Trip is fully booked, thought I would share my plans

If I did change Pienza to 2 nights only. I would move up CT but keep 3 nights there.

Both of these changes may cost money or change of lodging at this point.

I then would move that one day to the Dolomites.
Staying the 3 nights in a row in Ortisei, than the one day at the castle and on the last night instead of returning to Ortesi I would stay somewhere in the Dolomites for 1 night that is closer to Venice (Passo Gaui maybe which was my last planned stop before Venice) and having nothing but driving to Venice planned for that day and drop the car off a early giving us more time both in Venice and in the Dolomites this way.
I think this would be better in some ways but then worry 2 nights for Pienza is rushed especially since day of arrival is still spent mostly in Siena.
Our one full day would be to explore Pienza, driving area around San Quirico and visit Montepulciano, would do without Montalcino in this case.
Also this would be 2-2-3 for the start of the trips lodging rather than 2-3-3 so would start out more rushed feeling.

The whole trip cannot be extended, this is already basically a full 3 weeks which was hard to get off of work and we have never gone for longer than 10 nights anywhere in our lives so this is twice as long as any other vacation.

My wife is hopefully going to amazed at this trip, as Italy is her favorite place on earth and she dreams of going to Paris she might suspect/be hoping for one of these but definitely cannot envision we are going to both.

I'm not sure what you mean by "surprise" trip, as that can mean different things to different people. Obviously you know your wife better than I do, but for me half the fun of a trip is anticipating it. For me the idea of a true surprise trip (as in "Honey, pack your bags. We leave in an hour.") would be horrible. I would also hate to be cut out of the planning. That said, my husband would love to be surprised that way. Different strokes for different folks. I just thought I'd mention it in case you're not sure how your wife might receive this.

Happy travels!

Good point. In this case it would be at least the 3rd "surprise" trip we have been on so I know she actually greatly prefers it this way.
I have always done 95% of the planning and budgeting for our travel so was mostly done by me before, but this just adds the other 5%. She is working as well, so has advance knowledge of our travel days and requested the time off. I have been working on this trip since December.

She just does not and does not want to know our destination. I have to guide her a little as to what to pack of course.
At the airport in Boston she will know we are off to Italy but going to keep Paris a surprise until the day we are on a plane there which is also her b-day.

In our household there has been anticipation for this trip for months now and it is now really starting to build up. I still think she believes we are off to another part of the world she will not enjoy as much and would be lower cost so will be surprised in a good way by the destination(s)

The added elements of the toddler, the car and the amount of time away with so many destinations just made this one much harder to plan than any trip I have in the past especially without her to run ideas off of.

mreynolds, you may have your heart set on San G, but I want to encourage you to think this through... I stayed in San G. for 3 nights several years ago, and found that it has become almost a medieval set piece, flooded with tourists during the day, with the few actual residents in the evening generally closing up shop and going home (tho most seem to now live outside the walls). There seemed to be little actual village or family life left there; I found the town downright gloomy in the evening. On the other hand, I spend 3 nights in Volterra, nearby, last year and loved loved the town. It, too, has much medieval and renaissance architecture and ambience, but is full of active families, schoolchildren, moms and dads pushing strollers along the ancient cobbled streets. There are also significant Etruscan and Roman sites and ruins, wonderful cute cafes and trattorias, and (I experienced) much friendlier people than they were in San G. Take a look at RS Italy book description of Volterra, too. I stayed at La Locanda Hotel, which was quite nice, and, tho hotel is within the medieval walls, was also very close to a public parking lot just outside the walls. Also very friendly craftsmen and women who will explain their art to you as you watch. As you all are shaking off jetlag, what village ambience would most help you feel happily at home in Italy?

jmauldinuu: those first two nights are not set in stone. Reservation is made but could be cancelled.
I did actually go back and forth between San Gim and Volterra , the drive from Pisa airport is similar (Volterra actually a little closer) and the drive to Pienza from either is not bad (San Gim a little closer)

My choice for these first 2 nights was down to these towns or staying in Pisa by the tower.
I had originally planned and booked in Pisa many months ago but changed my mind recently.

I know some of San Gim is not authentic and am ok with that, I really like the totally medieval look it has. I really wanted that look and feel so think I can look past the more plastic nature of the town and locals.
Having never been to either both sounded interesting and both are said to be better in the evening after the tourists leave.
The streets of San Gim look nice to me for strolling around town, less hilly than Volterra.
It is discouraging to hear that the evenings was a time you did not enjoy in San Gim?
I didn't mention in these posts, but I am a photographer that does low light and night photography so dark medieval alleyways and the like that I think San Gim has will offer me some interesting places for me to shoot after dark.

The biggest reason I choose San Gim over Volterra was the hotel. Since I made this booking recently I was not late to find places but late to find a suite or larger than normal room that could accommodate our party of 3. I remember not being fully satisfied with any place I could get in Volterra and then I started looking at San Gim ; found 2 places that looked great, and one that had a suite for reasonable cost (about 155 euro per night) with a balcony and great view, included breakfast for 3, included a parking garage spot just outside the walls, etc... (Hotel Bel Soggiorno)

I probably would have rather have booked a place in Siena but thought the post flight drive would be a little too long combined with likely a more hectic day site seeing there than a smaller town like San Gim or Volterra.
I could look at Volterra again but I think it will again come down to hotel choice not offering as much as what we booked,

Having 3 can at times make you select an area based on lodging options more so than if there were just 2 of us I found.
EDIT:
I did just take a look at Hotel La Locanda and it is available and they do have large room choices also available for similar prices to the place in San G. and similar benefits, if anything larger rooms but none seem to offer a balcony with view which I am thinking was my main motivation when I booked where I did.

I will take a another look at Volterra overall, in general these hill towns do not seem to book as far in advance as other areas we are going to.

So glad to hear that she's on board with the surprise. This is the perfect example of how there's no one-size-fits-all approach to travel. Have a wonderful, wonderful time.

One option for Venice with a 3 year old is the park in the Sant'Elena district. Very popular with the locals, virtually no tourists, lots of things to play on. Here's a peek with Google Maps Streetview: https://goo.gl/maps/G1xPVPZMNE42

Thanks Michael
I have been mapping and noting playgrounds in each area we are staying and had not done so for Venice so this will be useful
Funny how a neighborhood swing or a slide becomes a major attraction

I was in Italy last month and stayed near San Gimignano at a B&B. The drive into town was short and I would highly recommend staying there. We had a 2 nighter booked but reserved an additional night because we loved it so much. From there we drove to Siena and other sites. We are booked there again this time in August. On the other hand traveling with a 3 year old will be challenging. I personally would not do it as I know my 3 year old grandson would not be happy doing this trip lol. I do hope you report back to us how it went. I am happy you are able o surprise your wife. http://www.casolarelibbiano.it/

Have you considered staying in Lucca? You mentioned Pisa, that is why I asked. It is a medieval town, very family-friendy. You can walk the wall with a toddler, and there are playgrounds scattered throughout.

I did look into Lucca
My take only:
Seems like a charming town, love the fact the entire area is car free inside the walls and the thought of renting bikes and biking around he walls sounds like fun to me
That said to my wife that may not sound ideal and I feel like Lucca is too lacking in attractions to visit, I actually do want touristy and tourist things to do and see for the initial first stay
Sounds relaxing but maybe too much so
My impression only is Lucca is the kind of town that lacks that wow but is one that really leaves an impression on you and you want to return, San Gim is kind of the opposite with lots of wow factor but likely a place once you have been you would say been there done that.
Given the choice for 1st destination I would prefer the initial wow factor

I just returned from a 16 day driving trip which included most of the first half of your itinerary. Wanted to share a couple things you might consider. One of the highlights of our trip was the day we visited the abbey near Montelcino (missed the Gregorian chants as the times were confusing...even for our Italian hosts who checked their website), but happened upon a Sunday service with a choir which was magical.

This was also our day for seeing the countryside. En route to one of the best meals of our lives, the nav took us through Monte Amiata which was also one of the most scenic drives of our lives. (We heard many Tuscans don't go here. I can't imagine why!) Highly recommended. Pristine forests, wild flowers, just breathtaking. Ended up in Piancastagnaio at Ristorante Ana, which was amazing. (Get the chestnut-porcini soup!)

We stayed in an agroturissimo near Pienza which was wonderful, but in future, I will likely rent a small apartment to save $ (you can get a week in a castle tower in some of the smaller hill towns for $300 to $500...See the Little Roads of Europe website and also take their restaurant recs!). This would be so convenient with a baby too, although I see you're already doing that in Manarola.

Our strategy for avoiding CT crowds worked really well. Drove to nearby Porto Venere for lunch and a visit to the church there. (Beautiful!) Then parked at the La Spezia train station around 4 pm, headed to CT on nearly empty trains as all the day trippers were leaving. Vernazza was the only town there that still had many tourists. Had another amazing meal at Ristorante da Billy in Manarola. (You REALLY gotta go if you're staying there anyway. Make a reservation as it's packed with locals and also get the seafood antipasto. They brought 12 dishes to our table!) Enjoyed a panoramic sunset view of the Mediterranean. Enjoy!

Thank you ck!
Good to know the abbey outside of Montalcino was such a worthwhile stop!
I had mentioned doing this or Orvieto but really planning Orvieto just going to throw it out to my wife after we are in Pienza.
I think we are better off driving slowly through the areas around Pienza and seeing things planned and unplanned in route one day to Montepulciano and the other to Montalcino.

Our rental apartment in Manarola is actually above restaurant da Billy, I guess a few floors up so will be sure to eat a meal there if we can reserve a table (hopefully not too formal with a 3 year old too formal does not work well)
Will check out Little Roads of Europe's website.

mreynolds, sorry it's taken a couple of days to get back to you with your very thoughtful questions and insights. I did find San G more moodily photogenic. If you have a room with a balcony looking out over the valley, you will likely get some amazing shots. When I answered earlier, I was focused on your having a 3-year-old in tow, and reflecting on which Tuscan hill village might offer your family both the medieval ambience you are seeking, and a fairly family-friendly atmosphere. I did enjoy photographing Volterra, and you will find ancient alleyways there, too. Have you looked at the many photographs that people have posted on the tripadvisor dot com website, for both San G and Volterra? This might give you a better sense of the architecture and light present in both locations. I actually did not find Volterra's hills difficult (except the one route up to the large park at the "top" of town). One note: the old town of Volterra is rather larger than that of San G, so if you are seeking small piazzas, open-air cafes where locals gather, and fun strolling areas in the evenings, Volterra does have more to offer, I believe. Volterra also will have far fewer tourists, both days and evenings, and more residents living their lives. So: this is a win-win choice! Hope you and your family have a wonderful time. Also: If you end up at La Locanda in Volterra, I suggest you inquire if you can have a room on the back courtyard, which has small trees and sitting areas.