Beginning Italy itinerary planning Questions

With two weeks, your three cities are about it. You might slip something else but those three will fully occupy your time. Keep in mind when you change locations you lose most of that day. Fly into Venice and come home from Rome. Best options. IMO it always makes sense to go "open Jaw" or multi-city. It is generally cheaper and more convenient. It is rare for us not to go open jaw. A car for those cities would be excessive baggage. That will get your start. When you return you can see some of the other sites.

And same to you, G. Italy's 20 regions are diverse and both urban and rural areas of each maintain fantastico history, traditions, art, architecture, music, culture, food, wine ... Read beyond RS guide book and seek out information on an area of Italy that speaks to you. If you want to take in a mostly city-focused jaunt, do expect crowds, be prepared for weather and appreciate the local environs to the fullest. Check out information on Sept/Oct festivals, harvest, events that have been happening for centuries and allow that to be part of your decision making. Hope you have as much fun planning and plotting your first Italy trip as you do having the experiences you enjoy along the way.

We just did 20 days in Italy, and did only Florence of the 3. Many of the smaller towns are more interesting to us. We went to Siena, Milan, Turin, Ravenna, Padua, and Pisa.

We really enjoyed Siena, as it is a quirky place with these neighborhoods which all compete against each other. We had a great Florentine steak there. We went to a chapel, and the priest invited us for evening mass. We were the only people there. He gave helpful commentary about the mass, since I told him we were not Catholic. A moving and thoughtful experience.

Assuming you have about 14 nights on the ground in Italy here are minimum recommend stays:
Venice 3
Florence 3- add 1 night for each day trip- Siena is easy from Florence
Rome- 4

Easier to fly IN to Venice than out of and it's a great place to get over jet lag.

I’d do something like this:

Venice 3
Florence 4- day trip Siena
Orvieto 2- beautiful Umbrian hill town, easy to get to, nice break between all the major cities.
Rome 5- could visit Ostia Antica in place of Pompeii

All easily done by train.

Looking at 2 weeks in either Sept or Oct. '23. Is one preferable to the other?

No!
Check airfare flying into and out of Venice and Rome (multi-city). If you fly home from Venice, make sure it’s not an early flight to avoid a hefty water taxi fee that will cost over $100. Buses begin running from Piazzale Roma near the train station as early as 4:20a. If you take the bus to Marco Polo airport (VCE) you need to stay within walking distance of Piazzale Roma because parts of Venice can be a bit scarry when tourists are sleeping.
You need a minimum of three nights in Venice, four nights in Florence with a day trip to Siena by direct bus (1h 15m) and four nights in Rome and that includes Vatican City. Naples is also an easy day trip from Rome’s Termini station to Napoli Centrale (1h 15m by direct train) but you need to add a night.

Happy New Year! We love traveling to Italy. I agree with Teresa’s advice. The weather in September and October will be good and the crowds smaller. We were there in mid Oct to early Nov this year, and the temperature mostly varied from 45-70 degrees in Umbria/Tuscany, unseasonably warm, but I had my raincoat for the few cool rainy days.

If you are focusing on Rome, Florence and Venice, you can easily travel by train. Prepare by watching videos and reading ahead, but also be aware that people will help you find your way. Rome is the most intense train station, especially upon arrival from the airport. We’ve only flown round trip, but I agree with the commenter who advised the multi city approach. My Italian friend regularly uses all the smaller airports, like Perugia and Florence, for her convenience.

Like another commenter, we love the hill towns. I think you could go to Orvieto by train, it would be a stop between Rome and Florence. It is worth seeing a smaller town to get the sense of a different region, food, and of course, a smaller town. Umbrian food, wine, and hospitality should not be missed!

I am also planning a two week trip to Italy 9/20-10/6/23, just over two weeks. I was planning to fly into Rome and out of Venice, but it sounds like maybe I should reverse this plan? Is it easier to get to Venice from airport that out of Venice? We are also hoping to include a stay at an agriturismo for 2-3 nights. Does anyone have recommendations for that? Is it best to rent a car near Florence and drive to agriturismo then return car and take train to Rome? Or rent car near Florence, travel through Tuscany or hill country and continue driving to Rome to return car? I was also wondering if it is realistic to add in a little time in Cinque Terre, or is that too many places for time frame. We have been to Italy once before and are traveling this trip with another couple who have never been, so we definitely want to go to Venice, Florence and Rome. Thank you for any tips.

jores-

Yes it is easier to fly IN to Venice than out of.

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parts of Venice can be a bit scary when tourists are sleeping.

U serious? Venice is one of the safest cities in Europe.

Tourists can sleep as long as they like, you need locals to avoid getting lost when it's dark.

parts of Venice can be a bit scary when tourists are sleeping.

It is when you encounter a group of guys who stopped talking and watched me as I passed by. I was alone and nervous as I made my way back to my room. When tourists return to their hotels you should too.

TY all who responded with great info to consider as I plan. Much appreciated.