Itinerary Review for Trip to Italy, can add 1 day but where

Day 5 (wed)
Check out of CT town hotel. Need to make our way to rental car place. Likely either La Spieza train station or Pisa airport?
Rent car and drive south. Hope to have time to stop and see town of San Gimignano on way before reaching destination of Montalcino. Stay in hotel inside walls of Montalcino for 2 nights. Appears a few actually do have parking. Ok dropping San Gimignano if we are running late.

Day 6 (thur)
Explore Tuscan countryside for much of the day taking scenic drives and not being rushed and any firm plans other than for myself to be out for a sunrise shoot.

Day 7 (fri)
Check out of hotel. Drive to Ortesi which will be a long ride (5 1/2 hours I believe) where we would check into a hotel for either 2 or 3 nights. Hotel Scherlin in Ortesi has a pool and also playground and other related stuff for my daughter.

Day 8 (sat)
Explore Ortesi and take lift up to Seceda. if time see by car nearby mountain towns like Santa Magdelena, Val Gardena mainly looking for little churches surrounded by large mountains.

Day 9 (sun)
Sunrise photo in Villnoss, one of those said little churches this being a solo effort in the early AM.
Check out, drive through and visit town of Cortina before parking and taking lift up to Rifugio Lagazuoi where we would hopefully have late lunch. Drive to Tre Cime area and have 1 hour walk to Rifugio Lavaredo where we would stay 2 nights

Day 10 (mon)
Location wise it is important for me to be here though to at least try and get sunrise and sunset photos of the tre cime. There is an even better location (Rifugio Locatelli) where accommodations and food are a little better but is too far a hike for them with bags to make it work. I hope we can have lunch there this day.

Day 12 (tue)
After sunrise photos by myself higher up the trail.
Checkout and drive to Venice where have to return the car at the airport most likely.
Take public transit into city and check into hotel for 2 nights.

Day 13 (wed)
Explore Venice by foot both day and night. Sunrise is a must this day and tomorrow.

Day 14 (thur)
Have to get from Venice to Milan Airport for 4 PM flight back to NYC so we would need to be up and out early! And from there short flight that night back home to Bos around midnight.
Hoping this won't be too draining a day but sounds tiring and in a perfect world we would have enough time to briefly at least see from the outside the Duomo in Milan on our way before heading to the airport.
Arrive back home exhausted but have Fri, Sat and Sun to rest before life starts back on Monday

Options adding a day which also means getting back late Friday instead.
Add a day in Montalcino ; if doing so we could likely take the day and see Siena or possibly even Florence as a day trip which I think we could do on public transit and give driving a rest. Or Orvieto which I think I would need to drive to but looks great for a day trip?

Add a day between ride from Montalcino to Ortesi ; a 5 1/2 hour drive is a long one, but I am not sure there is a desirable stop along the way that helps the journey if spread over 2 days. Verona would be one option that would be desirable but with the added time to get into and out of the city, it really does not save that much time and still a long drive from Montalcino to Verona so ideally would be somewhere more in the middle.

Add a day before flying out of Milan in Milan to allow us to see the Duomo and some shopping downtown Milan. Makes the last day easier but not sure the lost day was a real burden.

No real desire to add a night to Venice and hotel cost likely high.

Just thought I would add in case anyone can still read this much:
As far as photography ; goal is to come home with 6 or so amazing images not 1000's of good images so other than dedicated shoots which will be either at sunrise or sunset and some night time I will be just taking snapshots like any other tourist would and photography during the normal day areas is not a priority.

If weather is really unexpectedly bad which can happen in the mountains I will just book 2 nights last minute in Ortesi or elsewhere and forego the Rifugio stay portion and those photo ops. Would be unfortunate and costly to do so but not worth the risk of not having a plan b.

Leaning on booking a 3rd night at hotel in Montalcino and using that day for visiting another town that day: preference for perfect 1 day option out of: Siena, Orvieto, Florence ; no interest in art inside museums just beautiful places and scenery. Love walking through historic areas that have history, love the Duomos, old cobblestone streets, car free areas, etc... if the place is worth going, crowds don't bother us.
Revised plan would be 3 nights CT town, 3 nights Montalcino, 2 nights Orvieto, 2 nights Rifugio in Tre Cime, 2 nights Venice

I did state but obviously with some much written it is easy to be lost among my babble.
Time frame is either last week of August and First week of Sept or First 2 weeks of Sept.

I know I am early, main reason to figure out the schedule crazy earlier is any private rooms at the Rifugio's mentioned fill up so I kind of have to figure out which nights I would need at that location(s).
If the private rooms book, a shared bulk style dorm with others is not going to be an option given we have our toddler daughter.

Orvieto would certainly give you spectacular views, Cortona too if you can fit it in.

Thanks Jim.
I edited my posts above to make it more on point of my current plan.

Would you vote as a daytrip Orvieto over Siena or Florence (having never been to any of the 3)?
Florence I envision 1 day may be rushed and Siena may lack enough to do compared to Orvieto.

Have Rick Steves' hilltown show on my DVR at home and will be watching tonight as I know he loves Orvieto.

if you want panorama photos of the countryside it is Orvieto. Aside, my stay in the Chianti region of Tuscano included Panzano.. If you want to capture in a photo what Tuscany looks like ... you take it from there.

Keep in mind my photography will be planned shoots at certain times only from specific locations.
Tuscany countryside shots are planned for Sunrise already so the extra day does not need to include those..
Otherwise consider me a tourist with a camera like everyone else so more interested in visiting than photography during normal daylight hours.
Extra day I prefer to add place my wife would like rather than for photos

While I am exhausted just reading your itinerary, I understand what you are trying to do. I will offer comment on one area, with which I am VERY familiar.

Day 8 (sat)
Explore Ortesi and take lift up to Seceda. if time see by car nearby mountain towns like Santa Magdelena, Val Gardena mainly looking for little churches surrounded by large mountains.

You will not need to stray from Ortisei to get some great photos. The little church at St.Jakob/San Giacomo offers great views across the valley and of the mountains. It might suit your purposes. Photo here.

Also, the little chapel on the ridge at Rasciesa might suit you and the "hike" is more of a mountain walk, easily done by families, even with strollers. Your daughter will love the funicular that takes you to the ridge.

All-in-all I hope you gert enough time in the Val Gardena/Ortisei. It will be a fun place for the family.

FYI you are not early! August in particular is very busy in the VG so pin down those reservations ASAP!

Thank you Laurel and appreciate you reading the entire plan
Very helpful for Ortesi ; thank you
I would prefer to stay in the immediate area that day since we really only have that 1 full day there
Previously I had 3 nights in this hotel and 1 in the tre cime rifugio but fear of that 1 day weather is not desirable I will be too disappointed so 2 nights increases my odds but will be much less to do there in comparison
Type of photo you posted is exactly what I am hoping we will see that day

Will be early sept at least by the time we are in the dolomites either way but this region is where I do feel the pressure to book very soon
so hard for me to precisely figure out which days we will be there though!
Sounds like you would vote my extra day should be a 3rd night in Ortesi?

I am now thinking instead of orvieto on that extra day as a daytrips to change hotels for 1 night to somewhere just outside Florence
See Florence via public transit that day and then the drive from that area to Ortesi will be at least an hour faster the next day

Great views of Firenze from Piazzale Michelangelo, any time. From the Fortezza, I think you will be restricted to,opening/closing times, but Roberto would know for sure.