This Itinerary is getting the best of us!

This is pretty easy to settle down - get a large piece of paper - draw out a calendar, with dates - plunk in your arrival and departure dates, those are fixed - then unfold the map and draw out a route that flows from start to finish. Easy Peasy.

yes our mistake was not starting south and working our way north. We fly in to Florence.

I think your primary issue is not so much about an itinerary, but more about friendship, boundaries and trade-offs.

You are trying to accommodate your first-time friend somewhat, but you don't want to "re-do" places you've been to before. That's the rub. You need to come to some understanding, accepting what you are willing to "re-do" and what you're not. You can't make decisions without first knowing how much you're willing to re-do and your limits. Without that, it's going to be hard (impossible?) to make reasonable choices.

Once you settle on some guideline for how much "re-doing" is OK, then the rest are just minor implementation details.

On top of that, you are planning to fly in to Florence, which is geographically "central" (more or less) to most of northern Italy's popular attractions. So, yes, that means lots of backtracking. Are you sure you want to fly in to Florence? If yes, accept that the "backtracking" is part of the package you signed up for.

Hate backtracking? Then maybe switch to fly in to Rome and proceed north from there?

THEN ... immediately go South from Florence and map out the route north with the full knowledge that not everything is doable ... get some consensus with in the group for what is doable and make the big picture a small picture. This all looks pretty easy to me.

You are right - all of you! It is a dilemma, and I gues the one place I would say we don't want to redo is Venice. We already have tickets to fly in to Florence. So either we should restructure the entire trip if our apartment will let us change dates and is available. Otherwise, I guess head to Orvieto, then Rome, then .......back north somewhere. Possibly fly back to Paris from Milan. We know its four hours going back north on a train to say Varenna or Cinque Terre the onward to Milan for a flight. Originally we were going to do Florence for five nights, then go to Varenna for two then the Bernina Express and try and move on to Alsace. Friend thought 8 hours on the train was excessive...so back to the drawing board.

I would rent a car in Florence and drive south toward Rome exploring areas of Tuscany (or also Umbria) you haven’t seen before. Maremma comes to mind, but options are vast. Your friend will get to see areas that most Americans don’t ever visit and that are new to you as well. Then fly to Paris from Rome.

Roberto - that is probably a good idea. Just now have to find places where a car won't be a hinderance. Where in Rome would you turn the car in at? And then there are those darn drop off fees.....ug

Just because something has been "decided" doesn't mean it's wrong to change plans. Even if you have tickets. Even if the costs go up.

You need to weigh your options, and be realistic. Compare your best "Plan A" (with your existing reservations) to your best "Plan B", taking into account any cancellation fees or other expenses you might incur. But weigh your options honestly, including the benefits and drawbacks of each. Sometimes, you need to stick with an imperfect plan (because switching would cost too much and not provide enough benefit). But sometimes, you can come up with a better Plan B and it may not ultimately cost more, or it may cost a bit more but it'll be worth it to pay a little extra because of other benefits that will make the cost justifiable. If you have limited time, that's worth factoring in too.

So get out your sharp pencil, look at your options, take a sober look and decide what's best for you. Sometimes that's sticking with Plan A, but sometimes Plan B may be a better choice even if it costs some more. Only you can decide.

Consider visiting Umbria:
Perugia, Assisi, Orvieto

I don’t know where you have been already but if it were me I would perhaps visit parts of Tuscany but focus on Umbria and end up in Rome for your flight to Paris.

To me it looks like you have two options. Option one is after five nights in Florence is to travel south through to Rome seeing Orvieto and Rome and flying out of Rome to Paris

Option two is to travel north to Milan and fly out of Milan to Paris. You could add in Cinque Terre or even Lake Garda on the way. I don’t think you have time for the bernina express however it’s something that I’m looking forward to do later in this year

Both options add more or less stays as you want

First sort out your departing city and work your way towards the city and your last five days. You can choose what towns do you want to see and what you don’t. Just make a choice on that departing city and once that’s done forget about the other option.

That’s my two cents.

I don’t see any real discussion of what your personal and your friend’s interests are? First timer? What are his expectations? Museums, art galleries, churches, coffee/food/wine, ancient buildings, countryside, etc. I would get that sorted out first with both of you writing out what you want to see and prioritize. Are you going to allow time to just sit on a piazza, drink coffee or a spritzer and watch the locals (and tourists)?
There are fast trains from Florence to Rome 90 minutes +/-. Florence to Lake Como / Varenna is over 4 hours (we will be doing Bologna to Varenna, Xfer in Milano in October). I would suggest making your way South slowly, stopping where you want on the way to Rome and then, after spending enough time in Rome take a fast train back to Florence. I now try to allow 2 nights in each place if I arrive after noon.
As an earlier responder said, get a calendar and layout your schedule with estimate departure times, arrival times etc. Just keep playing with options and schedules. Florence to Lucca is easy. Lucca to Cinque Terra a little more complicated, Cinque Terra to Rome also involves transfers but doable especially if you catch the fast train Florence to Rome.

How about continuing to Naples after Rome? Naples has flights to Paris. 2 nights there is tight, but why not?

Thanks all - we've decided to just head south and leave from Rome. Questions - would you rather spend 1-2 nights in Siena or Orvieto? We were going to do a day trip to Cortona from Florence, but see it's only 45 min by train from Orvieto. Getting a plan together!
We have seen all the major cities and some Tuscan towns. Our friend has not. We are foodies, wine, sights, and interesting quirky things about a town or city.

I'd spend extra nights in Orvieto. If it works with your schedule, I'd take a daytrip to Siena from Florence.

I agree with Marsie, but I'm still wondering, "what are your friends' must-sees"? Especially in Florence, if your friends want to see sights in Florence that you've already seen, they could stay in Florence while you take a day trip somewhere.

I think you and your friend need to set out expectations so you all enjoy the trip. For example, are you ok if you each do your own thing during today and meet up for dinner? Or does your friend want you to hang with them all day?

Do you want to have a rest day where you just meander and see what the day brings, whereas your friend wants to have a set plan?

We ask our friend constantly what he would like to see and he just tells us I don't care. I've never been so don't know what to expect.

Sheesh.

Marsle beat me to it: more than one night in Orvieto. There's plenty to see there, enough for at least one full day. I could happily spend 2 or 3 nights there.

I would still consider renting a car and visit places places of Tuscany, Umbria, Lazio you haven’t seen before. Orvieto may be one, but the choices are endless and I don’t know where you have been already. In Umbria there is, besides Orvieto, Assisi, Spello, Spoleto, Todi. In Tuscany there is the Val D’Elsa (San Gimignano, Monteriggioni, Barberino V.E., Colle V.E., etc.), Chianti Area, the Val D’Orcia (Montepulciano, Pienza, Montalcino, San Quirico, Buonconvento), Maremma (Pitigliano, Montemerano, Massa Marittima, Saturnia, Argentario Peninsula, Capalbio, just to name a few). In Lazio there is of course Civita, Tarquinia, and more.
Florence car rental agencies are all in a street near the US Consulate called Borgo Ognissanti. Their cars are all stored at the multistory Interpark Garage Europa on the same street. I’ve provided instructions on how to get to the freeway from there (see my last reply in the thread below).
https://community.ricksteves.com/travel-forum/italy/car-rental-in-florence-airport-vs-train-station

In Rome all agencies have multiple offices. Where to return will be determined by the car rental company you rent from.
The locations at the Tiburtina station are the easiest to reach from the freeway using the Tangenziale est A24.
The Termini station location is also not much farther away using the same route. All Termini returns are at the multistory Giolitti parking garage.linked below. I return it there when I stay in the city of Rome. However if you will be in Rome just the night before your flight to Paris, you might as well stay at the Airport Hilton and return the car at the airport, walking distance from the Hilton using the aerial walkway. That is what I do when I return it the night before my flight home.

Interparking Italia Srl - ES Park Giolitti Roma Termini
06 4470 4053
https://maps.app.goo.gl/qjjcdAwpezzN51fW6?g_st=ic

JR - I have gone to Italy many times with many different people who were visiting for the first time, and that is not an uncommon attitude. It has been the rare person who said something like, “No, I’m not interested in museums or art, so I don’t want to go to Rome”, for example.
So, I have planned itineraries based on what I think they should see for their first trip to Italy, taking into consideration their interests, or lack of, and also included places that I want to either return to or see for the first time. Nobody’s complained, to my face anyway, about the trip they had. In fact, I think most people are just really excited to go there and get a glimpse of what it’s all about. And if they want to see more they can go back on their own.

I would recommend sending your friends to Venice by train from Florence for one night after you have been there a few days. It would give them a chance to experience Venice, and it would give you a day and a half to go see something you’re wanting to do. I think it would be a good break to then be heading south together as you’ve planned.

He only mentioned one friend, and sending someone off to Venice who is a “first timer” alone, doesn’t sound very considerate.

We did a 22-day trip through Europe last year, bringing along my sister for her first European vacation. My wife & I felt it was important to hit must-see cities but add in things that were new to us as well. It required a balance along with prioritizing what repeat visits would still entertain us along with new spots that we hoped would not bore my sister. We were luvky in that a mixture of the familiar and new made for a pleasant journey all around. In a nutshell, don't stress over it too much.

JR, when you ask your friend what they want to do/see, and they simply shrug and don't give a meaningful answer, that would worry me. I would suggest you have a more extended discussion about their interests and expectations, since the "I don't know I don't care" answer may mask some things that may surface later, once the trip has begun (I'd also ask myself questions about my own motives, tolerance for different travel choices, and compatibility). If nothing else, you should try to come to some clear understanding and a verbal agreement about shared understanding, boundaries and expectations.

Are you going to be there for them every hour of every day on the trip? Are they going to just follow along no matter what you choose to do? How is that all going to work (both for you and for them)? Will they spend any time apart from you? Will they learn any skills and gain experience from this trip, or just be a passive observer?

It may seem trivial now, but foreign travel can sometimes intensify issues in any relationship (especially true for those who have never traveled internationally)...some say international travel is a good "stress test" of any couple's relationship (who among us has not had that experience even with a spouse or other loved one?). Best to have these things discussed openly now, at home, in a relaxed and familiar environment, rather than when stressed about making a decision under less favorable conditions. Just a suggestion...

David: A very good suggestion indeed! You are right on with what can happen (especially with people who haven’t traveled overseas before).
Expectations definitely need to be discussed in advance. Also, time should be planned to be separate, even if only for short periods of time.

David makes a good point. My wife took one of her high school friends with us to Italy years ago (her first time in Europe) and after the trip my wife said never again. But that of course depended on the friend’s attitude and the type of relationship you have with him/her/them. In that occasion I was the one at the wheel. Not only because I was the driver but because I decided where to go when to go and for how long. The ladies (including my sister in law) called it the Mussolini tour but that’s the way it is. I drive so I make the rules. I am pretty sure your friend will enjoy the trip wherever you take him/her:them

Following up on another comment with a personal experience. I got married in Den Haag, Netherlands and my parents and another couple who were very good friends of my parents were coming over from Australia for my wedding. About 3 or 4 days before the wedding, my parents turned up at my future in-laws just fine. Next day the wife of the other couple turned up, missing her husband. They had travelled in a camper van around UK and brought it over to Europe and 2 or 3 days later, the husband and van had vanished while wife was in town. No message. Phone calls to her children in Australia but they had no info. Tried to get info about the camper van and no luck. Then the day before my wedding, she got a phone call at my in-laws place from her son: her husband was back in Australia. He couldn’t deal with the strange country, food, language, driving on the wrong side of the road etc so just panicked and flew home. He was educated, ran a successful small business in a small town and the strangeness just overwhelmed him.

This was an extreme case but I would be very concerned if your friend doesn’t express any opinion of what he would like to do or see.

I think that if you know this person well enough you don’t need to be that concerned if he doesn’t express strong desires to see one thing or the other, but can plan an itinerary out of what you think he would like. There really isn’t that much to choose from; beaches or lakes/mountains, medieval hill towns, islands, historic places/museums/art/churches, and then the cities that are hard for some people - Venice and Naples!

Thank you everyone so much for your input. It has been invaluable. Since we are 5-nights in an apartment in Florence at the beginning of the trip, my travel partner will do a day trip to Venice with him. I would rather stay in Florence and shop! We will do some day trips, i.e. Lucca, and not sure where else at the moment. We are thinking 1 night in Siena (should we?) the two nights in Orvieto, two in Rome, then fly to Paris. I have ready all your comments, and you all have great info and support. It will be a test of friendships for sure! The newbie is more a friend of my partner than mine, as I really don't know him well. They should at least have some fun! I think he is pretty easy going, and willing to go with the flow, but we still feel a responsibility to show him the highlights. I am not sure two nights in laid back Orvieto will be his thing, but, we will figure it out. Roberto, as always...........thanks!

Thanks again everyone!!!!!