day Italy trip

Based upon what you've written, you're gonna spend more time driving, searching for the correct off/on exit, and seeking parking while avoiding ZTL zones, then actually enjoying your trip. It can be done...but, it won't feel like a vacation but an endurance march instead.

Before advice can be provided...where are you flying into and out of?

Car is bad for visiting cities, good for small scenic villages, scenic drives, and countryside. .

Participating in the Mille Migli, would be a a more relaxed tour of Italy.

Given the geographic spread of your destinations and the choices themselves, a record or near record number of ZTL violations and speeding tickets is the most likely result of attempting this trip.

Enjoying a vacation in Italy does not seem to be on the agenda..

Sorry about the bucket of ice water, but what you contemplate is so impractical, I would need to resurrect my thesaurus to find adequate words.

You really need to prioritize what you want to see and map it out to see what is practical.

Have you done a similar trip in Europe before? I ask because this sounds like a miserable trip to me. You are going to cities, not villages. That means city driving and the dreaded ZTL's. Few hotels in historic centers (where you want to spend your time) have parking facilities, so you either have to park near the center (expensive!!) or end up commuting into the center (wasting time).

So yes, we are staying in B&B's outside of city centers. All of our places are about 15-20 min by metro or bus and these are within walking distance. I did this in England and Scotland and it worked great due to knowledgeable hosts at B&Bs. All have free parking at site. A couple are agriturismo. We are flying round trip to Milan and our longest drive will be from Rome to Milan on the 12th day with a stop in Bologna. There is no rush that day cuz we are staying night in Milan and catching plane in morning.The earlier trips are no more than 2hr drives and we are early risers so not problem. I was hoping for some advice on the stops and not expecting so much negatives but again I am not experienced in Italy. We like being able to stop any time and not worrying about time tables, stops, missing trains, getting tickets stamped etc. We just did Ireland this way as well. My husband drove about 1100 miles for 12 days and we saw a little of the whole island. It was beautiful.

As long as you know what you are getting into it could be done. It's just a lot of seat time in a car in a very short amount of time. You'll be able to check the places off your list (we were there) but you won't have much time to really see anything. For perspective, my wife and I were in Italy last May for 21 days and we went to Venice, Florence, Cinque Terre, Orvieto and Rome. We rented a car only in Orvieto and used it while we stayed in a nearby Agriturismo and to explore Tuscany and Umbria.
Driving was not a particular challenge for us but many folks have horror stories and lot's of expensive fines and tickets from their experience. We avoided these because we did not drive in Rome, Florence, Venice, Cinque Terre.... using the mix of available public transportation and the car was (IMHO) the only way to do this. It's not the UK! I have rented a car in the UK and driven all over through Wales, Scotland etc...and it is not the same. You really should give the trip plan (length, driving and locations a bit more thought out unless you really are locked in on checking the boxes.
2 nights in Rome, I wouldn't bother, and Milano, why? The Last Supper..? You will never forget driving there...that is where I learned how Italians truly pronounce certain profanities...from a cab driver....it was on par with a cab ride in China 30 years ago but at three X the speeds. They drive on the trolley tracks to pass...when there is a trolley coming at you on the track!
My wife and I decided that Italy needs time to explore it properly so we decided to leave Pompeii and the South regions for a future trip...and Rome needs at least three days...and my wife wished we had another few nights in Venice...
You really should reconsider your plan.....but yes, it could be done..

Make sure you are up on all driving requirements, parking (ZTL) and speed limitations - no grace period or 5 miles over the speed limit. Plenty of posts here telling about tickets received months after incident with all the related penalties attached.
If you know what you are getting into, it could be a lovely trip. Very scenic.

Just so you're up to date on driving in Italy, please read this and download their e book.

https://www.italybeyondtheobvious.com/dont-mess-with-ztl-zones

It has good info on signage, speed cams, and rules of the road. I've driven in several European countries, and Italy has some unique ways of getting an expensive ticket. Be sure to get an IDP, traveling without one can result in a very high fine.

Most of your driving is between cities on the autostrada, not much more to see than any road in the states. You'd need to make a concerted effort for a lovely drive with beautiful views/towns. To do so means traveling on back roads with the SR/SP designations. Which would mean your expected 2 hours between locals could be 3-4 hours.
The best planner for Europe is Via Michelin.com.
Even then plan on adding 10-15% time wise.

I, personally would skip Venice and Pompeii,
Adding those nights to Florence and Rome.

To simplify your trip do this.

On arrival, train to Florence 4 nights nights
Day trips to Bologna under 40 minutes by train, and to Verona.

Rent car, 2-3 nights Tuscany.
This is where you'll have beautiful vistas and hill tip towns.

Tuscany-Rome 3 nights. Drop car Roma Tiburtina. Taxi 10 min to lodging.

Train Rome to Milan 1-2 nights.

Your best bet would be to take the train through Milan, Verona, Venice and Florence.

Once in Florence, rent a car and visit the various towns around Tuscany (Siena, San Gimignano, Lucca, Voltera, etc..)

If you absolutely must visit Rome, take the train from Florence and spend 3-nts there. Return back to Milan via train, spend another night and fly out. Skip Pompeii and the rest of the Amalfi and Sicily for a separate visit.

Italy is a bigger area than the UK, however it's got a lot of length, so the distances are greater, not to mention the ZTL-zones are financial crushers if you cross into...which many, many have. You really need to evaluate the amount of time spent in-transit versus actually visiting and how you're going to enjoy these destinations; are you simply box-checking? If this is your first time visiting Italy, and you've already purchased your flights, you should likely just stick with the four cities: Milan, Venice, Florence and Rome, spending 2-3 nights in each with some margin built-in.

So originally we were going to stick with Northern Italy and not do Rome or Pompeii but I have 2 teenage daughters one who is graduating and the other turning 16. This is the reason for trip. And we all win. No huge parties etc. lol Their two big things were Rome and Pompeii but I had already booked round trip tickets to Milan(great price)! Couldnt pass it up. I know we will not see everything and probably my husband and I will make it back one day. If my husband can handle Ireland roads, which most credit card companies wont even cover, I think he will be fine driving. My question originally was Tivoli or Orvieto. I appreciate all the advice. We live in Florida where nothing is close and no trains or buses(that are convenient) Everything is far. Miami is 4 hrs from us and we have made that trip a lot. I appreciate the advice and I might drop car off in Rome and train back to Milan. I find the responses interesting when there are so many tours that do 3-4 countries in one week. I feel like that is more stressful? How can you see everything that way? It seems so rushed? We are on a budget and seeing every museum and church and tower is nearly impossible for 4 people. We are doing the best of best if possible. But maybe I am naive.

I find the responses interesting when there are so many tours that do 3-4 countries in one week. I feel like that is more stressful? How can you see everything that way? It seems so rushed?<<

You can't see everything that way and most here do not travel that way. I think a lot of us consider RS tours itineraries to be way too fast paced.

2 nights = 1 day to sightsee- and a half day to get there, get checked in, get acclimated, find your way around etc. Staying even 15 min outside historic centers really means about an hour getting to and from your lodgings to where the sights of interest are.

In general most here would suggest 4-5 locations MAX on a 14 day trip. Nobody wants to spend all their time in a car on the highway where scenery is dull and actually quite ugly.

I'll echo Gerri and say be sure all drivers have their IDP, that you are familiar with ZTLs, speed cameras, traffic patterns, parking restrictions, etc.
and make sure you get a car big enough for 4 people plus their luggage and that luggage should be hidden if you intend to stop along the way leaving luggage in the car.

Which cities do you think require more than 2 nights? And maybe I could tone down the itinerary. Do you think breaking up drive with one night stay between Florence and Pompeii is bad idea? I really cant give up those two cities. Life is short and who knows, I may never be back. I guess we tend to go big and go hard cuz the world is so big and so many places to see.

Ok, to address your original question, Tivoli or Orvieto. I have been to Orvieto, but not Tivoli. Orvieto was truly enjoyable and picturesque. I suspect there is no 'wrong' choice.

If your plan was to drive from Tivoli/Orvieto to Pompeii , see the site and stay a night before heading back north, then Tivoli gets my vote, just because it means less driving that day and lets you get an earlier start to see the Pompeii site.

If the trip is a graduation gift for your daughter who's wish list is Rome and Pompeii, I think you need to cull your destinations to a smaller number to make a more manageable trip.

Having Milan as your entry/exit point is far from ideal given the choice of Rome and Pompeii as the prime wished for destinations.

Just what order are you planning to do. the trip? I am curious where the one night in Venice fits.

We fly into Milan and stay for 2 nights than go to Lake Hard on way to Verona for 2 nights. Verona to Venice one night. Then Venice to Florence.

Sorry Garda.

2 nights = 1 day to sightsee- and a half day to get there, get checked
in, get acclimated, find your way around etc. Staying even 15 min
outside historic centers really means about an hour getting to and
from your lodgings to where the sights of interest are.

I'll echo this concern as that one full day you might have might be the 1 day the attractions you wish to see are closed or it pours rain. IMHO, 6 locations in 14 days (and if you're counting arrival and departure days it's not really 14 sightseeing days) is about 2-3 locations too many. And I'd ditch the car unless using Gerri's plan.

I find the responses interesting when there are so many tours that do
3-4 countries in one week

Tours are different: they line everything up FOR you so you're not having to find the hotel, find the parking, find the train stations, find your way from A to B... Transport (bus/van) is usually waiting for you right outside the hotel entrance to take you directly to the next stop or attraction. And frankly, too many escorted tours are hit-and-run marathons of those attractions: get off the bus, take the picture, hustle along... You can SEE a place or you can EXPERIENCE one. There's a difference.

Even loyal devotees of RS tours counsel against using those itineraries as a guide for independent trips due to arranged transport and escorted assistance.

We're really not trying to gang up on you, just trying to make this a more memorable trip.

Here's another option...

On arrival MXP, fly to Naples NAP. Meridian Air has a flight at 12:30. Cost is $55.69. 1hr 30 min.
(I picked a random flight in June)

2-3 nights. Either stay in Naples, or take the Curreri Viaggi bus to Sorrento. 1H30m €10 p/p.
This allows you time to get over jet lag and a full day for Pompeii. Then a straight line course back to Milan.

Naples-Rome. Train 1H17m

3 nights Rome.

Rome-Tuscany. Rent car. 2H50m. Stops along the way. Orvieto, Montepulciano, Siena.
2-3 nights Tuscany.

Tuscany-Florence 1 hour. Drop car.
3 nights Florence. Visit Bologna from here.

Florence-Verona. Train 1H30m
1 night Verona.

Verona-Milan. 1 night.

Just an FIY,most credit cards do not cover insurance in Italy. Check to be sure.

I've been to both Tivoli and Orvieto. With a trip from Rome, Orvieto would be my choice.

But I adore Tivoli, especially Villa d'Este.

https://www.gardenvisit.com/gardens/villa_deste

Thanks. I am gping to get with my friends who also will be traveling with us and revamp it. We leave last week of May so hopefully I will have ot together by then. Maybe I will have some tips of my own when I get back.

Driving in Ireland vs driving in Italy- there is no comparison. We’ve done both. Ireland was a breeze, Italy not so much- and we ONLY drove in the Tuscany region, would not have dared driving into or near any big cities.

I think you need to make a short list of what your top priorities are. Once you have determined those, add in the “would like to see”

How many NIGHTs do you actually have?
Are any of the lodgings booked non-refundable?
When is this trip?
Your flight is set in/out of Milan- so if we have a better idea of what is really important we can probably help you fine tune this trip and make it as enjoyable as possible.

Have you done a cost analysis of driving vs train? Gas is $5-6 a gallon, how much will your tolls be? parking ? how many tickets will surprise you in mailbox months or even up til a year after you are home? Do a search on this forum for speeding tickets/ZTL tickets in Italy and you’ll understand.

Train travel in Italy is so easy, fairy inexpensive, quite comfortable, very fun, stress free and quick.
I like to use
www.rome2rio.com to see what options there are- how long trains take, expected price etc. It's a very good starting point
www.viamichelin.com can help you with gas and toll costs.

You have mentioned Rome and Pompeii as priority

Milan- the only thing there I’d consider important is The Last Supper- needs to be booked well in advance- if trip is soon, you are probably out of luck.

Venice needs a MINIMUM 2 nights- 3 is better. Especially if you are staying outside Venice proper which you must be since you have a car. Coming from the outlying area you will spend half your day just coming and going. Venice is crowded and honestly I am not even sure how far away you’d have to park. We loved Venice, are going back next month- did 3 nights first trip, this trip just 2 and I could kick myself for cutting it that sort.

Florence- 2 nights MINIMUM, 3 is better. If you don’t care about the art then 2 is fine. But with 2 nights IN Florence you can add 2-3 nights in Tuscany. I wouldn’t dare drive anywhere near Florence- we picked up our car outside the city and drove away.

Orvieto- have not been - we just couldn’t fit it in last time and I regret that- we will visit when we go back to Tuscany area. I think 1 is fine there. Car rental agencies are right at train station so this could be an option for pick up/drop off rental.

Rome needs 3 nights MINIMUM, and that doesn’t even scratch the surface. I’d do no less than 4.

Pompeii- most visit from Naples or Sorrento-very easy on the train- it’s a bit too far for day trip from Rome and I would not want to drive from Rome to Pompeii.

A typical first trip to Italy is the 3 major cities- Venice- Florence-Rome. Then chose either time in Tuscany or time in Amalfi.
Verona, Bologna, Orvieto etc are all sort of secondary priorities for first timers.

Assuming you have 13 nights:
Arrive Milan- take 2 hr train right to Venice-3 nights.
2 hr Train to Florence- 2 nights
Pick up rental car- 3 nights in Tuscany- we loved Montepulciano & Pienza- I think Montepulciano has a “Twilight” connection- are your daughters into that or were they? Volterra does as well
Drop car- not sure where? maybe back to Florence- then train to Pompeii if you must STAY there.
I would just go to Rome (you will need to go thru Rome anyway) and stay the next 5 nights.
3 hr Train to Milan for 1 night before departure.

There are day trip tours to Pompeii from Rome- it is a long day for sure but can work.

Italy is not just churches, towers and museums. I’d guess your daughters would enjoy the markets, the piazzas, people watching, exploring hill towns in Tuscany, eating, riding vaporettos in Venice, etc.

Using a combination of trains and rental car with more train than car will likely give you a cheaper trip and more time to enjoy the experience.

The other thing about trains is you can depend on the time it takes. If train says 2 hours- it is 2 hours- unless delays/strikes, etc- but when Google Maps says 3 hour drive that can very easily turn into a 5 hour drive.

Also gotta be honest the thought of spending that much time driving in the heat and crazy traffic with 2 teenaged girls in backseat might send me over the edge. LOL Although I guess there is always a bottle of wine waiting at next stop. I would need that.

I like Gerri's last plan very much.

I am gping to get with my friends who also will be traveling with us and revamp it.

Aha, ....planning by committee and trying to mesh TWO wish lists into one itinerary adds insight to the origins of ambitious original plan.

As gerri said, no one is trying to beat up on you, but hoping to help you create a manageable and enjoyable trip for the time you have.

Trying to drink out of a fire hose usually is not the best way to satisfy one's thirst.

Joes' analogies are cracking me up.

Oh more people traveling?
Then you’ll need a very large car!
Or get 2 cars but trying to travel following each other “caravan” style could really be a nightmare

We’ve always used www.autoeurope.com for our European rentals
They are a US based consolidator and can usually get you the best price
They are extremely helpful and knowledgeable,

You can check out your rental locations, options and prices on their website.

Also keep in mind, most rental agencies are closed on Sunday and open only half a day on Saturday if at all

To add, using the last itinerary, Florence-Verona, you could check your luggage in Verona.

http://www.grandistazioni.it/cms/v/index.jsp?vgnextoid=f6206dab180eb110VgnVCM1000003f16f90aRCRD

Then take an evening train to Milan. This would eleminate the awkward 1 night stay.

Leaving 2 nites in Milan.

Christine's recommend Auto Europe is one we've also used. I usually utilize either Europcar or Hertz.

On sundays, all airport locations are open for business.

Did your children go with you to Ireland? It is different traveling with larger party and every thing takes more time. If this the pace you are all used to, then go for it.

My husband and I were in Amalfi Coast for 10 nights a couple years ago. All one or two night stays. We were exhausted and ready to go home by the end. Last year we went to Greece for 14 nights with our adult children and husband’s brother. There were 7 of us. We stayed in four places. I knew I could not repeat the pace we had in Italy with larger group for a longer time. We found that to be a good pace for our group.

Every body is different but make sure you are taking into account different composition of travelers and different country. We found out quickly, for example, that trying to generalize from our experiences in Italy and Austria to Greece did not work. Same for you from Ireland to Italy. We are going to UK this year and are having to learn some things all over again.

And can everyone fit in one car? We could not and we have a few stories of mishaps-like when I thought I was following my husband and it was another white car.... I had gotten stuck behind someone very slow paying tolls and had lost him. Greece does not have a good train system so there were not a lot of options. Italy does have a good train system.

I'm sure your family will forgive you eventually. ; )

Seriously, this sounds too much like National Lampoon's European Vacation

Yes my kids were with us. There we had 12 days in March. We did Dublin( stayed in Rush), Bushmill, Donegal, Doolin, Dingle, Killarney and part of Ring of Kerry, Rock of Cashel, and back to Dublin to fly out. We did 14 days in England and Scotland and had a blast 2 years ago. Same deal 2-3 nights everywhere. London, Bathe, York, Glasgow, Edinburgh, back to London. York and London were our favorite!

OK--- You have found a pace of travel that suits you. As you can tell ,many here find it too hectic. I wish you well.

Have your friends traveled with you before and are accustomed to your pace?

No but I am laid it on the line for them. That is why we have 2 cars. We are not the type to have to do everything together so as long as we share breakfast and dinner together, we are good. It is their experience too and we aren't holding them down to anything. We are staying in same B&B's and only one apartment together. 2 of the stays, they are down the street. But they are very easy going people so I am pretty sure they will follow my lead.

Joes' analogies are cracking me up.

My side hurt!!! Joe wins for best laugh today! 🤣

No, we really don't mean to be ganging up on you, amknight73, We just want you to have a FABULOUS trip, thus the poking at some potential pitfalls. 🙂

Sounds like you are comfortable with your pace and style of travel. And if you’ve done this in UK, Ireland you are certainly aware of the daily logistics—checking in/finding your way/checking out/moving along.

Please do heed the advice about auto rental and driving in Italy.
Learn a few phrases in Italian.

Your daughters are lucky they have seen so much of the world already.
You’ve done them a great treat- now they’ve got the rest of their lives to “travel often, travel widely” as my father taught me.
It’s a good bet you will all want to go back to Italy at some point in time for a more focused trip.

Congratulations to your graduate and happy 16th to your younger daughter!

Thanks! I will pass on the message! I leave everything in the Lord's hands and do a lot of praying on trips. My hierarchy in life is God, family, travel, food. Those last two are interchangeable. Lol. But I cant say I have ever had a "bad" trip or wished it would have been different. We have just taken notes along the way for others. This family always has a story when we come back. :) We just love seeing different cultures, meeting people, eating the food, etc. We have met some great people on our trips! That is why we have so many diverse friends. They like to invite us over to eat because we eat everything. :) We are bringing a Jamaican/Puerto Rican couple with us who have never been to Europe. So for them, I might refocus and scale back a little. Maybe take out Verona. We like to do outdoorsy stuff too and I thought staying in that area and seeing Lake Garda would break it up a little with enjoying countryside and nature.

Before you depart, listen to that Savoy Brown/Foghat classic, Hellbound Train a few times. You should have that tune in your heads as you go whizzing around Italy. No one has mentioned this yet, but consider...a car that comfortably seats four with luggage is too big to fit on many of the streets that you will end up trying to drive on...oh baby. Nothing good can come from this.
Driving in the UK is not the same...
You are getting a lot of suggestions to pare down your plans and they are not sinking in. What might be fun is if you proceed as per your plan and then come back to the thread after your trip and share how it went. We (experienced travellers) might have it all wrong...please share on your return.

Take the train whenever possible; at least it will be more tolerable for your children. Especially the Florence to Naples (Pompeii portion).

Drop Milan. Make Venice two nights and if your really want to, do a day trip into Verona (but I would just enjoy my limited time in Venice).

Frankly, you sound very unprepared. Read more travel reports. Learn to use public transport in Italy. The car is not your friend there. Time to open your mind to other mode of transportation.

Personally, I think you and your family will be fine from what you have said-although it is too fast paced for my tastes. But I do wonder about your friends. Are you thinking that one of them will drive a different car? That might be a lot to expect of a new traveler to Europe, especially with that much driving. Personally, we avoided driving in Europe taking trains and buses until we went to Greece last year. My husband and I both drove since we had 7 people. It was the best choice for us in Greece but I did find it exhausting and we did not move that much and it was mostly day trips.