I am taking my family (10 people total) to Italy – 16 days total – help.

First,
Is your count full days in each city or are they nights? Or does this day count have to include getting from one place to the next? (i.e. arrive in Rome is Day 1, then you have Days 2 & 3, meaning you would have 2 1/2 days) Counting nights helps me get a better idea of the actual time on the ground I will have.

Next, I have taken a group of 13 people for 10 days (8 nights). It helps me to have lodging either in easy proximity to city centers or next to easy public transportation. You, of course, have to juggle that with appropriate lodging. Especially with Rome, this might mean you need a bit more time. Things are just SO much slower with a group.

I wince at the thought of 2 vehicles and suggest you go ahead and put trains in your plan and make whatever compromise you have to make in order to do so.

It is exciting to show our family the places we love! Just remember that Italy is wonderful and they will have a great time - but it won’t be the same as when you travel on your own.

I have twice taken groups of 7 to Europe-once to Greece and once to Italy. A few observations.

1. I would stay where you can rely on public transportation and as close to city center as you can logistically. You have to think that everyone isn’t going to always be together and you want to make it possible for people to do different things. You also aren’t going to find a van big enough and public transportation is much easier . This means that you won’t be able to go to some places I realize but there are many wonderful places you can go.

2. I haven’t been to Cinque Terre but decided to go to Lake Como with our crew instead. Everyone loved it there. It would be something to consider. You could fly into Milan and out of Rome.

3. I think 3 nights in Rome is not enough especially with a large group and when jet lagged. I would put Rome last not first.

4. Rather than staying in small towns in Tuscany and needing a car to see many things, consider adding a stop in Orvieto which can be reached by train .

The Cinque Terre is your most northern point and the closest airports are Genoa (1h 45m), Pisa (1h 45), Florence (2h 15m) and Milan (3h 30m). Consider flying into or out of one these cities. Don’t plan on sight-seeing on arrival day, use that day to settle in. Remember, it’s normal not to sleep on the flight over.
Rome needs a minimum of four nights if you visit Vatican City. If possible, sleep in the Trastevere neighborhood not outside of Rome.
Siena will make a nice base for Tuscany and Florence. If you hire a driver to take you to the Cinque Terre, sleep there not La Spezia. If you’re taking the train, it might be easier to sleep in La Spezia. You learn more about a place when you spend the night vs. taking a day trip.

I suspect you really only have 12 nights in the country. Please confirm!

If this is correct, try to whittle the itinerary down to 3 places for your group to lay their heads. Consider Rome, Cinque Terre, then Florence with day trips to hill towns OR stay up in Fiesole (close but above Florence) so you have easy access to Florence for departure if you are flying out of there. Rome to the Cinque Terre is easy with a direct train to La Spezia. Staying in La Spezia is not a bad idea with a large group, BTW.

Your final itinerary depends on time of year as well. In summer, your needs are different then shoulder season. Do you have a month in mind?

With your large group, finding a village outside Rome is not a good idea. You would have to take public transport every day, wasting time and money. Stay in Rome and see that wonderful city, it is very walkable.

Florence is great, you can do a day trip to Siena.

Personally, I like the Amalfi Coast more than Cinque Terre.

Driving with two vehicles in Italy, considering parking and the likelihood of getting an expensive ticket, forget that.

I concur with staying in city centers. If I was on this trip with you, or any tour, I would want to have the option of going out on my own, even if just for a short walk or a coffee. I would not want to be so tied to the group that I would have to wait for the whole crew to assemble to take a ride into city center. I am sure your group will have some independents and probably a few very dependents.
I do not envy your task.
I think you should have a group meeting and discuss some of this with them. Do not assume that you know everyone and their views on the trip. These are people never in Europe, so probably very little travel experiences, but they may have big and unrealistic expectations. That is trouble my friend, right there in River City.

With such a large group of different generations, I would stay in the historical centers of Florence and Rome. This way no need to travel in and out each day. Make this as easy and painless as possible. People will have plenty of choices for meals and sight seeing and the big group can breakdown into little groups and do what they want. Sometimes with that many people, hotel rooms can be a blessing. A place to get away from the others in the group.

I organized a two-family trip for 10 to Spain earlier this year, and we had so much fun that we are all going to Greece next summer and bringing along 2 more.

I haven't been to the places you are planning to go in Italy, so I can't offer any suggestions specific to those locations, but I can give you some lessons learned from traveling with a big group (which was awesome; we really had a great time):

1) Most important -- don't expect everyone to do everything together. Actively plan to split up into smaller groups and let people find their own way at their own pace. So, if you are planning a museum visit, meet up and start at the same time, but expect/suggest that family members break up into groups during the visit (who likes to read every sign? who likes to skim? who wants to focus on one area? who likes to hang out at the cafe?), and pick a time/place to meet up later in the day.

2) Figure out an eating plan each day. Talk about when you will all eat together and when you will "find your own." For our group, it worked really well to have a group breakfast in one of the apartments (whoever had the biggest kitchen "hosted" while we were in that town), then divide and conquer for the day, then meet back up for dinner, either cooking together in the apartment (which was a lot of fun) or at a restaurant. If planning a restaurant meal, make sure to get reservations -- a group of 10 is tough to just walk in with.

3) As BethFL mentioned, stay in central locations within walking distance or public transportation access of places you want to see -- and restaurants, coffee shops, and bars. That way, your family members can find their own way at their own pace; no one needs to wait around for a rideshare.

4) Use your phones to communicate. Make sure at least one person in each small group has a data plan and can text. We also had everyone sharing location on our iPhones -- all 10 of us, even the ones who were not using data. This really helped so we could figure out where we all were and could group up a lot more efficiently when we were trying to get back together at the end of the day.

5) Take advantage of private transfers. They aren't necessarily prohibitively expensive; you can realize economies of scale with a group this size. We used public transportation (trains/busses) when it made sense, but in a couple of places, it was a lot more efficient to hire a private driver/minibus at a cost very close to public transport.

Have fun planning your trip -- I'm sure you will have a great adventure!

You haven’t said when you plan to go but I just ran a quick check using VRBO for 10 people in Central Rome in mid May 2023 and there are a few options for about $80 per night per person for 10 people. I prefer to stay in towns as I get a more authentic experience and I enjoy going out for meals. I get enough experience of juggling my wife’s interests and abilities and my own without trying to juggle those of 10 people.
You’ll require reservations at most restaurants to accommodate 10 people as reasonable restaurants often are fully booked and I wouldn’t want to be walking around any town or city trying to get 10 people in to eat. It can be frustrating even for 2 of us. We”re in Orvieto now and I had made reservations a week ago for last night and the restaurant was full with a sign on the door advising of this fact and turning away people who were walking up.
Who’s paying for this trip? Having organized group hiking trips in Alberta, BC and Montana for up to 24 people for 4 nights, one of main problems was getting financial commitments from the participants sometimes just for the accommodation and other times the meals were included. If you book a VRBO based on 10 people who covers the extra per person cost it a couple cancel? As people expressed interest in a bike and barge trip in France, I made a tentative booking for 12 people but only 2 other couples signed up in the 1 week time limit. By insisting that they deal directly with the bike and barge operator, when they had to change their plans to go the week before, it wasn’t my problem.
Good luck and hope it turns out well.

I have no experience arranging such a trip; I commend your guts and generosity. You've gotten really brilliant suggestions already.

I'm wondering about the time in/near Cinque Terre. Are there other places you plan to go in that area in addition to the five villages? Does your group include folks with mobility limitations? If some cannot climb up to the walking paths and/or have a problem with heights, are they going to have enough to do? Have you been to Cinque Terre fairly recently, or is it a place you visited very early during your European travels--i.e., close to 20 years ago? I haven't been there for a very, very long time, but by all accounts it's a mob scene during the busy season. It doesn't sound like the sort of place I'd want to take a large family group today. There are other towns in that area that might be better, or you could consider the Amalfi Coast or Lake Como as your scenic stop. Both of those are touristy, I know, but they shouldn't be as unremittingly packed as the Cinque Terre in high season.

With a group this size you should be able to get a good deal on a private tour of Tuscan villages so you can see several small places in a single day without dealing with challenging public-transportation schedules.

Be careful about the details if you proceed with the idea of using houses or large apartments. I understand the attraction of having everyone together, but you need to be sure you have enough bathrooms and real beds--not futons and fold-out couches.

Wow, so many good tips, Eddie! I'll agree with the following:

1. Stay in the historic centers and not outside of them!!! Otherwise, you'd waste a lot of time/money on transport, and are a long way from your lodgings if someone forgets something important or needs a break. The less daily moving about by transport, the better.

2. Don't plan on doing everything together...which is another reason to stay in the city centers. That'll make it easy for some of your gang to wander off on their own, such as for some exploring after dark when others might be too pooped for any more wear on their feet.

3. Bag the rental-vehicle idea and use public transport. You do NOT want to drive the things into or around the cities, and don't need them if you stay IN the cities. Travel like many Italians do: by rail and, sometimes, bus. Also, I don't know firsthand what the situation is currently but car rental and gas prices have been reported by some forum posters to be pretty nasty in Europe lately. The way I see it, rail travel is part of an Italian Adventure as so many of us here in the US don't have that convenience.

4. Don't plan this whole thing by yourself. If your other 9 travel companions are adults, they should help. If everyone has a hand in the plan, it reduces the amount of potential complaints from any members who may not appreciate the plan or the work that went into it. :O)

5. I like the idea of spreading your group out amongst separate hotel rooms, at least for part of the trip. Along with being easier to book - finding properties in the cities which could accommodate all of you could be a challenge - a little less "togetherness" here and there may be welcome. Do pay attention to acraven's excellent caution about apartments that count fold-out couches and whatnot located shared public spaces as "beds". No one wants to sleep in the living room, and 2 bathrooms for 10 is not enough if you all have to be up, fed, dressed and out the door for a morning tour or to catch a train.

6. Landing tickets for a group of 10 may be difficult, as many of the most-visited attractions now mandate advance, timed-entry reservations. As well, some have a limit on how many tickets one can reserve at the same time. For attractions such as the Colosseum, Vatican Museums, Uffizi and some other stuff, I'd look into private guides who can handle that for you plus the herding about of your large group. While more expensive up front than general-entry tickets, I think the cost will even out nicely when averaged across nearly a dozen people, and be WELL worth it for the convenience. Plus, it take the pressure off you to have to play tour guide!

7. I am counting 14 nights, 13 FULL days + 1 partial, jet-lagged arrival day. I would personally choose no more than 3 bases, as moving 10 people around will be challenging enough but you already knew that, eh? You'll need to be in your city of departure the night before your flight.

Also, you haven't mentioned what time of year you're planning to do this? I'm asking because city sightseeing can be especially wearing in the summer heat, and CT isn't a great location in the colder months. Regardless, I'd add definitely add more time to Rome, and take a night away from the CT (if you keep that one) unless you're all interested in hiking. Consider Levanto versus La Spezia if preferring to stay on the edge of that region: people who do seem to like that one a bit better.

I appreciate the responses. I spent some time the last week thinking through the complexities of luggage/travel logistics and even driving cars vs. trains. You have me thinking I should cut this down to just two cities - Rome and Florence.

Rome 6 nights/days
Florence 8 nights

We are going in early June/summer. We can get AirBnBs at each location, with each having multiple beds/baths & of course, living rooms/kitchens/space. All will be near the city center and core attractions.

We can then rely on guided tour buses to see all the other stuff outside these two core cities. Some examples I found…..
Pompei/Positano (full-day guided bus tour out of Rome)
Assisi & Orvieto (full-day guided bus tour out of Rome)
Siena/San Gimignano (full-day guided bus tour out of Florence)
Cinque Terre (full-day guided bus tour out of Florence)
Montepulciano/Wine Tour (full-day guided but tour out of Florence)

So, five days doing early morning, full-day guided bus tours from Rome & Florence, and the other eight full days will be seeing the major sites in the city via prepaid/planned tickets or group tours.

My downside to this idea is doing the group bus tours since I have seen Italy and want to spend more time in those cities/places (and bus tours are generally not my thing). But I must remember it is all new to them, and we can use the extra bus driving time to interact and have fun. This also allows people to decide whether to go or not on any group tour independently. This also seems to eliminate many travel logistic worries and allows me to relax as much as possible since the guided tour people have to drive and preplan everything.

As of now, eight people confirmed, and eight more are seriously considering it, so we might have more people than I thought. This is another reason to minimize all travel and allow as much flexibility for certain groups to say yes/no to any specific event while also giving each group the responsibility to pay for as many tours/things as possible.

Any ideas or suggestions would be appreciated, and this is exciting. Imagine taking family or close friends to Europe/Italy, most of whom have never been before.

I think setting up base camp just twice is a very smart move. There are certainly plenty of sights to see in those two major cities, plus all the side-trip possibilities. I would recommend against combining Orvieto and Assisi, though. Like you, I don't like being given only a short time at a major destination. Orvieto has a lot of quality sights; it isn't just a cute hill town. I'd make a full-day trip there by train. That's easy enough to do, and it will be a lot cheaper than paying for a rushed tour to two cities.

I liked Assisi a lot but only spent some hours there (vs. multiple days in Orvieto). I'm therefore less equipped to make a good argument for the inadequacy of a two-city bus tour from Rome when folks want to see Assisi. I'll just note that I started at the top of the town and wandered downhill through the charming, atmospheric, medieval streets. I saw few other tourists until I got quite close to the basilica (which is truly gorgeous inside, and large) and began encountering the ticky-tacky religious-souvenir shops. I'm very afraid that an Orvieto+Assisi bus tour wouldn't allow time for much more than the very worthwhile basilica and not-so-attractive area immediately around it.

I did some very quick-and-dirty research on travel time for an Orvieto+Assisi tour. ViaMichelin.com estimates the total driving time at about 5-1/2 hours--clearly leaving very little feet-on-the-ground time to be split between those two wonderful towns. And that travel time doesn't allow for bus loading and unloading time, or time spent picking up and dropping off customers at various locations in Rome (which is the way some such tours work). At the very least, if you feel you must tackle these two cities via a bus tour, I'd try to arrange a private tour for the members of your family who want to participate. It still won't be what I'd enjoy, but needs must.

I've never been to Pompeii or Positano, but the transportation issues for that sort of combo tour seem even worse: ViaMichelin estimates 7 hr. 14 min. by road! That's just crazy. If you must visit Pompeii from Rome (and I know a lot of folks feel it's a must-see), the way to do it is to start with the fast (Freccia) train to Naples. You have some options in Naples and could arrange to take a bus tour from that point if you don't want to deal with the Circumvesuviana local train that has a stop very near the excavations.

Pompei/Positano (full-day guided bus tour out of Rome)

I think it would be a much better plan go to Ostia Antica. Much closer and manageable by the Metro from Rome.

I have not done research, but what does a bus tour of Cinque Terre cover and how close any of the villages does it really get? Are you sure it will do what you want it to do?

If you were to do 6 nights Florence, 2 nights CT and last 6 nights in Rome it could be a manageable way to get your "Italian seaside" experience in your time frame. Positano is just too far the 'wrong way', for where the rest of your travels are.

Unless your group is all within the 15-60 age range, all day bus rides will almost certainly produce frowns on some faces.

I admire your taking on this kind of challenge

Good luck

I can’t imagine why you would need a guided tour of the Cinque Terre. There’s not that much to see that a guide would enhance. Also, three days is too much time there.
Having two cars is a really good idea for a couple of reasons . First, it may be cheaper than a large van. Secondly, maneuvering and parking a large vehicle in some towns is not easy.

Also, having two vehicles will allow people to have choices about what they want to do.

ACraven - I had not thought about the day trips that way and it is a much better idea. We can take a train to Orvieto and spend hours including lunch there and skip Assisi and/or a bus tour.

I also agree that Pompeii/Positano is way too far from Rome. I was just wanting them to see something on the Amalfi Coast but not needed.

Cinque Terre bus tour is only for the logistics so it is not that the tour guide offers value = it is the bus that drops you off at a strategic location and picks you up at another strategic location so you can enjoy 3 of the 5 cities. I will probably keep that bus tour because I want them to see the ocean once during the trip.

I haven't been to the Cinque Terre for decades, and the visitor experience has changed massively (not for the better, alas) over that period, but I'm not sure the bus tour will help much. The villages are connected by train. It's not a quick trip from Florence, but the bus ride won't be quick, either (though possibly somewhat faster than the train). There's a train departure at 7:28 AM that gets you to the southernmost of the towns, Riomaggiore, at 10:02 after transfers in Pisa and La Spezia. The train line through the villages has been there a lot longer than the road, and I like the idea of traveling as you used to have to, if you didn't have a boat.

The villages can be overwhelmed with day-trippers, so I'd consider it an advantage to be able to set your own schedule in the area rather than adhering to a bus company's schedule. In addition, many people have suggested using the ferry in order to get a view of the villages from the sea (probably the most scenic view unless your group is going to climb way up to the hiking trail and walk along it--and I'm not sure all four segments are currently open. I haven't taken the ferry, but it sounds like an excellent idea to me.

I hope at least a few folks who've been to the Cinque Terre recently will give their opinions about the advantages and disadvantages of various transportation methods to and within the area..

I did not read all the replies so I apologize if this has been covered. We took eight adult "children" to Italy this past summer for a total of 10 adults. Like you it was my lifelong dream. It had challenges and blessings. We rented a villa about 3 miles outside of San Gimigmano (5 bedroom/5 bath house) which I would recommend as long as you have cars to transport everyone. https://www.lazzarona.it/ We rented through VRBO but I believe you can book directly. It is just as the pictures show. Taxis were few and far between. The villa has two train stations near by and we took (together and separate) day trips to Pisa, Florence, Siena, etc.

We also took all 10 of us to Cinque Terra for the day via train. We rented a boat (with captain) and it was perfect. We have been to CT a few times but wanted to show it to the kids and we opted for seeing it from the water to avoid the crowds. We were able to go into any village we wanted. https://www.cinqueterreadventure.com/ Cinque Terra Adventures were excellent.

Make sure everyone knows before they leave home that they will have to handle their own luggage on trains without being able to check it or get assistance from porters.

People will say "don't do it" but if your stay in Rome is long enough, anyone that really wants to do Pompeii/Amalfi can take a very long day bus tour.-maybe 13 hours. My 70 yr old inlaws and I did it in 1997 and we were all fine with it. I would do it again.

In 2019 I took a bus tour from Rome to Orvieto and Assisi. I loved Orvieto but don't feel I would have missed anything by not seeing Assisi. People with different religious views may feel differently about Assisi.

There are beaches one hour from Rome by train. Santa Marinella, Santa Severa, and Fregene. Lovely places and great restaurants.

Eddie, I like the idea of 6 nights in central Rome and 8 in central Florence, especially if you could end up with a group even larger than 10! The more autonomy you can provide a tribe of this size, the better.

Like some of the others, I don't see the need for an escorted bus tour to either Orvieto or Siena. Use guidebooks and take the train so you can enjoy rambling about on your own schedule. Maybe keep the wine tour; it's possible that not everyone will want to do that one and may prefer to head off from Florence to Pisa, Fiesole, Lucca, etc. Keeping a large group together in the CT could be interesting if the villages are VERY busy. Same with trying to get everyone on/off ferries and trains at the same time.

While some people certainly do it, I'd personally find a road trip to Pompeii/Positano from Rome to be a miserably long day. IMHO, the bus/vehicle tours spend too much time on the road compared to the sightseeing time. Pompeii is a vast excavation that deserves more than a couple of hours; save it for another trip when you can spend quality time In the Naples/Sorrentine/Amalfi Coast region.

Ostia Antica is a great substitute as it's smaller and much closer to Rome.

As said earlier, I'd definitely look into a private guide for the Colosseum/Palatine/Forum, and the Vatican Museums. Along with the complexity of the archeology (Forum/Palatine) and sheer size of the museums, trying to land individual, timed-entry tickets for a group your size would be a pain in the butt, and I think it would be an economical choice besides. You could do the same for the Uffizi in Florence, if it's on practically everyone's list.