Tuscany travel recommendations

If you're leaning towards 5 nights in Florence, then do that. A day trip to Siena is definitely doable, and I'd recommend going there. Siena is lovely. But, Orvieto is very nice too. That would be a longer day trip from Florence as it's closer to Rome. Maybe visit Orvieto as a day trip from Rome if you have time.
Full disclosure: I love Florence and would always recommend staying there as long as possible!
Have a wonderful time!

I have options with the nights, and can stay completely in Florence. Then visit the countryside during the day. Was not planning to rent a car but not opposed to it. Or, we can continue with the 3 night Florence stay, and change the small town experience to Sienna, or another town more located in the Tuscany country side.

You are not overthinking. Careful planning will help get the most out of your trip.

Staying in Florence and visiting the countryside by renting a car is not very feasible. Driving in Florence is hard. ZTLs complicate matters. Even though the distances don't seem great, getting past the outskirts of Florence and into the countryside will eat up 45 minutes to an hour each way. We did the opposite, we stayed in the countryside and took a commuter bus into Florence.

While I love Siena, I regard it as a medium sized town more like Florence than the small Tuscan villages we visited. You won't get a small town experience in Siena like you would in Radda, San Gimignano, Montepulciano, Volterra or Castellina. I suggest you stay in Florence and take a bus tour of the hillside towns of San Gimignano and Volterra.

Also, sit down and do a complete itinerary, including travel time. Lots of first time travelers forget to add in travel and find they have a lot less time at their destinations than they thought. For instance, you list 3 nights in Florence in your original itinerary. That's only 2 days. Does the 18 nights you mention include the arrival and departure days? That's 2 days gone right there.

Finally, for a trip that long, you should schedule in at least one or two "down" days, where there's nothing on your calendar. That will allow you to experience the unexpected. Some of our most rewarding experiences were completely unplanned and unexpected. Having a little flexibility made it possible.

Happy travels!

Thanks for the quick responses. I am leaning toward the 5 night stay in Florence and visiting the countryside from there. Why add other relocation days if not necessary. On a side note the Naples and Positano locations i cannot change due to free lodging. we planned to squeeze Pompeii and Capri into the 2 night Naples stay and then relax in Positano. Capri is always an option out of Positano I guess. Then we would train from Salerno to Rome..

From Naples to Capri is an easy ferry ride.
We love Siena but it is a small city. Drive historic Rt.222,the Chiantigianna , through the lovely small towns in the Chianti region. We have stayed in Panzano and Castellina several times.
Orvieto can be crowded with day trippers as it is just off the Autostrada from Rome as well as on the main train line. It is lovely though, has a beautiful cathedral, and is in Umbria.

As much as I don’t like “one night stands”, I would spend 4 nights in Florence and 1 in Orvieto. The little city has a great night-time vibe and lack of day trippers. Since you are locked in to Naples and Positano, I would visit Capri from Positano rather than using your short time in Naples to visit Capri. Naples is a large city with great museums and views of the Bay of Naples, Capri, Vesuvius and the city from Castel Sant’Elmo are outstanding. I think in using it as a jump off point to see Pompeii and Capri, many people don’t see the treasures and charm of Naples.

anywhere u go is great in Italy ... you'll go back !!!! ... been to Como .. now prefer the largest lake in Italy ---> Lake Garda ... 31 miles high .. 10 miles wide at the bottom .. narrower as you sail/drive north ..pituresque towns dot the lake (bike,bus,sail,even hang-glide from the mountain to the shore below) we'll be able to go there hopefully in Sept. ... they have a huge 5 day winefest in Bardolino on the eastern prominade/shoreline .. starts with a parade and ends with fireworks on the lake ... they have a smaller 2day winefest in May but you'll need to look that up .... we're staying 5 days this time in the largest town at the bottom which is "Desenzano" ..... OH .... "Gubbio" is having their huge candle festival which is always on May 15th .. an all day affair ... .. 3 neighborhoods compete ... all wear their own colored outfits/scarfs .. 3 different colors etc. ... bands go through the neighborhoods during the day (They all have breakfast at another location before it starts) then those 800lb candles come out of the lower church and end up on the mountain in another church .. (take the bird cage lift up during the day before and go in the church .. later u are not allowed) .. they run through the neighborhoods carrying the candles during the day then rest them on stands then pick up the pace later and every 150' they change hands as their so heavy ... in the evening they go as fast as they can up the mountain .. after they hang out and party in their neighborhoods ALL night .. if u purchase a colored scarf and your in their neighborhood u could get invited in for a drink in the pub or their house ... fun fun fun ... we'll go back

flying in and out of? Sienna ----> worlds first bank ... Palio twice a year ... James bond filmed here .... Churches Marble floors took like 300? years to finish ... Youtube ----> Sienna Cathedral Tour ...... Lucca isn't far from Florence ... rent a bike and ride around the walled city (3+ miles).. Orvieto ----> Prettiest church Facade + St.Patricks Well a must do .. took 10 years ... double helix ramps ... while your going down another ramp under yours (donkeys hauled water) is coming up ... not far -----> Youtube ----> Civita di Bagnoregio .... almost a ghostown .. 6 residents? great visual in person ..... we prefer the largest lake ... Lake Garda ... many towns with many options there ... huge mountains surround the northern 2/3rds (31miles to the top) ... returning there in Sept. for the 5 day winefest ... enjoy your schedule

Just curious-has anyone rented a car at Florence airport, driven somewhere else, and returned it to the Florence airport without ever taking the car into Florence?