Rethinking a busy schedule - suggestions?
 

I asked last week for some advice and have rethought our itenerary thanks to so much good advice. I'd like some insight as to if this is a realistic trip. My desire is to have a rental car for most of the trip, probably excluding only Venice.

Day 1-2 - Fly into Naples ... Naples to Amalfi Coast
Day 2-6 - Amalfi Coast
Day 6-8 - Tuscany Region (Agrotourismo?)
Day 8-10 - Venice
Day 10-11 - Dolomites
Day 11-14 - Lake Como
Day 14-15 - Milan
Day 15 - Fly out of Milan

I know depending on flight times, etc. this will need to be tweaked, but it's a pretty good starting point for what I (in my mind) think would be a fabulous vacation. We are hoping to do sometime late September to mid-October, although I realize we are late getting started planning for those times and might run into some booking issues.

Thanks again for any input!

Craig, IMO this is too much, too quick. You are planning on seeing 4/5 different provinces in 2 weeks - 3/4 days per province. Given the regional variety in Italy (food, people, sights, culture etc), IMO this is too much moving around and hopping between places.

If you are restricted on the flights in and out, then at least cut Venice and Lake Como. After Tuscany, then why not spend a few nights in Cinque Terre before going up to Milan.

With what you propose you are a bit all over the map and may find the travel a bit much and that it takes up an undue proportion of your trip.

If you look at your schedule you have yourself in two different places on the same day (days 6, 8, 10, etc.) For instance, on day 8 you can't be both in Tuscany and in Venice. Well...I guess you could but it would not be a full day in each place.

I don't think agritourismos rent for only 1 night.

Too much time on the AC as the weather can get damp and rainy in late September. What are you going to do there for 5 days?

Do you have alternate plans in case it rains? You've booked mostly an outdoor vacation late in the season. Many towns on Lake Como begin to shut down October 1.

I just looked at your other thread and see that you are planning a romantic trip. Does your other half believe this is romantic? Have you consulted her/him? Other than Venice I don't see any romance to this trip.

I prefer to show itineraries as adrienne implies--in such a way that you can see how many full days you really have in a place. After a leisurely say on the Amalfi Coast, your plan includes a lot of driving and changing locations. Have you estimated drive times between the various locations?

Day 1- Fly into Naples ... Naples to Amalfi Coast
Day 2 - Amalfi Coast
Day 3 - Amalfi Coast
Day 4 - Amalfi Coast
Day 5 - Amalfi Coast
Day 6 - travel to Tuscany Region (Agrotourismo?)
Day 7 - Tuscany Region (Agrotourismo?)
Day 8 - travel to Venice
Day 9 - Venice
Day 10 - travel to Dolomites
Day 11 - travel to Lake Como
Day 12 -Lake Como
Day 13 - Lake Como
Day 14 - travel to Milan
Day 15 - Fly out of Milan

You've got Amalfi town (4) Tuscany (1) Venice (1) Lake Como (2) and no full days anywhere else. It's possible but sounds rushed. It sounds as though you are just driving through the Dolomites to get to Lake Como but not stopping enroute. What will you do with the car while you're in Venice?

Is it possible to fly home from Venice? In which case you could visit Amalfi (day 1-6) Tuscany (day 6-9) Lake Como (day 9-12) Venice (day 12-15)? That would give you full days in Amalfi (4) Tuscany (2) Lake Como (2) Venice (2). Consider carefully whether you need a car.

We've been in that part of the world in September/October a few of times and found the weather to be beautiful, although of course there are no guarantees - better than when it's too hot.

"After a leisurely sTay on the Amalfi Coast . . ."

Too much.

It looks like your "day one" is really the day you leave for Italy, and if day 15 is the day you leave for home you really only have 13 days time on the ground.

Save the Dolomites for another time. One less day on the Amalfi Coast. Staying in Milan the night before you head to the airport isn't bringing you much closer to the airport than if you had just stayed on Lake Como. There is no comparison Milan/Lake Como (especially with only part of one day), so stay on Lake Como. If you must, the last night in Cernobbio which at least means 30+ minutes less travel time to the airport from mid-lake.

Consider:

Day 1- Fly into Naples ... Naples to Amalfi Coast
Day 2 - Amalfi Coast
Day 3 - Amalfi Coast
Day 4 - Amalfi Coast
Day 5 - travel to Tuscany Region (Agrotourismo?)
Day 6 - Tuscany Region
Day 7 - Tuscany Region
Day 8 - Tuscany Region
Day 9 - travel to Venice
Day 9 - Venice
Day 10 - Venice
Day 11 - travel to Lake Como
Day 12 -Lake Como
Day 13 - Lake Como
Day 14 - Fly out of Milan

The above is still somewhat rushed so consider dumping yet one other region and spreading those days among the time remaining.

I think the latest itinerary suggestion is a bit more reasonable but I disagree with all this "rushed" complaint stuff.

There is no way anybody can know if you are "rushing" because you have not said what you are planning to DO.

For example, the days on Lake Como. If you want to get on every ferry and visit every possible place then yes, i'd say it is a bit rished. OTOH if you simply want to do what a lot of people do at the lake, take it easy, veg out a bit, perhaps take a couple of shorter day trips, then no, it is not "rushed."

Venice: you can see the major sites in Venice in two days but the problem is there are a lot of "major" sites in Venice depending on your interests.

I agree with skipping Milan and I also agree with not even trying to get into the Dolomites between Venice and Lake Como.

Is there some reason you feel you have to have a car for all these segments? I suppose some might say you need maximum flexibility but if there's anything that PROMOTES a rushed itinerary it's having a car.

Flygirl has the best answer.
That is a fabulous itinerary. Any more would be too much.

Thank you so much for all the replies and suggestions, there is so much good advice. I agree that Flygirl's itinerary sounds very attractive. The major sights in Venice are not a deal breaker for us, we probably can leave happy with 'just a taste'. We both would rather the Amalfi Coast and Tuscany regions. Thanks for the suggestion about not staying a night in Milan. We had no other reason to stay there except for flying out, so it does give us that extra night for Como.

Here is my tweak to throw in a couple items high on my list:

Day 1- Fly into Naples ... Naples to Amalfi Coast
Day 2 - Amalfi Coast
Day 3 - Amalfi Coast
Day 4 - Amalfi Coast
Day 5 - travel to Tuscany Region (Agrotourismo?)
Day 6 - Tuscany Region
Day 7 - Tuscany Region
Day 8 - travel to Venice
Day 9 - Venice
Day 9 - Venice
Day 10 - travel to Ortisei (via Cortina)
Day 11 - travel to Lake Como (via Stelvio Pass)
Day 12 - Lake Como
Day 13 -Lake Como
Day 14 - Lake Como
Day 15 - Fly out of Milan

I know the travel seems to take up much of our time, which we are a little torn on ... but we both very much enjoy driving and seeing out of the way places and backroads.


adrienne: Romance is in the eye of the beholder and my wife and I very much enjoy the same things and will find 'romance' in many places throughout this vacation. I know there is a wide variety of locations & culture but that is part of the plan. With 3 young children I don't think we'll be back anytime soon, so we want to experience as much as possible.

Thanks again to everyone taking the time to give us advice, it is much appreciated.

I can see where a rental car in Amalfi & Venice would not be needed. Would it make sense to just rent a car & return it in Tuscany, then rent another when leaving Venice?

I would reverse this trip since you plan to travel in Oct. You will find the weather in the north starting to get quite cool and rainy. I would put the north first for that reason and end on the Amalfi coast.

Our hope is to Leave around Sept. 21 and return Oct. 6 but it may have to be adjusted if we run into issues getting places we like on those dates. Reversing it is certainly an option although I have seen many reviews that early October can be quite lovely in the north ... but with weather you never know.

...but we both very much enjoy driving and backroads...

Having just returned from a 4000k 3 wk Italian driving trip
I would like to point out that a lot of autostrada driving
is most certainly NOT enjoyable - the trucks, the trucks!

Also, taking the 'blue' roads certainly takes you to small
out of the way towns but it does take a lot more time to
negotiate all the round-abouts and heavy local traffic.

Road trips take a lot more time than the maps would indicate.

JMHO after many an asphalt adventure...

Firstly, I do not think you would have booking issues (I would not know about flights from your country) as the season you are going is not the peak tourist season.

I would recommend that you start off and take flight to Venice, as you would not need a car in that city for sure, waste of money, plus as another reviewer said, leave the warmest region till end of holiday. Plus I often read on Fodors that flights from Venice back to the US leave really early in the morning, another reason to start off your holiday from Venice, and depart back to USA from Naples.

You might also find driving near Naples and Positano and around Amalfi coast also a bit challenging. So I would drop off car when reaching Naples before starting your visit at Amalfi Coast.

Como is only about an hour's drive from Milan, so if you really want to visit the city (not at all a favourite of mine) you can do a day trip from Como - so skip Milan.

So, keeping in mind your preferred places of interest and inclinations, I would plan stops as follows (I prefer to use nights because of accomodation) - I am assuming that since you have 15 days available, then it is 14 nights at your disposal:

Fly to Venice

2 nights Venice

Hire car and head to Ortisei (about 3 and a half hours' drive)

2 nights Ortisei (no point staying just one night after a such along travel and also considering that you cannot be sure what the weather would be like, plus the majestic dolomites are breathtaking in that area)

3 nights Lake Como

3 nights Tuscany -(check Agriturismo Nicolai Palagetto di Sotto - lovely agriturismo just outide the city walls of San Gimignano, yet still in the surrounding beautiful countryside, they also produce their own wines and olive oil)

Drive (without stopping to visit any towns on the way) to Amalfi Coast and drop off hired car, maybe in Naples and take train to Sorrento.

4 nights Amalfi Coast (I suggest 4 nights here, as it would take a whole day to drive to Naples and then train to Sorrento, so at least you would have 3 full days to visit this area.

Fly back home from Naples

I tried to stick to your desired itinerary, and tried to give you a bit of rest in between travels, but bear in mind that you would be covering five regions of Italy, and would be travelling from north to south. But at least apart from Venice to Treviso to Como, where you would be travelling towards west, your other travels will all be in the southern direction. Again, if you do not mind the driving, go ahead, but be prepared to do lots of it. Having said that, driving in northern Italy (given that it would be nice weather) is such a unique experience, so very beautiful, you would not see the time passing and be wishing that the drive never ends.

Another reason to consider north first is that you want to cover some passes. The Stelvio will probably be open, but, it will be a lot colder at the top and any precipitation would make it a not-fun ride. Will almost two weeks earlier make a difference, temperature-wise? I don't know, but it makes sense that it may.

First of all, thank you to everyone for the tips & suggestions ... it is really helping us to start to piece together our trip.

My dates have changed due to a work conflict for my wife, so unfotunately I can't follow Anna's itinerary in the order she suggested (thank you Anna, it sounded really good to me) due to the flights that we now have booked.

We will be starting our vacation on Friday, September 28th flying out of Oklahoma City via Dallas/London arriving on Sat. the 29th in Rome. Our flight home will be leaving from Venice on Sunday, October 14th via Madrid/Chicago to OKC. That will give us 15 nights in Italy.

Day 1 - Sat. Arrive & stay in Rome
Day 2 - Sun. Rome to Amalfi Coast with stop to see Pompei
Day 3 - Mon. Amalfi Coast
Day 4 - Tues. Amalfi Coast (Capri)
Day 5 - Wed. Amalfi Coast
Day 6 - Thurs. Travel to & stay in Tuscany Region (Car rental)
Day 7 - Fri. Tuscany Region
Day 8 - Sat. Tuscany Region
Day 9 - Sun. Travel from Tuscany to Lake Como
Day 10 - Mon. Lake Como
Day 11 - Tues. Lake Como
Day 12 - Wed. Travel from Lake Como to Ortisei
Day 13 - Thurs. Travel from Ortisei to Venice (Return rental car)
Day 14 - Fri. Venice
Day 15 - Sat. Venice
Day 16 - Sun. Fly Home

I will say that the Lake Como part of the trip is the part most unsure for me. After reading replies it seems like I should consider dropping this region. We don't have a huge draw to Venice so we might split the days saved from that between an extra night in Rome & maybe an overnight trip from Venice to the Dolomites(?).

I feel like I am getting close ...

My very first thought on your last itinerary is that stopping to see Pompeii on your arrival day might be exhausting. It's a BIG site. However, if you keep up with 3 little ones, maybe you can do it!

On my last trip, I traveled down to Praiano on arrival day and was really beat by the end of the day. I also have spent about 7 hours total at Pompeii over two different trips as it was a major priority for me.

I would just say you should consider a few variables before planning to visit Pompeii on day 1 in Italy - such as are you able to sleep well on long flights? How much does jet lag affect you? How much interest do you have in seeing Pompeii? Would a 2 hour visit seeing the highlights be "enough", or would you want to spend more time?

The Dolomites are spectacular! I like your itinerary above. You might consider skipping Capri. Personally, I like the Amalfi Coast just as much and thought Capri a little overrated.

Hope you have good weather to enjoy all these gorgeous places.
Buon viaggio!

I think your trip now sounds much better. It's a personal choice as to whether or not you drop Lake Como so I'd go to your local library and get some photographic books or look at photos online to see whether you prefer that or the Dolomites.

If you are only overnighting in Rome to rest, then I recommend you stay near the main Rome train station (Termini). It's not Rome's best area but it's not too bad either and it won't be worth lugging your stuff further afield. Rome central area is actually very walkable and you have easy access to the metro and buses from Termini as well.

I wouldn't overly worry about being tired the day after you arrive as you'll be excited and looking forward to your holiday. I travel 25-30 hours to get to Europe and I'm always ready to get going the day after arrival (I crash when I get home!).

Craig, you have a packed schedule. I would advise you not to go to all of the places that you have on your list. Don't bring a lot of luggage. One cannot rush through Italy. You need to take in everything that you see. Italy is to be savored. Promise yourself that one day you will return. I have been in may and October. October was the best for me. I hope you have a wonderful time and bring back many happy memories.

Lake Como is lovely, try not to skip it, since you are travelling by car, therefore no train/bus hassles. It looks like a really good itinerary, bearing in mind that you have a lot driving to do, but still you are going to see some beautiful scenary on the way, so you will still enjoy it.

I would just change one thing. I would do 2 nights on Lake Como (instead of 3) and 2 nights in Ortisei. That area of the Dolomites is really really spectacular (we visited Madonna di Campiglio last December, but Ortisei, which we visited in 2005, in my opinion has more spectacular mountains) and staying just one night is not enough. Also doing a 2 night stop instead of one, gives you some time to relax and walk around or drive around a bit in the area for a full day as you might end up arriving in Ortisei late afternoon.

raigContact - One more thing - If you do not, as you said have a huge draw for Venice - then I would add one more night to Tuscany - plenty to see there, cities or countryside, and lessen 1 night in Venice.

. A full day in Venice (2 nights' accommodation) would give you time to visit the lovely St Mark's Square and its Basilica, wander around the narrow street canals, do a gondola ride, have a nice coffee at the square in the evening in a cafeteria which also has an orchestra playing till very late in the evening (really beautiful atmosphere), and a couple of nice meals.

If possible do not make any 1-night stops.

GraigContact - do not lose heart - we went to Dolomites/Tuscany/Emilia Romagna (Rimini) last December, and still enjoyed it - and to Tuscany and Amalfi Coast in December 2010, and weather turned out to be beautiful - I guess weather is just a case of luck. In the southern Mediterranean, you often have a day or two of rainfall close to mid September, and then it might be lovely and sunny and hot again well into October. But you can never predict weather and rainfall any time of year (July and August are the safest bet - but it is the peak tourist and hottest season - not my cup of tea.

Also we have done holidays countless times with 3 kids, travelling around, the youngest with mobility problems.

So as they say, when there is a will there is a way. If you really want to see those places then go for it, especially since you say you enjoy driving, like my husband does, and do not want to visit every single attraction in the region.

My advice is (we have done this quite a few times but always found it not worthwhile to do - do NOT stay just 1 night in a place. At least do a 2 night stay.

But each to his own, I do understand that many love more relaxing holidays. Take into account everyone's recommendations and then do what you think suits you best.

Thank you Anna for all your insight and suggestions. I think we have it narrowed down, although changes can still be made.
You advice is right along the lines of how we like to travel, my wife said you were 'channeling' her. We tried to cut Como, but in the end we really wanted to experience it, if only for a short visit. Now we have to decide what to see at each stop!

Friday September 28th

Day 1 - Sat. 9/29 Arrive & stay in Rome
Rome55
Day 2 - Sun. 9/30 Travel to Positano (morning in Rome?)
Hotel Maricanto
Day 3 - Mon. 10/1 Positano
Day 4 - Tues. 10/2 Positano
Day 5 - Wed. 10/3 Travel to & stay in Montepulciano (Car rental)
Palazzo Carletti
Day 6 - Thurs. 10/4 Montepulciano
Day 7 - Fri. 10/5 Montepulciano
Day 8 - Sat. 10/6 Travel to Bellagio
Borgo Le Terrazze
Day 9 - Sun. 10/7 Bellagio
Day 10 - Mon. 10/8 Travel from Bellagio to Ortisei (via Stelvio Pass)
Hotel Digon
Day 11 - Tues. 10/9 Ortisei
Day 12 - Wed. 10/10 Travel from Ortisei to Bevilacqua (via Dolomites)
Relais Castello Bevilacqua
Day 13 - Thurs. 10/11 Bevilacqua
Day 14 - Fri. 10/12 Travel from Bevilacqua to Venice (Return rental car)
Al Redentore Di Venezia
Day 15 - Sat. 10/13 Venice
Day 16 - Sun. 10/14 Fly Home

Monday October 15th


I know this itinerary is not for everyone, but I think my wife and I will absolutely love it!

Craig - why don't you fly into Naples and then do travel and stops northwards - That way it would save you one Naples to Rome trip.

Would you like to spend some time in Rome? Your suggestion that in the morning you do Rome and then travel to Positano in the afternoon is questionable for me. You will be arriving late evening in Positano (probably you first have to reach Sorrento from Naples and then catch a bus to Positano, but I am not exactly sure, other Fodorites have to confirm this as we drove to Amalfi Coast), and I see you chose a lovely high-end hotel, pity to pay all that money and you arrive very late in the evening.

So how about flying into Naples and pick up car at airport. End of September beginning of October is not the very peak of season, as school would have started everywhere. Anyway, if you find it overwhelming (believe me we drove in more hair-raising hilltop towns and villages in Umbria and Tuscany, and if it there is traffic it is still not difficult to drive as you would be driving slowly), you can just park your car, I would think a hotel of that calibre would have parking facilites, and use public transport, but I doubt you would do that, as driving around is so very convenient, especially as a family.

Al the hotels you chose are soooo lovely, although I am not sure about the Venice one (although it also looks really beautiful), as it is not on the main Venice island, where there is the St. Mark's Square, and neither on mainland Venice. The hotel is on an island called Guideca Island. Remember that probably you are going to have an early flight from Venice to back home, so you have to check about vaporetto stops from this island during the night-time, or else maybe hire a private boat with drvier to take you to mainland Venice.

I notice that you added another stop, at Bevilaqua. The castle is really beautiful, and I am sure that you made that stop specifically to experience its ambience. I don't blame you, it does look lovely, in fact when I was browsing around last December for accomodation for our Christmas vacation in Italy, I came across this castle and I thought it looked lovely, but we preferred to base ourselves in Sud Tirol/Rimini/Umbria area.

I know that I am going against what I said earlier, but in your case, since you probably want to make a stop here, and you will be driving, which makes it much easier - why don't you just stay for 1 night at Bevilaqua, it is roughly on your way to Venice anyway and it might be interesting for you to make the stop and experience the place, and add 1 night to Rome,if you are determined to make a visit to Rome. That way at least you would have 2 nights in Rome and one full day to explore it, I know many Fodorites here would say it is too little, but if you really want to feel the Roman atmosphere, wander around its lovely squares, cafeteria and main streets, then go for it - book Bevilaqua castle with dinner for 1 night and add one night to Rome, more to see in Rome for sure. We did stay just 2 nights in Rome 4 years ago - we were brave enough (rather my husband) to drive all around the centre of the city - but since my daughter is disabled we are allowed to drive in restricted areas, and park in reserved parking for the disabled, but still driving in the very centr was not at all easy.

Anyway, on our 2 nights in Rome we managed to do a visit to the Vatican (have to say we skipped all queus since our daughter is disabled), we walked around the centre of Rome, near Spanish Steps, Fontana dei Trevi, and surrounding main streets, had a few lovely meals, and did an open bus tour around the main sites of Rome.

In Rome I would choose a hotel just on the outskirts of the centre Rome, with parking facilites, and preferably that do transfers to centre of Rome, or take a taxi or use public transport. If I were you I would not drive in centre of Rome, not easy at all, and you can so easily get fined as there are many one-way, restricted areas etc. But there are plenty of nice hotels just outside city centre.

So considering the type of holidays you enjoy doing (same goes for myself) I would do the vacation as follows:


Day 1 Sat - Fly to Naples airport - Pick up car at airport - Drive to Positano
(if you arrive quite early you might even stop stop in Pompeii, which is close to Naples,
get that visit over and done with. Alternatively
you can stop on your way back.

Drive to Positano

Day 2 Sun - Positano

Day 3 Mon - Positano

Day 4 Tue - Drive to Rome

Day 5 Wed - Rome

Day 6 Thu - Travel to & stay in Montepulcano

Day 7 Fri - Montepulciano

Day 8 Sat - Montepulciano

Day 9 Sun - Travel to Bellaggio

Day 10 Mon- Bellaggio

Day 11 Tue- Travel from Bellaggio to Ortisei

Day 12 Wed- Ortisei

Day 13 Thu- Travel from Ortisei to Bevilaqua

Day 14 Fri- Travel from Bevilaqua to Venice (on the way
doing a stop in Verona - or Padova)
Drop off rental car in Venice

Day 15 Sat- Venice

Day 16 Sun- Fly home

I also agree that this itinerary is not for everyone, but it certainly is also for me, lol. It is true you have many stops but I think you will still enjoy it on your way to reach them!!!

Craig - was thinking - if you prefer not to drive in Amalfi Coast you might be interested in picking up car from Naples after your stay in Positano. If you set off a bit early in the morning, right after breakfast, you might even have time to visit Pompei before starting your drive to Rome. It is a very easy drive from Naples to Rome, it would take you about one and a half hours.

I would eliminate Rome as it's just a waste of time to stay overnight and head out the next day.

>>>Day 5 - Wed. 10/3 Travel to & stay in Montepulciano (Car rental)<<<

Where do you plan to pick up your car? This will be a very long travel day.

kybourbon - I agree with you - that is why I suggested that he does Positano first (landing in Naples) and allocate 2 nights in Rome on the way to Montepulciano - that way OP would break the journey in Rome and still manage to fulfill his wish and make a visit to Rome for 2 nights.

As I suggested, he might wish to hire car on arrival or prior to leaving Naples, or even maybe, if OP wants to hire car after his 2 night visit to Rome, he might pick up car either at Rome's Fiumicino airport or (as many Fodorites here recommend) in Orvieto, taking train from Rome central station, and proceed by hired car to Montepulciano.

We had a very difficult time finding a flight that fit our budget/schedule into Naples, that is why we are arriving into Rome. The plan was to stay the night as our flight arrives in the evening. My thought was the next morning seeing the Spanish Steps & Trevi Fountain before taking the train south which is why I picked the location of the hotel in Rome.

Saying that, I am open to the idea of adding the extra day to Rome which is how I had it before when I considered not visiting Como. My wife is very intrigued by the castle so I am not sure if she would be willing to cut a night because we'd probably be arriving there late in the day after coming down from the Dolomites.

I agree that renting the car after Positano is most likely the way to go, I am looking into where but it does appear Naples would be the best bet...unless I can get one in Pompei as it looks like there are rental offices there(?) and kill two birds with one stone.

Thank you Anna once again for your insight, I really appreciate the advice for Venice. I will be looking into another location option that better fits with our schedule.

We rented our car in sorrento and it was easy enough to drive to umbria - although it took about 6 hours if I remember correctly...

Also by the time you add up the price of the transit into Rome and to Naples it may be close to the price difference in the flight...and flying would be simpler...just something to think about because I always forget to factor that in when comparing and also the lost vacation time...

Good point jamikins, we'll discuss that flight option for Naples and see if we can make it work. I will check Sorrento for car rental, I think that would be my preference.

>>>kybourbon - I agree with you - that is why I suggested that he does Positano first<<<

I was assuming flights were already booked since the OP is traveling in Sept.

Yes, Craig, if you do manage to fly to Naples that would be great - the best option. Another option might be to take a low cost flight from Rome to Naples, but I would retrieve my luggage and check-in again, to make sure they would not be lost in transit.

Yes, hiring a car from Sorrento is a good idea from Jamikins - from Sorrento you can drive on your route northwards to Pompeii for a short visit - in 2010 we did a 2-hour visit in Pompeii, just enough for the kids not to get too bored.

I checked on google maps, and from Pompeii to Montepulciano it is just a bit less than a 4 hours' drive. But I am assuming that you still wish to make a stop in Rome, and from Pompeii that would be about 2 hours' drive - or maybe you have decided to skip Rome altogether and drive to Montepulciano? I really do not think it is worth the hassle in visiting the centre of Rome for just one night, as it is not comparable to visiting a small town where you can drive right into the centre and to your hotel. If you make a stop in Pompeii, then you would be arriving late in the afternoon in Rome for sure, and I do think that Rome does deserve a 2 night stay.

Try to convince your wife to stay one night at the castle - it is lovely, I am sure, but I would not sacrifice 1 night in Como or Ortisei for it, the surroundings are too lovely and breathtakingly beautiful, and you would not be able to do a day trip in the areas. Always in my opinion, wandering a bit on the castle grounds in the afternoon before dinner and maybe spending some time in the morning would be enough. Maybe you can even leave early afternoon for Venice so that you might also spend the whole morning and have lunch at the castle. From Bevilacqua to Venice it is only a one and a half hours' drive.

.