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Tuscany itinerary on october through november 1st weekend in Italy

ghiggifg

New Member
Hello! I 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.
 
One advantage of the countryside, is it doesn't need lots of people, and indeed it might be a positive to enjoy quietly.

Coming at it from the reverse direction, have a look at events that are happening, so if you want to feel part of a vibrant / live feeling, an event or festival can be very enjoyable indeed... and for many there will be a high proportion of locals / Italians vs. international tourists.

Our experience of the weather at that time of the year has often been favourable, often comfortably warm, but never hot, with the odd day / part day impacted by rain, but with a little flexibility to re-jig an itinerary, never enough to get in the way. However if you're forced to nail the days in by virtue of changing base every day or two, then that removes flexibility. The answer for me (but may not suit you), is to settle on a single Tuscan base and then have 4-5 day trip 'options' available. Let the weather report when there guide you to the option best suited to that day, be it a day trip into Florence or Siena or Lucca, or a chilled drive through the countryside.
 
Coming at it from the reverse direction, have a look at events that are happening, so if you want to feel part of a vibrant / live feeling, an event or festival can be very enjoyable indeed.
If you want to something "vibrant and alive", the Lucca Comics and Games Festival should be happening around that time. It is like nothing else you will experience - fantasy costumes and displays juxtaposed against the backdrop of a renaissance town. Lucca becomes quite crowded - but very alive.

Adding a few pictures so you get the idea:
 

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One advantage of the countryside, is it doesn't need lots of people, and indeed it might be a positive to enjoy quietly.

Coming at it from the reverse direction, have a look at events that are happening, so if you want to feel part of a vibrant / live feeling, an event or festival can be very enjoyable indeed... and for many there will be a high proportion of locals / Italians vs. international tourists.

Our experience of the weather at that time of the year has often been favourable, often comfortably warm, but never hot, with the odd day / part day impacted by rain, but with a little flexibility to re-jig an itinerary, never enough to get in the way. However if you're forced to nail the days in by virtue of changing base every day or two, then that removes flexibility. The answer for me (but may not suit you), is to settle on a single Tuscan base and then have 4-5 day trip 'options' available. Let the weather report when there guide you to the option best suited to that day, be it a day trip into Florence or Siena or Lucca, or a chilled drive through the countryside.

Yeah, I'm thinking about going there on the more vibrant / live days, that's why I'm not liking the idea of the november 4th (monday) in San Giminiano and Monterrigioni, maybe pulling the whole coutryside one or a few days earlier.

My base for the coutryside would be just Siena, also having in mind a little flexibility.

Also, thinking about skipping the Dolomites in this trip (no withou sheding a tear hahah), to return another time of the year in a drier season with more time to spare in the region. This would give me 3 more days to be in other locations and could help with the itinerary's flexibility.


Festival should be happening around that time. It is like nothing else you will experience - fantasy costumes a

Surely going to look more into it. Thanks!
 
Also, thinking about skipping the Dolomites in this trip (no withou sheding a tear hahah), to return another time of the year in a drier season with more time to spare in the region. This would give me 3 more days to be in other locations and could help with the itinerary's flexibility.

I'd very much echo your thoughts. We've very much enjoyed time in the Dolomites, but on a hectic romp around Italy, it doesn't fit so well.

FWIW what worked for us on another holiday was Bologna / Verona / Lago Molveno (and then followed by a Lago Molveno / Trento / Bologna follow-up). The logistics of each of these was very manageable with fast 'freccia' train service and Bologna a very convenient entry or departure airport. There's also a coach service from Trento to Molveno, but on the first trip we drove from late into the Verona leg. As for time of year, we've been in May and early October, and both are somewhat quiet around Molveno, being outside the summer and winter peak seasons. Good for accommodation, but ski lifts not running as frequently, and restaurants have more nights off. Still recommended though - I think it's a great time of year for the weather.

Indeed I reckon Bologna might be best saved for a trip that does it justice. It's something of a food lover's haven, and as such I'd recommend getting an apartment if you take joy in grazing specialist food shops / markets. It's also got a vibrant student scene, plus it's a proper city, not beholden to tourists, so it wears them well. A taster day can be good, but we did that with Bologna on two occasions and it fell a little flat, partly as by the time we'd got to the train station, caught the train, then got from train station to the city itself, energy levels had dropped a bit... and for me it's a city that rewards exploring on foot. Luckily we gave it another go, staying a bus ride away in Rastignano, and being able to bus directly into the heart of the city transformed the experience for us. We've since returned a few times.

Glad there's just that single base for tuscan countryside (Siena). I'll also throw in an option of Colle (di) val d'Elsa (oddly nicknamed Colle by the locals, as if it's the only 'hill' around!). Pleasingly under-touristed, yet still attractive, and with an interesting local industry (glass making). If Siena still has the Friday morning farmers' market (in the old marketplace just off the campo), then that's a firm recommendation. In a city where the food disappointed us (restaurants and specialist shops), that market conversely is right up there for quality of produce. Not many stalls, but each one very good indeed.
 
You'll be there for chestnut festivals and olive harvest (if they have one -- 2023 was a disaster for our part of Tuscany). Will give a huge vote for the Lucca Comics Festival. It is crowded and hectic, but also a visual delight. Taking a train into the city from an outlying station solves the problem of finding (non-existent) parking.

We've found that the weather takes a real turn towards cold around the middle of October, so think about what you're packing.
 
Your itinerary seems very ambitious. I agree with your thoughts to skip the Dolomites.

As to the weather, who knows. The norm could be for warm and dry and it turns out wet and cold, or vice versa. The best you can do is look at the long range forecast before you leave and plan your clothes accordingly.

Either way, whatever the weather, I've never let it spoil a vacation. Just roll with the wave! :)
 
Yes, I would also skip the Dolomites at that time of year unless you want a quick trip up to Bolzano to take a sample peek. The local buses go into the mountain villages regularly from the railway station there - you could just stay on, sample the amazing views, and head back to Bolzano for the night. You could probably do the same from Trento. One gem we found near Bologna was Brishigella. It's foody heaven and a stunning little place. It's on the route of "Dante's Train" which takes you from Faenza (a short train hop from Bologna), past some beautiful villages to Florence. This is a normal commuter train but is a lovely way to get from Florence to Bologna or reverse. Last trip we stayed at Brishigella and caught the little train to Florence, then connected to the EC to Bolzano.
 

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