How do you create or narrow down an Italian itinerary?

I would say the first determining factor is how many days? Followed by what month of the year?

I make a list, in order of of importance to me. Then i give each place 3 nights minimum. When i run out of vacation days, that’s the end of the itinerary. For me, there is no point in going somewhere if i don’t have a minimum of two full days there. ie, 3 nights.

If there are day trips i want to do from a base, i add that day to the amount of full days i stay at that base.

All bets are off for Paris though, i need minimum of 2 wks there, and even that is too short, lol.

The RS book will have suggested itineraries in it. You could also look at the itineraries of group tours, RS, or others, and kind of emulate those. (Note that you'd have to slow down any group itinerary. Independant travel doesn't benefit from some of the efficiencies of being in a group.

I hate to break it to you, but there are lots of interesting destinations in Italy Rick doesn't cover because the publisher has told him he cannot add any more pages to the book! Even when you've been to every place in the book, you have more work to do. And there's an entire separate book for Sicily!

I don't plan trips to entire countries when the countries are sight-rich like Italy. I just try to cover some regions, ideally regions that aren't too far apart. Any given trip might include my priorities 1, 3, 5 and 6 because that grouping makes sense geographically. That saves time (so I can see more) and money. If I have less transportation expense, maybe I can afford to stay an extra day or two.

Last fall I wanted to attend a special event in Venice (where I hadn't been for 30 years), so I added on 3 nights in Padua and 3 nights in Ravenna. I had been to the latter two in 2015 but had felt rushed.

I decided this winter I could go to Rome and see a lot of the indoor sights even if the weather wasn't great. (It was generally fine except for the easy-to-anticipate short days.) So I added a week in Naples (day tripping to Pompeii and Herculaneum) and four nights in Salerno (day tripping to Paestum and Eboli). Because I wasn't traveling very far, I took less expensive (and slightly slower) InterCity trains rather than Freccia trains between Rome and Naples.

I will probably return to Venice in 2024 and will venture to a bunch of other interesting places in northeastern Italy like Treviso, Udine and Aquileia.

The Dolomites are lovely. There are some very nice cities and towns in the valley through which the rail line runs (Bolzano, Bressanone, Chiusa), and nearby Merano sounds worthwhile. You'd probably pass through Verona on the way to the mountains. Then you have Vicenza, Padua and Venice right on the rail line heading east from Verona. In the other direction you have Milan and--on a secondary rail line--Bergamo.

I have been trying to get to Turin for a long time but haven't made it yet. I try very hard to focus on what it's practical to see on each trip rather than on what is being postponed.

Good advice from everyone. But basically anywhere I can go in Europe will cause me to make decisions about the specific locations. So it’s not unique to Italy.

My philosophy may not be the same as yours. I would rather spend more time within a certain region (or country, depending upon size) than hit the big cities in several different countries or regions. But other people like to spend more time in cities than smaller towns. Some people like to stay in the same lodging and take day trips - others like to keep moving in a straight line.

There is no shortcut for your own research except signing on for a tour and going where someone else has decided. Neither way is wrong.

We start by focusing on an area of interest, often booking a small-group hiking tour, and then add towns or cities that appeal to us. They may be near the main destination, or on the way to or from. We like to mix familiar favorites with new places.

For example, our last two trips to Italy were in September 2022 and March 2023. The first was build around 10:days of hiking in the Dolomites with a small group, booked with a wonderful little company that did all the planning, booking, and guiding. Then we added a week on the front end to make our way to the Dolomites to meet the group. We visited Luzern, Milan, Lago di Garda (Desenzano) and Verona, in that order. Then we spent week in Bologna after the Dolomites, with a flight out of Venice.

Our March trip was focused on Puglia in the south. We flew into Rome and made our way by train to Lecce to meet our group. After 11 days in Puglia, we made our way north by train, with overnights in Bari and Rimini (a surprisingly pleasant find) before our longer stays in Ferrara, Venice, and Bologna. We flew out of Bologna, a nice small and easily-managed airport.

We have been to Italy on 5 previous visits, with long stays of a week to a month in the Dolomites, Rome, and Venice, and shorter stays in Cinque Terre, Lucca, Milan, Verona, Florence and Siena. Now we are focusing more on areas to hike, and places a bit off the beaten path.

Speaking of the Dolomites, you might get this excellent guidebook rather than rely wholly on Rick’s book. It will be money well spent if you want to have a good visit. September is a great time to visit—-we will be back there ourselves then. I wouldn’t go later than mid-October, however. So it might be best to start your fall trip with the Dolomites, and extend from there.

https://www.amazon.com/Walking-Italys-Val-Gardena-Dolomites/dp/B0BT6RHGKV/ref=asc_df_B0BT6RHGKV/?tag=hyprod-20&linkCode=df0&hvadid=647178177741&hvpos=&hvnetw=g&hvrand=16752113515387043075&hvpone=&hvptwo=&hvqmt=&hvdev=c&hvdvcmdl=&hvlocint=&hvlocphy=9033255&hvtargid=pla-2012011498767&psc=1&gclid=CjwKCAjw8-OhBhB5EiwADyoY1aRtDf2Cr_UQFOciq58cL9z0wLcA9Yth4X1uJmUv00RP5uS89hSWsBoCQrUQAvD_BwE

My approach to trip planning is very time intensive, and it sounds like that isn’t what you’re wanting to do. So, possibly it would help to just browse through some of the traveler’s fantastic scrapbooks that they submitted to visually see which cities and activities appeal to you. I saw some from these tours: Heart of Italy, Village Italy, My Way Italy, Best of Venice/Florence/Rome

https://www.ricksteves.com/tours/scrapbooks

Why don't you review the Trip Reports here on the Forum,
watch the RS videos ( from library or PBS),
watch Stanley Tucci's shows Searching for Italy on Italian food,
and maybe Eugene Levy's the Reluctant Traveller, episode 3.

You need to define your interests and travel style. Perhaps all north or all south itinerary. What's a priority for you?
Good luck!

When I plan my itinerary I will divide the country in north ,south ,east or west and just focus on those areas , that usually requires multiple trips to that country. In the case of Italy 🇮🇹 I will do north,central
and south and later on Sicily .Or do everyone favorite Rome ,Florence and Venice .
Have fun ,enjoy you planning.

What are your interests? History? Art? Food and wine? Scenery?

Rick Steve actually has a good You Tube video on this very subject and I follow it for each trip.
Search: Rick Steves European Travel Skills: Planning Your Itinerary

On lined paper I write down everything I want to see/do separated by Location (Rome, Florence, Amalfi, Paris, London) and a line item for each thing...so I land up with a huge list

Then I do a top 10 for each place

Then I take a lined piece of paper and number each one for the days I am on the ground then start plugging in my top 5 for each place, so If I am in Rome for 3 days and I have 10 things I want to do...now I start prioritizing and 3 things will be my "A" list and the rest goes on my "B" list, so if we have time we may get around to doing those things OR maybe I actually need 5 days in Rome now.
Same with Paris, I have 10 things but only 5 days, 5 will be on my "A" list..and the rest on the "B" list., Oh but I need to steal 2 days from someplace to make my Rome dreams happen...Then I see that the more I move around the more days I lose for what I want to see/do so then something has to go.

It's a puzzle that I love figuring out.

Thanks for the advice! I realized most of our interest is in the southern part of Italy so we'll skip the Dolomites on this trip. I'll use a new thread for further questions.