Siena: Advice on driving in and around its outskirts

Driving in rural Tuscany is easy, with some preparation. However, my first question would be if you plan to imbibe at the reception and if the couple has made any arrangements for transport. Maybe they have a wedding website where people can share arrangements. Share the location, too--there are some locals here who may know the likelihood or ease of ride share. It may be that it is something that you need to arrange in advance.

Hello Valadelphia,

Thank you kindly for your responses and advice. I've posted the wedding venue location. The couple has not organized transport yet, but that is not a bad idea. If we go with a car rental, then we'll forego drinking on the day.

I love wine, so I would scope out the option for a driver either way. Your hotel could help arrange a private driver.
It's only about 20 minutes, so staying in Siena is an option if you want to be in town, or there are lots of rural stays in the area--some quite close.
I think I would decide overall based on how many days you will be in the area, how much exploring you wish to do, that kind of thing.

My husband certainly agrees with you on imbibing. We'll look into organizing a driver. We actually have a total of 21 days in Italy. We'll arrive August 24th - we haven't bought tickets yet - in either Rome or Venice then work our way over to Siena.

We'd like to visit:
Rome (4 days)
Florence (3 days)
Siena (2 days)
Assissi (1 day)
Venice (3 days)
Cinque Terra (2 days)
If time permits, we'd love to take a ride on the Bernina Express to St. Moritz

We're leaving 6 days to cover travel and flexibility to spend more time in places we like.

Would love to hear your thoughts on where we should start and where to end. Of note, we're flying to Africa after the 21 days so definitely need an international airport for departure.

Thanks for all the nuggets thus far!

I can't speak to the Switzerland foray--those routes confound me!
If you stick to Italy, I'd do a north to south route, starting in Venice and ending in Rome. I guess a lot depends on the wedding date and where you have to fit that in, but starting with Venice and Florence, then a little rural village downtime with the car, then finishing in Rome, sounds like a lovely trip. Assisi is a bit of an outlier, but you could add it in to a Tuscany-Umbria trip. Pick up car as you leave Florence and drop on arrival in Rome.
For only two nights in Siena, it may not be worth it to have the car, but you could use those extra nights you currently have set aside to tool around Tuscany a bit.

Ah! Yes we are are confused by those routes, as well.

The wedding is on 28th so we definitely have to be in Siena on the 27th. That gives us 2.5 days to explore one of the major cities. We could start in Venice and travel down to Florence/Siena the morning of the 27th, but gives us little time to enjoy Venice properly.

We could arrive in Rome, head to Orvieto on the way to Siena, do the wedding and start making our way North via Florence.

Assissi is driven entirely by Rick Steves' segment on it - we've watched it so many times! If another "off the beaten path" location is worth exploring, please let us know!

We plan to use trains for most of our trip and would only rent a car for the wedding events.

We are retired and so have the luxury of prolonged stays in places. But, I think you are traveling too much and spending too much time doing it. Check with Rome2Rio.com for travel times between your stays. I am assuming you want to visit some of Italy's world class museums and churches. I would drop Assisi and CT, adding those days to Venice ( or Rome), Florence and Sienna. I agree that it may be better to start in Venice (Marco Polo Airport). Then train to Florence. Maybe a day trip from there by train to Pisa. Bus to Siena (bus is quick & cheap and leaves you in Siena town). Arrange for a car & driver for the wedding - imbibe as desired. Take a train to Rome Termini station. When leaving, return to Termini (buses and taxis easy to get) and take the Leonardo Express train to FCO airport. No need for driving and no stress from Italian drivers trying out for a race team or trying to find parking. Enjoy Italy.

On driving in Tuscany, it is relatively easy to drive, especially in Chianti region. The big challenge, specifically in Siena is parking. If you stay in Siena, you can arrange transport to the wedding and then hire a guide or go on tours to take you wine tasting. For us, we had a group and someone needed to be the designated driver and didn’t drink.

Thank you all for the sound advice. It is good to know that arranging a driver for the wedding will not be a challenge. Please share any suggested car transport companies you'd recommend. I'll have a look through other posts as well.

Definitely taking the advice to spend longer periods in each of the cities. We arrive on August 24 and the wedding events are on August 27 and 28th. As a result, we will only have two exploring days at a port of entry. We're worried about giving Venice only two full days or splitting a longer period of stay on either side of the wedding dates.

Would you suggest, we split up our time in Rome? Spend the 25 and 26th seeing some things. Siena: 27-29. Then Florence for 4-5 days (day trip to Pisa) and onwards to Venice? Then return to Rome for additional days at the end of the trip?

Or should we land in Rome, and go straight to Florence, use those first two days to explore, Siena for 3 days, then return to Florence before going North and south (relatively)?

We haven't reached retirement yet (You're lucky Larry42!) , but are just as interested in delving deeper into each city.

This trip is a second attempt at visiting Italy - our first was cancelled due to COVID, so the enthusiasm for Italy here has us very excited.

We're so appreciative for all the advice - this is a wonderful community. Thank you, Thank you.

You mentioned possibly splitting your time in Rome; there are a couple of reasons that might be a good idea. For one thing, there might be a restaurant or gelato stand that you really liked, and so you could return to it when you go back to Rome. Another advantage is that when you return to Rome the city won't feel quite so foreign and mysterious; you'll feel a little bit more comfortable since you had already been there before. Personally I like going back to a place, the familiarity is nice.

Re Siena: there's an underground parking lot in front of the train station that's quite handy for getting in and out of town while remaining well clear of the ZTL's. Cost was 2 Euros per day when we last visited and we never had any issues finding a spot during a 5 night stay.
We made it a point to enjoy the town in the morning and later in the afternoon in order to avoid the midday tourist rush, spending the days meandering around the Tuscan countryside which frankly was our favorite part of the trip.
Do take care not to get cross-threaded with the very strict Italian drink driving laws.

Given your travel dates, second the idea of splitting Rome time. I have driven in Italy and, if you wish, renting a car to travel in Umbria or Tuscany is advantageous as well as relatively easy. Robert is correct about the garage at Siena Station. Other parking lots are expensive. Do remember to check out at the indoor kiosk, not at the exit gate. (There is a free parking lot at the Orvieto train station as well). In Rome, visit the Pantheon and then go to nearby Gelateria della Palma (19 via della Maddelena) for 150 flavors of gelato.

Fantastic! Thank you all for the great advice and feedback. We think we'll modify our itinerary to something like this:

Aug 24-27: Rome (Pantheon, Coliseum, learn the neighborhoods via a walking tour: Travestere, Jewish Ghetto, Appia Antica).
Aug 27-30: Siena - we'll stay in town and hire a driver for the wedding events. We'll have the full day to explore the town on August 29th.
Aug 30- Sept 5: Florence (Uffizi, Galleria, Duomo, etc. with day trip to Pisa)
Sept 5 - 11: Venice
Sept 11 - 14: Rome (The Vatican, Tivoli gardens?, Villa Borghese, open to other recommendations as well!)
Depart on the 14th

Please let us know if there are some particular gems we should take advantage of now that we're staying in each city for a longer period of time.

I would take one night from Florence and give it to Rome at end. You will coming from Venice so your first day is mostly gone.
That gives Florence 5 nights and Rome 3 and 4 nights

Consider doing a food tour during your first stay in Rome
Tons of fun and since you will return to Rome you can return to any place you especially liked on the tour

EatingEurope.com

Assisi is a lovely town, I would give it 2 nights
You could fit it between Venice and Rome
Train would be a change in Florence

I will comment that when I was using a Garmin for navigation (today, I would use Waze), it was impossible to get the Garmin to give me a route to the "other side" of Siena (for example, to a large parking lot) that did not use the fewest possible miles, and thus go directly through a vast amount of ... ZTL! I tried this again and again from various locations.

I'm only using this newsboard as a citation, but it APPEARS that, NO, there is no navigation tool, or even an online set of maps, to de-mystify where the ZTLs are. And I'm going to contradict the people who say, "The signs are easy to see." That's not true when you are driving safely, looking at cross traffic, all regulatory signs, and pedestrians. I'm not even charging that the ZTL signs are designed to be inconspicuous, which I am inclined to believe.

I'm not opposed to ZTLs, I'm just answering your question.

Thank you, all! Between the ZTLs, the encouragement to enjoy the Tuscan wines, and confirmation that there are transport alternatives, we are definitely going to forego driving.

Again, truly appreciate all the wonderful advice.

Best,
Abbiocco