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Tuscan road trip for 3 days itinerary help- late Oct 2018

Los Angeles, CA
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8 posts
54 reviews
Tuscan road trip for 3 days itinerary help- late Oct 2018

A variation of this question has been asked many times, and I have read many of them. But would like some advice nonetheless please. We have 3 days with a car to drive around Tuscany, Oct 26-28.

Picking up a car at Florence airport early in the morning, about 8:30 am.

Driving straight to our hotel at San Gimigano, so we don't have our luggage sitting in our boot. Drop off luggage, get back on road.

I heard the SR222 is one of the most beautiful roads in Chianti, so thought we'd drive up it a ways, maybe hit up Castellina in Chiant, Panzano and/or Greve (assuming this is too many towns, which one should I cut out?)

Second day, spend morning in San Gim, drive to Siena spend the day in Siena. Drive back to San Gim and spend 2nd night in our hotel.

Get up early, drive to hotel in Montepulciano, drop off bags, go to see Peinza, San Querico d'Orcia and/or Montalcino (once again, assuming this is too much for one day, which one should I cut out?)

Overnight in Montepulciano, have to drop off car in Orvieto by noon at train station, want to spend a few hours in Orvieto and then take the train to Rome.

Thinking I might only get to see one town in the Val d'Orcia if I want to spend any time in Montepulciano as well, so any suggestions on a reasonable itinerary would be helpful as well.

Thanks!

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9 replies to this topic
Montepulciano, Italy
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for Tuscany
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1. Re: Tuscan road trip for 3 days itinerary help- late Oct 2018

At first glance I think this works fine but let's take a closer look.

Day 1. By the time you've checked in at San Gim it should be late morning so still a good part of the day left to you. Definitely head over to Castellina (40 mins) but then go on to Panzano via Radda. Late October the days will be shortening and if you hit iffy weather it could be gloomy by mid-afternoon so personally I would wait and see what the day is like before committing to anything further. However, up to Greve on to Montefioralle over to Sambuca and then back to Poggibonsi / San Gim would only add another 40 mins or so. Distances are short and all the towns mentioned can be explored in 30 mins to an hour.

Day 2. If it were me I would head to Siena first to spend as much of the day as possible before returning to San Gim. Even in October you'll still find tour buses in the town until around 4.30 / 5, especially on a weekend.

Day 3. (BTW, I love it when people volunteer to have an early start!) This should work too, note it's around 90 mins drive and do take the beautiful route to Montepulciano via Taverne d'Arbia (outside Siena), Asciano, etc going across le Crete for the sensational views making the journey there a big part of the pleasure. Even with the inevitable stops for photos, if you really have left early enough you should be in Montepul by 10.30. Head over to Pienza (15 mins drive) to explore the tiny village, then on to either San Quirico or Bagno Vignoni for lunch. Up to Montalcino in the afternoon (do visit the fortress) and then back. Its a long day, sure, as you will have had the early start and fairly long drive first thing, but all the rest is very manageable.

Day 4 works well too. All-in-all a nice few days, busy certainly with a fair amount of driving but not overly so. Fingers crossed the weather is on your side but it can be very unpredictable around then. Enjoy!

Wantagh, New York
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104 reviews
2. Re: Tuscan road trip for 3 days itinerary help- late Oct 2018

Will the towns of Montalcino, Montepulciano and San Quirico be closed up around siesta time.. is one town better to plan on for the afternoon that is more active...wine shops open and any sights??? Want to hit all 3 in a day but don't know which one I should plan on for after lunch or for lunch and afternoon...Thanks!

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for Florence
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3. Re: Tuscan road trip for 3 days itinerary help- late Oct 2018

12soup-er

The small towns I know in Italy tend to respect siesta time. Plan on taking a leisurely lunch and getting to know the restaurant/cafe/whatever pretty well before much of anything begins to stir around 4:00 -- or plan on walking around a town that's largely deserted -- except for other unfortunate tourists like you.

We recently found ourselves in the fascinating village of Scarperia -- arriving just as everything, public and private, including, to our intense dismay, the superb Palazzo dei Vicari, was closing for lunch and siesta. We were delighted to find one cafe open, had a terrific lunch, and then explored the totally closed-up town (looking in the window of one knife shop after another) until the palazzo and everything else started opening up again.

Larger and more touristy towns tend to be less totally shut down than smaller, less touristy ones, but I remember Montalcino being pretty inhospitable to us one hot afternoon. The only place we found to spend the mid-afternoon hours in the shade was the Medici castle at the very top of town, which was then an enoteca.

I do think your phrase "Want to hit all 3 in a day" is most unfortunate. If it were me, I would think in terms of "enjoy" rather than "hit". And if I found myself in any one of those three towns -- or any other place -- and found it fascinating -- as I happen to find Montepulciano -- then I would be strongly inclined to abandon any rigid schedule and spend as much time in Montepulciano as possible.

Wantagh, New York
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2,359 posts
104 reviews
4. Re: Tuscan road trip for 3 days itinerary help- late Oct 2018

We don't have a rigid schedule but with limited days and knowing those 3 towns are fairly close together, I just want to try to maximize our time and if one town will be more "awake" than the others, we would plan accordingly..... thank you!!

Montepulciano, Italy
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5. Re: Tuscan road trip for 3 days itinerary help- late Oct 2018

It's actually very difficult to explain just how different these towns are in late October to how they are today. I had a conversation only last week with some British visitors who assumed what they were experiencing was typical of year round when it most certainly isn't. Our season in the southern Tuscan hill towns is relatively short - besides Easter and a few spring public holidays, it's mid-May to early October - so you make a good point about what's open and what isn't. Definitely not San Quirico during the afternoon where some of the tourist focussed stores will have closed for the entire winter by the middle of October if not before. It's a town that is "on the up" but not that up just yet. Montepulciano - larger - is possibly better but, even so, this is a fairly quiet time so again the mid-afternoon pausa will have to be respected. Montalcino is possibly your best bet but I would only expect the wine stores to be open between 13.00 - 16.30, all other shops having closed. Please don't be put off for it is a far, far nicer time to visit than right now, just plan carefully, as you appear to be doing.

Los Angeles, CA
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8 posts
54 reviews
6. Re: Tuscan road trip for 3 days itinerary help- late Oct 2018

Someone hijacked my question, but that's ok, the more info I can get from the lovely people at TA, the better!

Thanks lastraniera, this advice is very helpful, and I will definitely make a note of your suggestions! I do realize it's an iffy time to go, weather wise, but as Venerosi pointed out, better then than now, when it's overstuffed with tourists and super hot as well! Fingers crossed the weather is kind to us!

I'm not so bothered about the tourist shops being closed up, as I don't do much souvenir hunting anyway. If I find something locally crafted I may buy that, but as another post pointed out, those sorts of things are pretty rare to find nowadays (I saw it most in Japan, where the artisan spirit is very much alive and well). I'm mostly in it for the drive around the countryside and walking the cute towns.

Will have to keep the siesta in mind, however, to plan around lunch, as it would suck to be really hungry yet no restaurants will be open for hours.

Birmingham, UK
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486 posts
139 reviews
7. Re: Tuscan road trip for 3 days itinerary help- late Oct 2018

If you are staying in San Gimignano spend time there early and late in the day when it will be quieter.

Siena deserves as much time as possible, certainly a complete whole day.

Late October is a good time to go although the days will be shorter.

Montepulciano, Italy
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for Tuscany
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9,150 posts
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8. Re: Tuscan road trip for 3 days itinerary help- late Oct 2018

Sorry you felt hijacked, Tracy, but don't worry, we're still here to help. Re your comment, "it would suck to be really hungry yet no restaurants will be open for hours" that is almost impossible to happen nowadays even in low season and somewhere small for there are so many open-all-day bars and cafes serving food from just a quick panini to a plate of pasta. However, if you want a proper two or three course lunch in a formal restaurant, best to find somewhere before 1 / 1.30.

Los Angeles, CA
Level Contributor
8 posts
54 reviews
9. Re: Tuscan road trip for 3 days itinerary help- late Oct 2018

Oh no worries, I was just joking about the being hijacked thing! The info I got from people was great for me, and 12soup-er as well I'm sure.

Good to know about the lunch thing. Will plan accordingly.

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