Cinque Terre to Siena Advice (transport and/or side trip ideas)

If you decide to go by train, enter Monterosso (or any other village in the Cinque Terre) and Siena on trenitalia.com/en.html .

The September 2023 schedules will be fully uploaded on June 12, 2023. Use a day of travel before December 11 to get an idea of the current summer schedules.

Click search and the site will show train type and code, departure and arrival hours, total travel time, the number of changes and the cheapest available fare (per group).

Click on the number of changes to see where and when you'll have to transfer. There are no reserved seats on R and RV trains, in short the Regionales can't sell out.

You'll have to take the train to Pisa and change to another train that goes to Florence--getting off at Empoli. You pickup another train in Empoli that takes you into Siena. It's a 4.5 to 5 hour trip.

The train station in Siena is on the outskirts of town so you might have to take a taxi to your hotel from there.

How about going from Venice to Monterosso, then Florence, then Siena?
Venice is a long segment on a train, but if you take via Milan, there is the possibility of getting to Monterosso with just one train change (at Milano Centrale) and both segments would be on fast trains (a Frecciarossa to Milan, and an Intercity from Milan to Monterosso).
Monterosso to Siena is a long trip primarily because of the many train changes (potentially at La Spezia, Pisa, Empoli). Going from Florence to Siena is a breeze.

Yes, I totally agree with Roberto. We did this same journey, Venice to Monterossa, but in the opposite direction a few years ago when we were new to train travel in Italy. It was very simple, one change in Milan. It takes a while, but we enjoy traveling by train and look at is as part of our sightseeing adventures. By going to Florence after Cinque Terre you are alternating your larger cities with smaller towns. Whatever you do you will love Italy. I am planning our fourth trip right now for Fall 2023!

Thank you for your recommendations (sorry, I do not know how to reply to individual responses!). Yes, I am using the Trenitalia website for my travel plans. I did look at going to Cinque Terre after Venice, but thought I saw the train from Venice to Milan was 6 hours. When I saw I could get from Florence to La Spezia Centrale in under three hours (couldn't figure out how to get to Monterossa from La Spezia but was going to ask our hosts when we made our Monterossa accommodations), I chose my sequence of cities/towns. Maybe I didn't find the "fast train" option and/or wrong start/stop location names? FYI will send out another forum question asking for help with exact wording I need, based on where we are staying at each city/town, to find my transportation options.

Also, I don't think I was very clear when I asked if we should stop in Pisa, San Gimignano, and/or Volterra on our way to Siena. I meant: do I add any of those sites as "touring" stops on our way to Siena or would it complicate my travels even more (which, again, I'd rather keep the "easy button" option, so if it complicates things, I'd rather not do).

I don’t know if you can make changes to your plans, but I would do Venice>Monterosso>Florence>Siena>Rome.

To go from Venice to Monterosso I would go via Milan. Using Trenitalia you can find all the solutions but most send you via Florence which is generally a bit faster but requires multiple train changes.
But you can also go via Milan with a high speed Frecciargento 9794 departing Venezia Santa Lucia station at 10:48am. The train arrives at Milano Centrale at 1:15pm, where you have 50 min (plenty of time) to change trains and take the Intercity 669 which arrives at Monterosso at 5:05pm. It is a 6h 15m journey in total, but it would be the most comfortable because you are on the fast trains and, above all, you need to change trains only once and with plenty of layover time.. Changing trains is a pain if you have luggage because you have to haul the bags yourself on and off trains.

From Monterosso to Florence there are many train options, many with one change only (either in La Spezia or Pisa) with a total travel time that ranges from 2.5 hours to 3h48min and everything in between.

From Florence to Siena you can take either a bus or a train. The bus is faster and also drops you inside the Siena city center which is on top of the hill. Trains don’t go on top of hills so the Siena train station is located down the hill outside the city center. From the station you will definitely need a taxi if you have luggage.

Regarding visiting San Gimignano and/or Volterra that is not a convenient option to do while you are en route to Siena because you will probably be encumbered by your luggage and there are no viable luggage storage options at smaller stations. The best option to visit San Gimignano is with a day trip from Siena after you have checked in the hotel and therefore you are free of luggage. If you have booked a private tour of Tuscany from Siena, I bet San Gimignano is part of that tour, being the most visited town in the Siena Province. Volterra is too much trouble from anywhere if you don’t have a car, but maybe your private tour includes that too.

Roberto, you are so helpful! Help me understand what I am seeing on the Trenitalia site. Venezia S. Lucia (departure) and Firenze S. M. Novella is 2 hours 13 minutes via Frecciarossa 1000 #9431 (I used Dec 18 travel date to get an idea of offerings) .... details show me a bunch of stops, but I don't see that we change trains. We'd spend 3 nights in Florence. Then I used a Dec 27 travel date from Firenze SMN to Monterosso and found R+R at 3 hours 45 minutes (it looks like Regionale 18361 to La Spezia Centrale with a 55 minute layover and then a 23 minute ride via Regionale 12228 to Monterosso. Isn't this better than a 6 hour train from Venice - Milan - Monterosso? Again, I am a novice at this Trenitalia stuff, so I may not be entering info in correctly. Please advise!!!

If you want to go to Florence after Venice, then yes, that is the way to do it.
From Monterosso to Siena use the same website, enter from Monterosso to Siena.