OT: Heading to Italy

dmchicago,  Based on ~ a dozen trips to Rome and Milan for work and a couple more to Italy for play, I'd recommend using a private driver as much as you can afford.  Both to get the most out of your time but also be as relaxed as possible.

My driver in Rome was the wonderful Walter Bellapadrona. 
http://www.taxiservicemontalcino.it/EN/contatti_taxi_autonoleggio_montalcino.html
but it looks like he's relocated his service to Montalcino. I met Walter when I literally walked into him walking out of a hotel.   He's totally sweet and an inherently cheerful person;  not common for a Roman.  He speaks very good English.   He ends his emails with "Big Kiss from Walter".  It's so Italian of him! :-)    He probably wouldn't do that if you are a guy. 

Use TripAdvisor to check reviews on private drivers, and negotiate big picture "OK how much for 2 full days wherever we want to go."  etc

Private drivers are especially valuable when you know you want to go to 3-4 different places in a city but aren't booked on a tour.   

7 random tips for you

1) One thing I started doing a couple years ago for the non-work days of trips across the pond: 
Had an alterations person customize my favorite vest.  She added to the inside of the vest,  4 pockets from the back pockets of 2 pair of boys cargo pants in a similar color. $10 from Target. ~ $50 for the alteration.  No one would think to pick pocket there, especially with a scarf.  A scarf dresses up any vest or outfit when traveling.

2) If a teenager or anyone carrying a baby approaches you asking for directions, that means you've probably been marked for pick pocketing and person #2 is nearby.
Handy phrase: 
Non toccare = don't touch   (simplest way to say it that gets the point across)

Mixing English and Italian works too.

"Non toccare or I will call Polizia di Stato on you right now."   (dial 113)
is usually intimidating enough.  ("Carabinieri" is more correct but harder to say when feeling emotional.)

3) You're be there well before the hottest part of the summer, but I found it handy to know: 
ghiaccio = ice 

I prefer well-iced drinks in summer vs lukewarm. 
I cheerfully acknowledge it's an American thing :-).
"sono americano. ho bisogno di ghiaccio"

Last time I tried that the server immediately replied, "no worries madame". Then, he demonstratively returned to the kitchen loudly talking to himself about the american who needed ice the entire way.  All in good fun :-). 

4) pronunciation note:
I was coached that thank you,  "grazie" , is pronounced [grazi-eh] . not [grazi]

5) A polite, simple-to-understand, yet direct way to preface your questions: 
"Is it possible..."
Is it possible to drive to _____ within 30 minutes? 
Is it possible to bring me 2 extra face cloths? 
Is it possible to do that before __:___ when I go to sleep? 

That seems to be 10x easier to understand than Could you___   or Would it be possible to ____

6) Google Drive docs keep me easily organized
doc naming is the trick
preface each doc with date and time
voila - your agenda forms automatically simply by sorting the folder by doc name
one folder per trip

yyyy mm dd tttt  event
2018 05 15 0800 Breakfast with ____ at _____
2018 05 15 1600 Train to Florence Platform ___  
2018 05 16 1000 Hotel Lobby meet driver

this makes each doc very short which is great for phone skimming in transit

Non event specific reference documents are named whatever 
"Rome evening fun - options" 
"Florence shopping"

7) Texas state pins
I bring 20 or so texas state pins to give to people who are especially nice - for them or to give to their kids. 
I explain that when they wear them, it will 1) Make them extra tough 
 2) Intimidate all New Yorkers, because Texans are tougher than New Yorkers ;-). 
https://www.pinmart.com/texas-state-shape-lapel-pin/

So Jealous. We were there just last year, but I can't wait to go back.
Wait til you get to Tuscany!
Enjoy!