Italy Itinerary Help! Dolomites and Florence Aug 11-21

August 15th is the biggest holiday in Italy. This is when Italians take vacations, more than Christmas. So you'll want to make sure things you want to visit will be open (the winery on the 17th, for example). Obviously, you can hike and enjoy nature, but restaurants or even hotels may be closed.

During August Florence is likely to be scorching hot. ( Like a hot & sticky 90 degrees). That—along with you having no desire to see museums—might make it a good call to skip it and move on to the coast.

That makes sense, we are from Southern US so 95 degrees is a normal day for us in the summer. But, we are more interested in the coast, so thanks for that input!

Why Florence twice? (not even sure you need to go once given your stated interests) You can travel from CT to Rome by train and bypass Florence.
I don't understand Aug 17-19--why not just stay in CT?

Yes, Florence is super hot that time of year. So is Bologna. But Bologna has the porticos, so you can be under shade most of the time. Florence does not have the same level of shade.
Driving around the Dolomites is wonderful. Hopefully you can also make time to go up the cable cars/lifts. Being able to enjoy a cool beverage with a view over the mountains is a whole different level of magical.

(The August 15 holiday is no joke. We were in Bologna August 15 a few years back and even the McDonalds was closed. So that's a good day to plan ahead for your meals. )
Have a great trip.

Thanks that makes sense! I think we would just do CT but we also really want to do a winery day trip in Tuscany. Is there a way to do that from CT? Or best to be in Florence to do that?

What kind of winery day trip are you interested in? Does it have to be a Tuscan wine? You could look for one in Liguria, but you'll have to check into seasonal aspects as mentioned above. You will want to book early for August and be up early for hiking because of brutal heat, but at least you can jump in the sea in the afternoon!

Thanks valadelphia for the response. My husband really wants to do the typical vineyards in tuscany. Our intial plan was just to do tuscany and stay in florence as a base. Potentially do a vespa drive in the country side one day. However, our friends told us CT was gorgeous and we have to go. I am seeing many posts about how CT is very crowded so not sure if it's worth the travel time for this trip.