Hello all and thank you in advance! We wanted to see if you guys had some thoughts on the itinerary as it is right now... been reading posts and some guidebooks but have the feeling that it needs some tweaking... any input is appreciated
Husband and I traveling, late 40s/30s, active, love outdoor activities/or just seeing landscapes, architecture, history (but selective with museums), hidden gems, adventures in general, live in Florida. Current itinerary:

Sat 6/2 Flight arrival to Venice from Nice at 13:25
Sun 6/3 Venice
Mon 6/4 19:25 train departure to Florence from Venice
Tue 6/5 Florence
Wed 6/6 Florence
Thu 6/7 Florence
Fri 6/8 Florence AM pick up car and thinking about heading to Pisa
Sat 6/9 San Gimignano & Siena
Sun 6/10 Montepulciano & Orvieto
Mon 6/11 Morning long drive to Pompeii and then head to Sorrento
Tue 6/12 Amalfi Coastal drive
Wed 6/13 Amalfi & Ravello (Return car this day)
Thu 6/14 Positano
Fri 6/15 Sorrento
Sat 6/16 AM ferry to Capri
Sun 6/17 AM ferry to Sorrento to catch train to Naples/Rome long travel day
Mon 6/18 Rome
Tue 6/19 Rome
Wed 6/20 Rome
Thu 6/21 11:40 flight out of Rome to Santorini

Initially we were thinking about heading to Florence in the morning of 6/5 instead, but because of hotel costs in Venice, we moved the departure to the night before. Also initially we were heading to Capri in the afternoon of 6/15 instead the following morning to have a full day, but seeing if this works better to lower hotel costs.
Still have to get the train tickets and finalize the car rental (have some questions about that but will post separately) We are both traveling with a 40L backpack as we are taking several low budget airline flights, so for ex in Pompeii thinking about just taking them with us and storing as per comments in other posts. Also, after reading various posts we see that many people advise against having a car in Amalfi Coast, but we love drives, sooo thought maybe we would brave it just for a day....
I have a feeling that we might be allocating a couple of days wrong... not sure if any of you would suggest shifting anything? Any input is appreciated.

Thank you!

Has your hotel In Venice agreed to store your luggage? If they can't or won't, you will have to lug it over the train station to store for the day.

Pisa is easier to visit from Florence by train as you don't have to figure out parking and avoiding ZTL.

I would take a day off Florence since you said you like outdoor activities and add that to Tuscany. You really haven't allowed enough time to visit the places in Tuscany you listed. I've stayed in Siena multiple times and still have things I want to see. Orvieto and Montepulciano deserve more time also.

I would not bother spending a night on Capri. Too much hassle changing hotels for one night. Parking will be a big issue on the Amalfi coast in June. You Amalfi itinerary doesn't make sense. To reach Amalfi from Sorrento, you drive past Positano yet you've listed it another day. I would cut a day from Amalfi coast or cut the Capri stay (visit it as a day trip by ferry from Sorrento) and add that day to Rome or Tuscany. Rome has a lot to see and so does Tuscany.

You don't want a car in Pisa on the Amalfi coast or on Capri.
You like to drive.... but do you like to sit in a stationary car? Look for car parks and get fined for getting it wrong.
BTW early June, good choice

Book train tickets way early for discounted fares at Acquista il biglietto con le nostre offerte - Trenitalia or www.italotreno.com - two competing rail companies using same tracks and stations and similar trains- www.seat61.com has loads of sage advice on doing that; general train info BETS-European Rail Experts and www.ricksteves.com.

All in all whole trip seems wonderfully planned.

It looks as if you are changing things to save money. IMHO, even if you like to drive, for much of your trip, a car is an expensive liability. Save the money on the car rental and use it for hotels and trains and arrange the trip for the best itinerary.
Unless you are really into Renaissance Art, you could cut a day from Florence or stay longer in Florence and take the train (very say) to Pisa and Lucca, and the bus to Sienna.

A car car would be nice for a few days in the Tuscan countryside.

By June, it will be pretty warm and traffic will be heavy on the AC, so a car is not a great choice. I would not use the bus either. Frankly, stuck looking out the window of a bus on the AC is not that great. Use the ferry. Being able to be outside, enjoying a breeze and seeing Positano and Capri, etc. from the open water is amazing!

Yeah consider dropping car in Orvieto and taking train to Rome and high-speed train to Naples or Salerno then train/ferries/bus via Sorrento or from Salerno ferries to Amalfi towns.

I too would just day trip to Capri - relocating for just a day is a waste of half a day for some.

Hello guys, thank you for the replies and input.

Took a day out of Florence, thank you and we decided for sure to have the car around Tuscany. We'll have 3 full days and I'm thinking we'll just have an idea of the places we'd like to see, but we'll just take it easy and enjoy the area and just see what we see.... we are going to be on the move for a while and this might be a good area to just be....

The feelings about the car are pretty unanimous in this forum so... we are considering dropping it in Tuscany.... you'll forgive us if perhaps we go the stubborn, try it ourselves route... we might, might just keep it for the first day in the Coast to at least have the chance to drive it if we are lucky and that day happens to be a good traffic day... I intend to work on a trip report when we get back so I'll let you guys know how that went if we end up going that way. We'll definitely drop it off at the beginning of the Coast part of the trip, so thank you for the ferry recommendations.

Regarding the Capri stay... so I am getting that you recommend either 2 nights or just a day trip no night stay right? Anybody heard of the anticomonasteroanacapri.com by any chance? Looking to see if I can find accommodation for 2 nights then.

Thank you for the Italo ref PalenQ... I got the Venice-FLorence ticket for 10Euros so that was a nice surprise!

Thank you very much

Are you staying in Sorrento or on the Amalfi coast? If on the coast, you need to make sure your hotel has parking (many don't). You need an IDP to drive in Italy. I suggest you spend some time learning signs (particularly the various ZTL signs). Pisa, Siena, San G, Montepulciano, Orvieto will all require parking outside ZTL. As for Pompeii, I would make sure no luggage is visible since you will have it with you.

trv3- wow can't beat that 10 euro price and folks should always also check Italo for fares too.

https://www.travelernick.com/2018/01/driving-in-italy/

I wouldn't say it covers everything but it'll give you some pointers. The car is useful in smaller centres that don't have good transit links. Especially the further south you go. But the big popular touristy cities? NO CAR!

I'd only use the car for the Tuscany part and train to Amalfi where cars are useless.