Early Planning Stages - 20 nights in Italy

Arrive NAP
Curreri Viaggi bus from NAP to Sorrento
Sorrento: 4 - 5 nights at least. Use as. base for Pompeii, Amalfi coast, Capri, Naples, Procida and Ischia, etc.
Rome: 3-4 nights. May visit Orvieto from Rome.
Cinque Terre: 2 nights maybe 3.
Florence:3 nights very minimum. Use as base to visit Tuscany, including Pisa and Lucca.. Add one night to Florence for each day trip n Tuscany.
Bologna: 2 nights min. May use as base for Lamborghini and Ferrari.
Venice: 3 nights.
Lake Como (Varenna): 2-3 nights
Switzerland: via Bernina express and Luzern: 3-4 nights:
Milan: 2 nights.
I have already exceeded 24 nights. I gave you the minimums so you need to cut some places out. Can't fit everything in 24.

It can take longer than one might think to go from Italy to Switzerland, and you may find you need more than 4 days for that detour. Therefore, I suggest figuring out where you want to spend your Swiss time and checking train schedules from Venice to that location, and from that location back to Milan. Many people here especially like the small Alpine towns above Lauterbrunnen. Since you're on a budget, I'll issue the warning that Switzerland is very, very expensive. As soon as you decide where you'd like to be, you should start checking out the lodging options to see what you'll be letting yourself in for.

The Ferrari Museum can be visited from Modena or Bologna, though the trip would be quicker with a car than via public transportation. Bologna, though farther from the museum, is a particularly convenient transportation hub.

If you want an Alpine experience, the Italian side of the Alps might be more economical and save some travel time.

Apartments will be a nice option sometimes, but check out some B&Bs as well, they can be more economical.

Thanks for the comments so far. I am aware of how expensive Switzerland is, that is why Italy is being kept on such a tight budget. Travel time is being carefully considered also. This will just be a "taste of the Swiss Alps" visit.

I am more concerned right now about planning Italy. We have one family member who must eat strictly gluten-free, so this is part of the reason why we focus on apartments. While my research indicates that Italy does well with gluten-free, I am still leery of eating out too much. We have encountered too many mistakes at restaurants in the States.

Can Rome really be done in 3-4 days? I was thinking 5-6 minimum.

Will we regret skipping the Amalfi coast and C.T. and using that time to maybe base out of Bologna to explore the region around there, including the car museums? Is it reasonable to take a day trip to Florence from Bologna or would it just make more sense to stay in Florence a day or two?

I have read so many varying views on how much time to give Venice that I am at a loss on giving it just 2 days or giving it more.

We would love to include a few outdoor activities into our time, maybe some hiking, horseback riding, or zip lining. An affordable Agriturismo that would let us stay less than 7 days would also be of interest. Twenty days in just cities is too exhausting.

I am considering this a first trip to Italy - not an only trip to Italy, so I want to hit a enough places to give us a sense of where we might want to return without feeling so rushed that we do not enjoy the trip.

I would love to hear more ideas! Thank you!

I think we all have our eye on the list of places you're interested in and are trying to help you see them all, so we're not likely to suggest a week in Rome. It's always a balancing act--more places/more superficial vs. fewer places/more in-depth. The answer's different for different people.

I don't think I'd try to visit Florence from Bologna. There's just too much to do in Florence.

Since Pompeii is a must, you'll be quite close to the Amalfi area. A visit would certainly be possible. Where to trim? Personally, I'd cut Pisa to begin with. That will save about half a day (not nearly enough time for the Amalfi Drive, of course). Alternatively, you could head to the Cinque Terre, but check info on cruise ships in the nearby ports to try to avoid the most overrun days. Since you are traveling with teenagers, a destination that offers beach possibilities will probably be a big hit, and both coastal areas also offer stunning views very different from what you'll see at your other stops. There are good walks in both areas.

I'm a wander-around sort of traveler and would appreciate having more than two days in Venice. What you might do is book an extra night or two there and be prepared with day-trip possibilities in case you feel you've had enough Venice after two days. Verona, Padua, and Vicenza are all easily visited from Venice (probably one day apiece), though they make nice overnight stops as well.

Since you seem interested in a more in-depth experience with a mix of large and small destinations on this trip, you might consider limiting your itinerary to the northern part of the country and visiting Rome/Pompeii/Amalfi and other southern destinations on your next trip.

I eat gluten-free and Italy is very well aware of dietary restrictions. Children in Italy are tested for gluten sensitivity/celiac disease, and families receive a subsidy to help cover the cost of gluten-free ingredients, which are more expensive.

If you tell the waiter that you have a gluten problem, most likely the chef will come out to recommend something. No need to cook in to avoid contamination. I have eaten at restaurants where the chef explains that the kitchen must be decontaminated, so it will take a little longer for our meals to arrive. Some places (including gelaterie) will have specific utensils and cookware for gluten-free cooking. Magic words are "senza glutine".

If you decide to cook gluten-free, most grocery stores (and some pharmacies) have gluten-free sections.

Sorry, I don't have any specific recommendations, but just a few thoughts.
I don't think you'll regret not staying on the Amalfi Coast (proper). If you can budget a three night stay in Sorrento immediately following your arrival in Naples, you could take a day trip by ferry to Positano (which might be a good way to spend your first full day) and then go to Pompeii the next day.
For your Tuscany leg, you could consider basing yourself in Lucca. You could visit Pisa from there, and have a classic Italian beach experience in Viareggio. If your teenagers are up for a long day of sightseeing, you could also take a day trip to Florence from there. I agree with others that you won't even scratch the surface of Florence in one day, but you can get a good preview for a future trip.
If you wanted to rent a car, you could consider staying at an agriturismo in Emilia-Romagna. You could visit the car museums from there, and there is quite a lot of equestrian tourism in the area.

I would budget three full days in Venice - I was there last October, and there seemed to be a lot of teenagers there on family and school trips, and really enjoying themselves. It is a very interesting place, completely apart from all of the sights of historical interest.
Finally, while I respect your desire to go to Switzerland - perhaps one of your kids wants to visit there - a trip to the Italian or Austrian alps makes much more sense in the context of this trip, and would allow more flexibility.

Since you are flying to Naples, it makes no sense to eliminate visiting the Amalfi Coast. You are in the area anyhow because you want to visit Pompeii, therefore you might as well kill several birds with one stone. Just stay in Sorrento, which will give you easy access to Pompeii, Amalfi Coast (Positano), Capri island, etc.. If you stay at least 4 nights, you can see all. 4 nights is 3 full days. One day Amalfi coast excursion (by bus or boat from Sorrento), one day excursion to Capri (by boat), 1/2 day visit Pompeii (the remaining 1/2 day you could visit the museum in Naples, if you want. Also you could visit Pompeii (and Naples, on your way to Rome (just leave Sorrento in the morning, visit Pompeii and Naples along the way, then go to Rome in the late afternoon).

Cinque Terre is a good candidate for elimination. You are already doing the Amalfi coast, which is similar, and the Cinque Terre is hard to reach.

3 nights in Rome is the minimum. 4 is ideal in a 20 day visit.

Florence is a must, IMO. Florence requires at least couple of days to visit the most salient places. Pisa could easily be dumped in my book. If it's a must for you, you can visit it from Florence (only 1 hr away by train, and almost 60 trains a day in each direction). If you go to Pisa, you should visit nearby Lucca also, and actually spend more time in Lucca. Pisa is a one trick town and in 1 or 2 hours you can see everything there is to see. I'd book 2 nights (1.5 days) just for Florence. Then add one night for each day trip. For example with one extra night you can visit Pisa+Lucca. With 2 extra nights you can add a day trip to Siena. And so on depending on how many day trips you want to take within Tuscany.

Bologna can be used as a base for the car museums, but give yourself a few hours for Bologna itself. A couple of nights should be sufficient for everything. That will give you 1.5 days. 1 day for the museum(s) and the rest for Bologna.

Venice can be done in 3 nights. To me that is the ideal length of time in the context of a 3 week vacation. Actually you should also have time for Murano and Burano in that length of time.

Lake Como is a bit of a detour. If you go to Lake Como, I wouldn't spend more than 3 nights. 2 might be enough in fact. You might also consider Lake Garda instead, which is closer to Venice, and which also is very close to Verona, a beautiful small city.

Switzerland is an expensive detour. But if you want to do it, do it.

Since "...this a first trip to Italy - not an only trip to Italy...", consider scaling back a bit. You've listed six "must sees" and four other possibilities. The reason for this suggestion is that it almost always takes longer to go from Location A to Location B than one anticipates. You want to come back with memories of people, place, things, and sight -- not just memories of train stations. What you are proposing is doable, but will be quite exhausting. Don't mean to be a "downer" -- just something to think about.

Rome can be done in three or four days. But five to six full days will be better as you will have time for a short day trip or two.

Since you are flying into Naples, you will be close to the Amalfi coast and I think I'd give it a couple of days.

Since twenty days in cities will be too exhausting, consider Lake Como. Very relaxing place to R & R.

Venice, imo, deserves a minimum of three full days and four would be even better.

As you start cutting, adding places, and roughing out an itinerary, be sure to get the girls input. Teen daughters might surprise you with their ideas.

Fabulous insight from everyone - thank you - especially the gluten-free comments. The girls are a big part of the planning and are driving the "must-sees". It ends up then being mom's responsibility to figure out how to make it all work without making us all crazy.

I really had not given much thought to Sorrento and surrounding areas. Our original intent was to spend two nights in Naples, affording us just enough time to visit Pompeii and maybe the archaeological museum before heading to Rome. It sounds like I need to reconsider that and maybe shave back Rome to accommodate that.

Pisa is a teen request. I get that it is something that could easily be ditched, but is high on the girls' list of priorities, so I will make it work. I think dropping C.T. makes sense. I was not too excited about the potential crowds anyhow.

I was also toying with trying to hit the car museums as a day trip from Florence just to limit the amount of transferring from lodging to lodging we do. It looked like it might be doable, but maybe better to consider it en route to Venice.

I really appreciate the feedback on how much time with need in Venice. That has been one of the biggest question marks for me. I can see us enjoying that city.

I appreciate the suggestions to stick to the Italian or even Austrian Alps. however we are hoping to connect with an old friend in Switzerland. I am considering flights from Venice to mitigate some of the travel time issues. I am leaving that portion of the trip open for now.

Your comments are helping me to narrow my focus and to try to keep the trip manageable. On our last European trip we only went to 2 cities and stayed a week in each. That was nice. But, with so much to do in Italy, it does not seem feasible to move so few times on this trip.

For more about Italy and celiacs, here is a thread; in it, there are lots of links to other threads on the topic, as well as to a very informative New York Times article. You'll see that Italy is just about the most gluten-aware place around.

https://community.ricksteves.com/travel-forum/italy/gluten-free-in-italy-4b508a80-3aab-47a7-85c4-e44ab8dfd77c

One thing to keep in mind for side-trips to small towns is that bus service tends to be thin to non-existent on Sundays and holidays in Italy. Be very careful not to schedule a move that must be made by bus on a Sunday or holiday unless you find really iron-clad evidence that buses will be available. Minor train routes are often cut back on Sundays and holidays as well.

MP, We plan on being in Italy for "only" 16 days next summer with our teen. One thing I'm considering is a day trip with a driver from Naples (we would catch the early morning train from Rome--about an hour and a bit), the driver meets us at the station, takes us to Pompeii (can arrange for a guide if we want), then takes us around Sorrento and Positano with a lunch in between up in the hills. Then train back to Rome. The TripAdvisor reviews are terrific. https://seeamalficoast.com. Not cheap, but you're also not paying for a hotel on the AC.

We are flying into Venice for 2 nights, Florence (3 nights), Tuscany (near Pienza) for 5 nights (pool and village tour time!), 2 nights CT, then 4 nights Rome, then back to US.

We did a similar trip to France in 2015 and did some fun things that were a big hit with my son: fat tire bike tours, kayaking under the Pont du Gard, etc., and looking for similar in Italy.

acraven - excellent reminder! Thank you.

ksinclair - I had not thought about a driver. I will explore that option.

The wonderfully varied views are what make this forum so great! Thank you for the additional ideas.