Itinerary help Rome to Venice late September/early october

Welcome!

You could head to Orvieto on arrival- stay a night or 2-worth it- then pick up car there- Hertz will be your only option and AutoEurope probably not an option for that location anymore but check their eu site
https://www.autoeurope.eu

From Orvieto head to Siena- that's a nice drive and will take you thru Val D'Orcia.
Much easier to have a car in Siena than in Florence-where you will not want or need a car.
Stay in Siena and day trip to Florence maybe. Depends on what you want to see/do but you will only need the car for exploring Tuscany hill towns. I wouldn't split those 3 nights- too much moving around.

Then to CT- 2 nights. I'll let others address that segment.
Train to Venice 2 nights

Orvieto 1
Siena or Florence 3- again no need for car here
CT 2
Venice 2

Or you could do
Orvieto 1 or 2 nights
get car
Siena 1 or 2 nights
Drive to La Spezia- drop car
CT 2
Florence 3

Or you could skip the car entirely
Orvieto 1 night
train to Florence 3 nights- day trip to Siena
CT 2 nights
Venice 2 nights- takes most of day to get there

You'll have to go thru Florence to get to Venice from CT

Note spelling of locations- you will need correct Italian spelling and station names when searching for trains, etc

If you do rent car- all drivers must have an IDP-International Driving Permit- get at your local AA
Do your homework regarding driving in Italy- ZTLs, speed cameras, parking, etc

Trains
Trenitalia- fast trains and regional trains
Also has easy to use app
https://www.trenitalia.com/content/tcom/en.html

Station names
Roma Termini
Orvieto
Siena
Firenze SM Novella
Monterosso
Venezia Santa Lucia

Venice needs a minimum of three nights.
Condense your stay in Tuscany or Umbria to one location and do day trips if desired. If it were me, I’d base in Siena. Orvieto can easily be done as a day trip.
Cinque Terre- Monterosso gives you the most options for everything in . There is a large parking lot if you decide to have a car.
Or skip the Cinque Terre and add that time to Tuscany. You have too many places and too little time for them.

I haven't traveled by train from CT to Venice, but did train in Italy before cruising from Venice. We arrived Milan, took train to Lake Como (Varenna) and then train to Venice. The train and cruise terminals are relatively close to each other and not close at all to St. Mark's Square, for reference. This year we are cruising from Athens TO Venice then train to Lake Garda, Lake Como and home from Milan. It's easy to get into and out of Venice by train.

It has been a long time since I went to CT, and I had a car.

I wouldn't stay overnight in Siena, but it's a good stop. Orvieto is also a good stop.

"Touring" from Rome airport is not easy or close to anything. I would stay there for a couple days and then train the rest of the way.

Hi, one other comment before you reserve hotel rooms at Venice. Check to see exactly where your cruise leaves. It’s common now for cruise ships to say Venice/Ravenna when the ship is actually leaving from the port of Ravenna which is 90 miles south of Venice.

Is your ship actually leaving from Venice or from some other port such as Ravenna? Most cruise ships are now banned from Venice. If you are leaving from Ravenna it is worth a stop to visit the early Christian mosaics. As Ravenna is quite a distance from Venice I would skip CT and spend those days in Venice, then head to Ravenna the day before your cruise leaves. As your friends are planning on going to Sorrento they will have the chance of seeing stunning sea views on the Amalfi coast.

Thank you for the great information! I am excited to get things booked.

Based on these comments, I am rethinking the time in Cinque Terre. If we do include it, will it make more sense to go from Sienna to CT, then CT to Florence then Venice?

I am interested to know if anyone has done the hill towns with public transport vs car. Not excited about driving in Italy and would only consider having a car in the countryside, not cities.

Our cruise leaves from Fusina, but the cruise line will pick us up from the Stazione Marittina.

Lastly: Would love to hear of any recommendations for cooking demos/classes and olive oil production.

Thank you again!!!!

Arrive Rome early, stay 1 night Almost thinking of stashing bags at train station, tour a little, then catch a train out.

From Rome (Roma) Termini there’s a direct train (no connections required) departing at 6:15p to Orvieto (1h 6m) where you’ll need to get off at the second stop arriving in Orvieto at 7:21p. Riding the rail is when you’ll most likely doze off so I recommend taking the fastest train which is this one. To get to the top of the town ride the funicular outside the station and sleep in Orvieto a minimum of two nights: https://en.wikivoyage.org/wiki/Orvieto. Orvieto will be a wonderful stop to help cope with jet lag.

Should we spend all 3 nights in 1 place?

Italy is approximately the same size as California and you’re talking about visiting two regions within two days. Are you sightseeing in Florence or using it as a base to visit Chianti? I don’t know how long it takes to drive from Orvieto to the Chiantigiana Road (the road that runs between Florence and Siena in Chianti), but it takes 1h 45m and that does not include stops.

Florence deserves a minimum of three nights. You can take a direct train from Orvieto to Florence SM Novella station (2h 30m). You can then rent a car in Florence (read up on ZTL laws before doing this. Driving in a bus lane for a few seconds is costly) and visit Chianti by driving along the Chiantigiana Road and drop it off in Siena.

I’ve read it’s not a good idea to leave luggage in your car no matter where you are in IT. I’ve left mine in the car in Tuscany and had no problem.

Skip the Cinque Terre that's more convenient from Milan. It’s an outlier from Orvieto and Florence. There are no direct trains from Monterosso to Venice’s Santa Lucia station which is the end of line and where the lagoon is. Furthermore, you need three nights in Venice.