Hi.
We will be in Tuscany mid May with a car. We will be staying in Castello di Casole. So far I made this itinerary... Anything I am missing or need to remove. The # of days are firm.
Day 1 (1/2 day)
Contrade walk
Medici Fortress

Day 2
Piazza del Campo
Torre del Mangia
Duomo
Santa Maria della Scala
Piccolomini

Day 3
San Quirico d’Orcia
Pienza
Montepulciano
Bagno Vignoni

Overall you've packed too much "check off been there seen that". What experiences do you actually want to have?

There is a lot of overlap between day and day 2. I would not rate the fortezza as a top destination. It's a good landmark for the bus depot, and the location of the Wed market, but other than a quick walkby not worth a detour IMO.

Day 3. I recommend you put those destinations into google maps. It'll be 3-4 hrs of sitting in a car, and that's not counting time to find parking, etc. Sounds like a horrible day to me.

Based on the hotel you've chosen I recommend you redirecdt your plans to sights that are much closer, eg visit San Gimi on day 3, and forget that long trek halfway across Tuscany.

There is a lot to see in Siena itself without day trips in a short stay. Here is my itinerary from quite a few years ago now…



Also, I stumbled across this but in St. Francis Church is the Miracle of the Eucharist. https://www.206tours.com/cms/shrine-...na-pilgrimage/

If I might make a suggestion: Rather than posting a million different daily itineraries (aargh!), think through your priorities. Plan your days -- each of them! -- to make sure you see the things that are YOUR highest priorities -- as in the one or two things you most want to see / experience. Consult maps and timetables to think how you might incorporate lower priorities into your day if time permits.

Think about when you will want to take breaks. And what you want those breaks to be. (Lunch? Wine? Coffee and a snack? etc.)

NONE of us can tell you how to maximize your time. We don't know how long it will take you to walk through a plaza -- will you proceed apace or will you stop to take a photo of each corner and to sip a glass of wine and people-watch? Will you explore each and every corner of the places you enter or just march through? If you find a view you want to photograph, will you snap and leave or wait the 15 minutes or so it might take to get that view without others in your image?

IME, Fodorites can be extremely helpful if asked meaningful questions. I'm not sure that asking them to look at day-by-day wish lists will prove productive. In contrast, questions with a bit of context can be useful. For example, I asked, on one of your MANY other threads, why you chose the places you listed. If you responded, I didn't see the answer. Maybe others see it differently, but really, I don't think I can help with endless threads, each just listing some (not all!) potential sights in any particular place with no explanation of why them, why not others, why this order, etc.

Good luck with your planning!

I understand what you are saying about threads. Before I posted new ones I asked whether I should or shall I post all the rest of my itinerary in the same. I was told to put it into a new one - so I did.

problem is that we like everything in a vacation, food, culture, walks, scenery, history, etc. so it’s difficult to say what’s most important for us. One think I can say, we like a good mixture of stuff. I would not spend a full day on the beach or a full day in a museum.

I also don’t run around like crazy checking off boxes. We like a descent pace with lunch, dinner just walking around, enjoying the moment. If we
dont Get to something on my list - no prob for me. I do like to make sure that we do cover the things that should not be missed. I look at them online, with images - but it’s hard to tell whether I want to see it or not compared to other things. Makes sense?

IMO, you would do far better -- FAR better -- with a decent guidebook. The Michelin Green is excellent. The Rough Guide is superb. You can consult various options at your local library. A good guidebook covers all your options, with descriptions that will allow YOU to decide what is a priority. Again -- NONE of us can tell you what will satisfy your particular interests.

P.S. Starting a new thread was a good idea when you asked, because the TITLE of your thread drives responses. Starting a new thread for each and every day or two of your trip is not such a great idea. JMO.

Get the Rough Guide
Map it out
Too much, day 3 with even a snack for lunch is not possible

If you're staying at the Belmond, it's fabulous and would be hard to leave for daily excursions. But it's not in the right location for what you want to see/do in 2.5 days. The drive to Siena and parking will take 40-45 minutes, and Siena is perhaps not the small Tuscan town you imagine. It's a fairly good-sized city with lots of traffic circulating outside the ZTL.

Rather than the Val d'Orcia on Day 3, I'd stay in the Val d'Elsa area, see San Gimignano, Volterra. Or drive into Chianti to Castellina, Radda, Panzano. Either would be half the time in the car as driving to/through the Val d'Orcia and provide a much more relaxed pace.

You're itinerary looks like visiting stall places rather then visitng some historical landmarks.

Actually this looks really good. My main focus of that day would be on the wineries (both from the esthetic and quality point of view). How do you compare Chianti wineries vs Montepulciano. I mean from the landscape, the way the winery looks, etc.

This route - also takes about 3 hours from and back to the hotel.
Val d'Elsa
Castellina
Panzano
Castello di Volpaia
Radda
Castello di Brolio

6 destinations, 3hrs total drive time. Gives you enough time in the parking lot of each winery to jump out of the car, take a few pictures, throw back a splash of wine, run around the car a few times and be off.

You couldn't pay me to have a day like that. But of that floats your boat then go for it.

Well, this sounds a lot like the pace you imagine for your time at Lake Como.... I just don't travel like this, and the route I suggested upthread would be all I'd want to attempt in a day. I live in California, so the winery stops aren't my priority while in Italy. But if you want to visit a particular winery or two, you need to find out if a reservation is required. Not all wineries accept "walk ins."

Do you mean Chianti, the town or the Chianti 5 regions?

Montepulciano is very pretty and pretty steep.

I have few wineries on the list. Will definitely make reservations and will not visit all. I will pick probably 2 and thats it. I was just wondering what direction, Chianti area or Montepulciano area. I heard Montepulciano is nicer / more dramatic.

What's "nicer"... an apple or an orange?

if you're still considering the Val d'Orcia, you need to be (more) realistic about the time needed to get there, time needed to park and walk in/out of the historical centers. Driving speeds between rhe smaller towns are low. A winery stop is not just a stop, it's a visit and can take a lot more time than I think you're allowing.

I am leaning more towards the Val d'Orcia... What wineries in that area will have the most dramatic / scenic effect? I would go to 2.

Are your decisions based on pretty wineries, the quality of their product or specific varietals? Do you want to visit a winery where you could also have lunch? Do you still hope/plan to visit any towns the same day? If so, which ones? Because you'll already be driving about 4 hours* to/from the Val d'Orcia, you need to develop a logical route not necessarily based solely on specific wineries or towns.

* Based on driving mostly secondary roads, not main roads, and not counting stops/detours for anything interesting along the way. Such as the beautiful Abbazia (abbey) di Monte Oliveto Maggiore.

Important: If you want to taste several wines (and not spit), you'd be better off hiring a driver for the day. Drunk driving is taken very seriously in Italy. Lower blood alcohol limit (0.5%), and higher/stricter penalties.

I am OK with a glass or 2. Thank you.
My current list for that day is the following
Castello di Casole -> San Quirico d’Orcia -> Pienza -> Palazzo Massaini -> Bagno Vignoni (If I have time) and back to Castello di Casole

"I am OK with a glass or 2. Thank you."

Both in Italy and France you get traffic cops pulling over everyone leaving a town and testing everyone
being "ok" isn't the point

You might also like the Monastery of Mount of Olives to the east of Buonconvento
Bagno Vignoni I would probably miss but then again I would miss Pienza though I know many Americans like it.

OK Great. Also, is it worth going to the Montepulciano city itself - or just the wineries?