Tuscany itinerary on october through november 1st weekend in

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1. Posted by ghiggifg (Budding Member 3 posts) 7w Star this if you like it!

Hello! have purchased plane tickets and putting together an itinerary to go to Italy between October 19th and November 9th, 2024, arriving in Milan, Verona, a quick two-day trip through the Dolomites just to get an overview, Venice, a day tour in Bologna on the way to Florence , a few days in the Tuscany region, and finally Rome.

In the current itinerary, Florence and the Tuscan countryside (Siena, Val D'Orcia, Pienza, Montepulciano, Moterrigioni and San Giminiano) are after Bologna (28th), between October 29th and November 4th.

I know there is the November 1st public holiday, which will be on a Friday, causing an influx of locals on vacation. I've read that after the holidays, the Tuscan countryside becomes more “dead” with closed shops, almost no people, etc.

On the other hand, I'm afraid that during the holidays and weekends the city of Florence or Pisa will have compromised tours or that I won't have contact with the “live” city.I didn’t want my stay in Florence to feel like a place “blacked out” by the holiday, nor for the Tuscan countryside to have closed or “ghost” towns after the holiday or on the weekend from November 1st onwards.

Also, I feel like the earlier I go to the coutryside, the better chances I have to get good climate and some sunny/dry days.Anyway, my question is which of the alternatives below would be “better”:

(1) Florence/Pisa first, from 10/29 to 10/31. On November 1st (Friday, public holiday), take the Via Chiantigiana to Siena. On 02/11 and 03/11 (Saturday and Sunday after holiday), tour in Siena and Val D'Ocia. On Monday, November 4th, post-holiday, pass through Monterrigioni and San Giminiano and return to Florence, just to stay overnight and then go to Rome by train.

(2) Siena/Coutryside first, leaving on 10/29 via Via Chiantigiana, 10/30 and 10/31 visiting Siena and Val D'Orcia going to Montepulciano; the other day, the trip to Monterrigioni and San Giminiano on November 1st (Friday holiday), returning to Florence to stay in the city and get to know Pisa, from Saturday until November 4th.

(3) small change, also doing Siena/Countryside first, but leaving on 10/29 via Via Chantigiana and going that same day to Monterrigioni and San Giminiano, staying overnight in Siena. Then Siena city tour at 10/30. On 10/31, visit Val D’Orcia and go to Motepulciano. Return to Florence on November 1st (holiday) morning, and do Florence and Pisa between November 1st and November 4th, to go to Rome on November 5th. In this case, I get a day in Florence or Rome, or I can add another part of the Tuscan countryside, since I unite San Giminiano and Monterrigioni on the first day.

(4) change the travel itinerary so that the Tuscan countryside is not on November 1st.

Thanks, and sorry for the long message.

2. Posted by BeateR (Full Member 266 posts) 7w Star this if you like it!

I cannot answer your questions about the cities, because we don't like cities. But yes, Tuscan countryside will be very quiet end of October and November.
But I have some questions to your first days: you wrote, you'll have 2 days for the Dolomities. Do you mean 2 nights in the mountains, or are the 2 days ment from Milan, so only 1 night in the mountains? And where to the Dolomites are you thinking to go, Dolomities is a very large area. For example to St. Ulrich it is a 4 hours drive, only if there is not the usual traffic jam. So you'd have very less time for an overview.
And Oct/Nov. could be very bad weather in the mountains, with rain, fog, so not the best time for a road trip.
Did you notice, that on your way to the Dolomites you come around Lake Garda. You could drive the eastern side of the lake, it is a wonderful and scenic drive. And stay one night in one of the towns on the lake, Bardolino, Garda Town, Malcesine or maybe Torbole.

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4. Posted by ghiggifg (Budding Member 3 posts) 7w Star this if you like it!

Quoting BeateR

I cannot answer your questions about the cities, because we don't like cities. But yes, Tuscan countryside will be very quiet end of October and November.
But I have some questions to your first days: you wrote, you'll have 2 days for the Dolomities. Do you mean 2 nights in the mountains, or are the 2 days ment from Milan, so only 1 night in the mountains? And where to the Dolomites are you thinking to go, Dolomities is a very large area. For example to St. Ulrich it is a 4 hours drive, only if there is not the usual traffic jam. So you'd have very less time for an overview.
And Oct/Nov. could be very bad weather in the mountains, with rain, fog, so not the best time for a road trip.
Did you notice, that on your way to the Dolomites you come around Lake Garda. You could drive the eastern side of the lake, it is a wonderful and scenic drive. And stay one night in one of the towns on the lake, Bardolino, Garda Town, Malcesine or maybe Torbole.

Thank you for the reply and the tips!

(1) About the Tuscan coutryside, what I would like to understand is, in theory, would I make the most of the trip at the region by visiting the countryside of Tuscany or Florence: (a) before the holiday/weekend; (b) during it; and (c) from november 2nd onwards?

(2) About Dolomites, I meant 2 full days. The idea is to get a glimpse of the region, as I do want to return on a future trip with more time. It would be 1st day (10/22) leaving from Verona by car early in the morning and stopping at a couple of vista points. Then, 2 full days to explore a couple of points of interest and maybe a hike (Lake Federa, Giau Pass, something around Stella Pass, Lake Braies). Finally, the last day (10/25) driving by the morning to Venice, or back to Verona (but I believe the train ticket would cover the price of the surcharge). About where were I planning to stay on overnights, in this order of preference: 1) Cortina D'Ampezzo; 2) Ortisei; 3) Bolzano.

I could make this part adjustable to skip the Dolomites depending on the weather to do someting else by northern Italy on these days (like around Lake Garda, an extra day in Venice, maybe a day in Padua or Trieste).

Alternatively, just ignore it beforehand on this trip, leaving it for the future, and add more days on other places (Rome/Florence or even choose to explore more the coutryside of Tuscany rather than going to the Dolomites, or adding some backup days in case the weather doesn't help here or there).

(3) I did notice Lake Garda, and thought as a second option if the weather was bad. Surely going to look more into it.

Thanks again for the reply!

5. Posted by ghiggifg (Budding Member 3 posts) 7w Star this if you like it!

Oh, and I think it's worth to mention. Even though I say I plan to come back to Italy, It's not that easy, as I live in the coutryside on the southern most state of Brazil, tickets are expensive nowdays and takes a good amount of time and good planning to cross the ocean on vacation. That's why sometimes it feels like leaving something aside or one less/extra day somewhere is a very hard decision.

6. Posted by BeateR (Full Member 266 posts) 7w Star this if you like it!

ghiggifg, I totally can understand you. Yes, travelling is getting more and more expensive, also for us.
As you have 2 full days for the Dolomites I would try to go there. You always can cancel it if the weather is too bad. Bolzano may be the easiest for finding a hotel for overnight, but it is a big city and not in the mountains. So better go to any other town or village. Cortina or Ortisei sound good.
Whatever you decide, you cannot go wrong. Italy is such a beautiful country.