2 weeks in Tuscany

The one thing I wouldn't do is drag my luggage to Siena for just one night. For that little time in Siena, I'd opt to make it a day-trip from Florence. The usual recommendation is to take the bus, which I believe takes about 90 minute for several of the departures. But you may well want more time than that in Siena--or perhaps you especially want to be there in the evening.

Looks like a lot of backtracking.

Where will you be before getting to Florence and where are you going after CT?

Have you plotted your path on a map?

I see from your other post this is still a 'work in progress'. Try to avoid your travel path looking like a seismograph tracing during a 6.0 quake

I would probably take an evening train to Pisa and sleep there instead of Lucca because you have a lot going on the day you pick up your car. Here's the order I would drive to the places that you're wanting to see from Pisa:
Certaldo (1h 15m)
Voltera (45m)
San Gimignano (45m)
Siena (1h)
Montepulciano (45m)
Pienza (20m)
San Quirico d’Orica (15m)
Montalcino (15m)
I have never been to Certaldo so I don’t know how much time is needed there. It sounds like you don’t want to do a lot of one-nighters so you’re trying to decide on three places max on where to stay.
I have stayed in Volterra and recommend it. San Gimignano makes a nice day trip but I wouldn’t sleep there since it’s quite small and you don’t need a lot of time there. Siena is a wonderful place to visit, but I wouldn’t want to drive more than two hours to visit places from where I was staying. It can also be tricky getting in and out of there when driving.
I would also consider sleeping in Montepulciano which I also loved. You get more out of a place when you spend the night.
If there’s a place I would skip it’s Montalcino because there’s not much to it. I believe you have to know a lot about wine to fully appreciate it.
I would probably spend one night in Certaldo because it would be a long day if you didn’t. The next day drive to Volterra and spend one night. From there I would have lunch in San Gimignano on my way to Siena and stay there two nights before moving on to Montepulciano. I would then take day trips to Pienza, San Quirico d’Orica and Montalcino.

Thank you, we are travelling from T.O. to Venice (4 nights). From Venice to Florence (4 nights), then after Tuscany countryside (around 9 nights), CT (2 nights), Rome for most of a week (remaining time), and back to T.O. Total of about 1 month (need almost a week in Rome due to plans). I hear you about luggage, as it sounds like Siena will be busy.

To lessen the running around and backtracking, I am now wondering if we would be better off to Go to Lucca as a day trip from Florence (stay 5 nights instead of 4 to provide 3 full days in Florence), then pick up a car at the Florence airport (better than city central), and get an apartment in one of villages (i.e. Volterra). We could stay a few nights and do day trips from that area, then leave early morning for Siena to spend the day and one night and following morning in Siena (leave car outside city, small bag to hotel), on our way through to San Quirco area. Spend 3 nights prior to returning car to Florence airport, and take the train to CT.

Does this sound better?

just JYI - we did 2 amazing day trips from Florence into Tuscany with WalkAboutFlorence - check out their website - we LOVED their BEST of TUSCANY TOUR (which goes to Pisa, we didn't find Pisa needed much time at all), Siena, and SanGimignano. We also loved their CHIANTI WINE & FOOD SAFARI TOUR. Venice and Florence are 2 of our most favorite cities in all of Europe!!

In 2019, we rented a car and headed to Tuscany after three nights in Florence. We spent three nights in Volterra, from where we did a day trip to San Gimignano. Then we picked up friends at Siena train station and headed towards Montepulciano. We stopped in San Quirico on the way for lunch, then spent three nights in Montepulciano, from where we did day trips to Pienza and Cortona. Then we dropped off car and spent one night in Orvieto before taking train to Rome, from where we flew home two days later. Was a great trip.

I would either do Siena as a day trip from Florence (we have done this by bus many times) or once in Tuscany drive in for a day (the historic center is ringed with parking garages)

We spent two weeks in Montepulciano at an apartment with parking about 9 years ago and used it as a base. It is a bit far to Volterra -- we had friends who had a 500 year old estate near Volterra and we drove there for lunch one day --- I might choose instead if I were you to spend 3 nights in Volterra and visit SG and other sites from there and then have a place in the Val d'Orcia -- Montepulciano is great -- there are other spots.
The view from our balcony in Montepulciano is at the end of this photo journal:
https://janettravels.wordpress.com/2011/09/20/patterns/
Uprooting and moving is a drag -- I'd get situated and then use that area as a base.

How lucky you are to have a month in Italy!
I am assuming this is your first visit?
Exactly how many nights do you have on the ground in Italy? You say a month so I will assume 28-29 nights?

We’ve visited most of the locations you have planned- other than CT- and plan to return to Tuscany again in 2022.

First- there is no need to get your car at the airport- it will cost more and is out of the way. You can pick up car as you leave Florence from one of the city center locations- we picked up at Hertz Sansovino, the other is Borgo Ognissanti near SMN train station. We always use AutoEurope for our rentals. Be sure you read all you can find about driving in Italy- ZTLs, parking etc. All drivers will need an IDP- International Driving Permit- you can get at your local AAA for a small fee.
Do some searches here on forum for “renting car in Florence”, “driving in Tuscany”- there is tons of really important info especially on how to navigate out of Florence. It was much easier than I expected.

I would try to cut out 1 and 2 night stays. Where you have slotted CT in your plans doesn’t make a lot of sense to me and if I was going all the way to CT I would stay 3 nights- your arrival to CT day will be mostly spent getting there, especially if you are coming from San Quirico area. Then from CT to Rome is a long haul.
Pisa only needs a few hours, I wouldn’t spend a night there.
I see nothing wrong with splitting your Tuscany stay between 2-3 locations. We enjoyed Siena very much- stayed 2 nights and yes we drove- there are a couple really nice hotels with easy access parking (Palazzo Ravizza- fantastic terrace with views and just steps to Campo, another is Hotel Athena). I don’t think we would have liked Siena nearly as much if we had just day tripped. The evening was delightful. True that driving in to Siena was a bit dicey- but we managed. We didn’t do any day trips from Siena- just parked the car.

I’d try to simplify/shorten all of your transits.

Something like this:

Venice 4 nights
train to
CT- 3 nights
train to
Lucca 3 nights- day trip to Pisa
train to
Florence- 4 nights- this is only 1 hr 20 min trip so you could drop 1 night here, you’d still have almost 3 full days for Florence
Pick up car as you leave Florence

Now you are in Tuscany countryside- the choice of where to stay is yours.
You could do 2 nights Siena- no day trips
then move to
Volterra- 3 nights- day trip SG, Certaldo, etc
then move to
San Quirico area 3 nights- day trip Montepulciano, Pienza, Bagno Vignoni, etc
(We stayed in and LOVED Montepulciano but it’s also a pain to get in/out- next trip we are staying in Pienza)

Or pick 2 places and stay 4 nights in each. Or drop 1 night from Florence- pick 3 places in Tuscany for 3 nights each…
That is 22 nights so far.

Drop your car in Chiusi (30 min from Montepulciano) and take the train to Rome (2 hr ).

I like to use www.rome2rio.com to plot routes and get an idea of transit times and options.

Happy planning!

Thanks again to all. Looking at the routes and comments, other options would be Venice (4 nightsr, train to Florence (4 nights) (include a day trip to Lucca/Pisa from Florence). Rent a car in Florence, and drive directly to the South of Tuscany (i.e. Montepulciano area) - direct is about 1.5 hour drive. Stay 4 nights. Go to Siena first thing in the morning and stay in Siena 1 night, small bag and hotel in central part. (There are conflicting views - day trip/stay - I think we would like one evening in Siena). In the a.m. following day, visit Monteriggioni/lunch, then check into some place in North, i.e. Volterra and spend 4 nights prior to returning car to Florence. Take train to CT for 3 nights. Train to Rome for 1 week (need a week).

I did some checking, and Venice to CT would be 5.5 hours via train - too long. CT to Rome is 4 hours, which is manageable. Florence to CT is 2.25 hours, which is doable. I think if we start at the South end of Florence and work out way backward, it makes sense when leaving Florence for another destination. We can take the "fast" route to destination in the South, while, doing the backroads on the way back to the North to make some stops along the way. San Gimgnano, Certaldo, Chianti etc., can be done via day trips at the end of our Tuscan portion of the trip. Is this making sense?

Makes sense but look at dropping car in LaSpezia
As long as you have it might as well drive as far as you can towards CT and avoid going back into Florence.

Or return in Pisa at train station

I'd skip the one nighter in the hopes that you can come back one day and need not see everything on the wish list. In fact, I'd argue for two Tuscany stays (Florence plus just one other place) rather than three. But we all like a different pace of course, just giving you more to ponder!
Staying longer and heading to Rome after works better for CT, but I'd also consider skipping it in lieu of something else. Southern Tuscany has some wonderful places on the coast near Monte Argentario, with fantastic hiking in Maremma/Ucellina park. You could keep the car, ultimately dropping it before Rome. Just an idea--after Venice and Florence and prior to Rome, I would want some quiet. But it helps to know what you want out of CT.

See if this would work for you. It involves little backtracking.

Venice-Florence (T 2H05m). 3-4 N Florence.

Florence-Lucca ( T 1H20m). Luggage storage @ station. Visit Lucca.

Lucca-CT ..
Late afternoon train 1 1/2-2hours dependent on village. 1-2 N. village of choice.

CT-Pisa (1H10m) luggage storage @ station. Visit then...
Pick up car, head to Volterra (45m). 3-4 N Volterra.

Volterra- Siena, visiting Certaldo or Montereggioni on the way. 1-2 N Siena.

Siena-Montalcino 50m. Visit. Montalcino then drive to...
Pienza/San Quirico d'Oricia/Montepulciano using one of the three as your base for 3 N.

Drop car at the Chiusi rail station, train to Rome.

@mandmsully2

A long time ago when the earth was green, 2010 actually, my wife, her 2 brothers and I spent 5 days in western Tuscany, in September waiting for my 16-year-old daughter to finish a tour with her school group. Have spent time in eastern Tuscany and Umbria on other trips. Rather than make suggestions this is what my travel diary tells me we did. Maybe it will be useful to you. Or not.

Sun 26th Sept. After overnight stay left Orte and drove via autostrada to Pisa. Spent about 1 hour at the field of miracles. Can say I have been there, but that is about it. Brother -in-law picked up a ZTL, he deserved it. In hindsight should have taken time to walk along both sides of the Arno River. Leisurely drive via secondary backroads to San Gimignano whilst enjoying the olive groves and aroma of ripening grapes. Stopping a couple of km’s to the east of San Gimignano at Trattoria Borgo di Racciano for a slow lunch. The executive chef, and cooks let me into the kitchen to watch afternoon practice for the Singapore Grand Prix with them on the tv. Unsurprisingly they were all Ferrari fans. Had dinner at our agriturismo Villa Bacioli, about 4 km’s east from San Gimignano, (https://www.villabaciolo.com) on the terrace looking west over the autumn fields ready for harvest with the towers of the town in the background absorbing the orange sunset rays.

Our preference is to stay in the countryside rather than the cities. Enjoy driving through the countryside. Does not suit everybody but does for us. In my youth my Italian schoolmates taught me some rather basic and rough Italian. Enough to get by with. I find most people are friendly and helpful. Also helps not to take one’s self too seriously. Try not to compare with your normal surroundings. A little self-deprecation is immensely helpful. It may also be useful to brush up on navigating skills.

Mon 27th Sept. Breakfast on the terrace, included in fare. Morning in San Gimignano, my wife buying up presents for people back home. Lunch at La Stella with friends from Melbourne who were in the area. Drove to Siena in afternoon. Parked at 24-hour car park below Siena’s Cathedral. The paying machines were the same setup as at home. Cash or c/cards with pin. Took the escalators up to the Cathedral. A further 800 metres gets one to the Campo square, unless one takes a wrong turn. Wandered around for a few hours, ate at some unremarkable restaurant. Struck up a conversation with a bloke at the next table. Similar fields of work. Between his passable English and my rubbish Italian we had a good time. Purchased the obligatory gelato and left around 11pm.

Tues 28th Sept. Breakfast. Drove to Florence along secondary roads and parked at Piazzale Michelangelo. Took the red bus into the city centre. My wife went present shopping again and I reacquainted myself with the interior of the Duomo and surrounds. Took local bus up to Fiesole for afternoon tea and snack and the view. Met up with our friends again for pizza dinner on the other side of the Arno, Oltrarno, at a local pizzeria. Left around 11.30pm.

Wed 29th Sept. Breakfast. Into San Gimignano for more present shopping while I wandered the back streets and found an obscure church on the outskirts with an interesting fresco, mentioned in the Italy guidebook. Chatted with a priest type. Had time for a swim in the pool. To Volterra for the evening. Parked just outside main gate. Found La Vena di Vino Tavern as per Italy guidebook. Stayed for an hour or so tasting and discussing sangiovese and super Tuscan wines of the area with the hosts and comparing then with my local shiraz and cab sav. Purchased a couple of bottles for later. Not my night to drive so could booze up. Ate at Don Beta Restaurant inside the town. Enjoyable food and surrounds. Left about 11pm.

About midway between Volterra and San Gimignano passed a brightly lit compound. Later found that is one of Italy’s high security prisons where convicted mafia are usually incarcerated.

Thurs 30th Sept. Breakfast. A leisurely day driving around the chianti area looking for a supposedly named San Paulo market. Never found it. Get lost and see what transpires type of day. Stopped at various times to watch the grape and olive harvesting. Lunch in the main piazza at Grieve. A wander through Radda. Into Poggibonsi commercial district for my wife to buy shoes for the two daughters who stayed home. Driving around we noticed a local restaurant at Castello San Gimignano, Tri Archi. Tried it for dinner. Had no reservation, but they made room for us. Turned out to have an Italian only menu. Great dishes showcasing locally grown saffron. Drove to Venice next day.

Regards Ron