"I don't think Mme travels with anyone,..."

Incorrect. I have, in fact, taken "neophyte" travelers along and, while everything didn't always go as planned, I also didn't worry that much when someone decided to go rogue for a while. I just let them go and they always came back. I figured they were a grown-ups, proceeded with plans, no one ever "blamed" me for their own adventures, the sky didn't fall and we live to tell the tale. I think they had a great time exercising their own spontaneity and I advise the OP to breath deeply, plan as best she can, expect there will be deviations from plan, keep it simple and even try to relax enough to enjoy herself, too.

I suggest she not try to "herd" and two cities is not "around Europe".

Just go for it!

The pros:
1. It will be a wonderful learning experience as far as travel planning is concerned
2. It will be a wonderful learning experience as far as your chosen cities are concerned as you will truly have to immerse yourself to get everything to work to plan
3. If you successfully pull it off your cred in the family will be amazing
4. Something is bound to go wrong so if you are calm you will learn the Italian art or arrangiarsi
5. Think of how many of the Fodors posters will be upset when you post a trip report showing how well things worked out (tip: you don't have to post a trip report if the opposite is true!)

The cons:
1. If there are major problems, especially if due to lack of planning, your cred may end up in the pits
2. Your family may hate you before, during and after the trip.

If I was your age I would go for it in a flash. In fact I would start tomorrow if I had to arrange a similar trip somewhere outside of Europe. Which, in fact, I did in summer 2014 and I have done for a party visiting multiple Greek Isles for the last 5 years.

Nochblad, here here!

I'll just add, those family members who will hate you will find an excuse no matter what, trip or no trip. Bask in the love of those who love you, no matter what.

MmePerdu -"I don't think Mme travels with anyone,..."

I would but I don't think this is the right forum ....

Well, we might do a workaround...and I appreciate the thought.

My main advice is to be flexible on what people do. Way back in 1990, I did a 2 week tour around Europe with my parents, 2 siblings and my grandparents. My sister and I were in college and graduate school at the time. We had a van and did the trip everyone here always says is awful. We hit something like 7 countries. We were never anywhere for more than two nights, and most places only one night. This was/is just the way my family traveled. I didn't mind the pace, but what was a struggle was my mother's insistence that we ALL do what ever was planned for the day together. As young 20 somethings this was difficult for my sister and me. And in general, with a group that spans several generations interests will be varied.

Now I travel more slowly. I agree that two locations is probably the best. I also think if you want to visit major cities, taking a train between would be easier.

(Correction, it should have been "hear hear".)

I think the OP should take along Mme.

Both fully planned guided tour and self planned possible chaos have drawbacks. Perhaps a hybrid:

Self plan travel and hotels, open jaw flights in or out of Rome and one other place (Venice or Florence), and train between. Local guided day tours in each place, arranged easily by hotel, and group could split into different tours depending on interests and mood. Meet up for dinner. Guidebook self touring as desired. Fun, much less stress.

I've several times organized trips for my family, with up to seven people. I'm usually paying for almost everything, which really cuts down on the complaints.

Last year I organized a trip for my husband and me, and another couple. The man was a friend of my husband since university days, and we have had numerous outings with the other couple over the years, but not overnight trips. We never came to blows, but by the end of the trip we didn't care if we never saw them again, and they probably felt the same way about us. However, we've got our friendship back on track and have had several more pleasant times together.

I'm certain that if we'd been sharing an apartment, it would have been much more difficult. At least we had plenty of separation at night.

I have another friend who went on a trip with a lifelong friend, and they haven't spoken since. They stayed in apartments, and one of the issues was "who gets the best bedroom". Another was the splitting of the cost of restaurant meals. It's really best to establish the rules of these things before setting out.

I organized a trip a few years ago for my book club . . . I am still friendly w/ everyone who was on the trip except for one who I don't care if I ever see again in this life time >) In fact I've traveled with 3 of them on different trips to other places since.

But the trip caused so many rifts between others that the book club, which had been running for about 10 years, broke up within about 3 months.

Now, not every group trip ends badly/sadly/armed conflict. Not by a long shot. But group dynamics are a funny thing. Especially when everyone is in close quarters and unfamiliar situations.

I have taken groups of friends and family to Italy quite a few times in the last fifteen years. What I have found that works best is to rent a 9 passenger van for most transportation. We generally rent a villa in Tuscany, just south of Siena, and take day trips to the many hill towns and wineries in the area; any place within a 90 minute drive. There are usually between 7 to 9 people along,and we have had many interesting experiences, but none that I would characterize as unpleasant. Still talking to everyone. We have also visited the larger cities; Rome, Milan, Venice, but have found those places less successful with a larger group.

We have some friends who belonged to a "salon" that had been having meetings, lectures, dinners, and cultural trips for twenty years. Then, on one particular trip, the kitty came up short for the cost of a restaurant meal, and one member accused another of not having put in her share. All hell broke loose and twenty years of petty resentments, irks, and grudges were soon flying through the air. That was the end of the salon.

Bvlenci . . . I can only imagine! :). I know of what you speak.

By the way, you don't need a special license in Italy to drive a van with up to nine passengers. You do need an International Drivers Permit (IDP), along with your regular license. (This is true if you'll be driving any vehicle.) You can get the IDP at an AAA office. Bring along some passport-sized photos, or let them take the photos, at extra cost.