1st time planning an Italy trip

None of the four cities you mentioned are any place to be driving a car. All are congested, have many limited access areas, and a vehicle while visiting the city is useless. Each of those four cities deserves a stay, rather than trying to daytrip, I would say a minimum of 3 nights for each, Rome needs at least 4...so that is basically your two weeks. If you extend it to three, then maybe add in a smaller town for balance.

They do all have fast, modern train connections, making it a breeze to get from one to the other. Luggage on trains is easy, you carry it on. One thing you will want to plan for is to fit everything you need into a single smaller bag (carry-on size is ideal) with maybe a small day bag. Renting a car is expensive, you will need their insurance, gas is expensive, parking a hassle, and you would likely wind up getting some expensive tickets after you get home.

Get the Rick Steves Italy book, lots of good info on traveling in there, plus lots info on what to see.

Def get the RS Italy book and if you never been to Europe before, also get the RS EUROPE THROUGH THE BACK DOOR - it teaches you so much about trains, debit cards, credit cards, etc. Also, look here on the RS page under TRAVEL TIPS and read it all. His TRAVEL TIPS are so great.

For trains, seat61.com is a great site. Get train tickets 6 mo out for the best price.

Also, for Italy, it's always best to fly into Venice and out of Rome. The train will be fine. Look at the RS Venice, Florence, Rome tour for ideas. Do at least 3-4 nights in each of those cities (if not more). Fly into Venice, train to Florence with Day trips to Tuscany, train to Rome - then fly home. Or if you have 3 weeks, we love Sorrento as a base for the Amalfi coast -- then you could fly home from Naples if you add that. But Venice, Florence, Rome are a MUST.

For Florence, we did day trips into Tuscany with a company called WalkAboutFlorence -- we loved their BEST OF TUSCANY TOUR and their CHIANTI WINE AND FOOD SAFARI - it's a great way to see Tuscany without needing a car.

Also, download the FREE RS app on your phone BEFORE you go - there are tons of ITALY things on it - tons to learn and great walking tours, Cathedral tours, and a Grand Canal Tour on the Vaporetto around Venice. Get the RS pocket guide books and the ITALY BOOK, and EUROPE THROUGH THE BACK DOOR (sometimes cheaper on Amazon).

PS-- I live in Winston Salem -- we are neighbors.

In Nov, Rick Steves has a new IT guidebook coming out which is the 27th edition. I would hold off until then before investing in a guidebook. I wouldn’t be surprised if there was a 28th before your trip.
If you can, fly into Venice and out of Rome because the majority of flights departing Venice are at the crack of dawn and you would have to take a water taxi during the middle of the night which is expensive. If the flight departs Venice late morning, you can take a bus from Piazzale Roma to the Venice Airport that won’t break the bank.
You want a minimum of three nights to see Venice and if you add day trips i.e., Padua (30 minutes by direct train) and Vicenza (1h) add a day per trip. To look up train schedules use this link: https://www.trenitalia.com/en.html. The name of the train station in Venice is Venice S. Lucia.
From Venice take a train to Florence SM Novella (2h 15m) and stay there four nights and add a day trip to Siena (1h 15m by direct bus). You can also take day trips to Pisa (1h 30m) and Lucca (2h).
From Florence take a train to Rome (Roma) Termini station (1h 45m). I highly recommend sleeping in the Trastevere neighborhood. If not, sleep at the nearby Hotel Smeraldo. Stay in Rome a minimum of five nights and one day take the fast train to Naples (Central Naples train station [1h 15m]) for the day. Another good day trip option from Rome is Orvieto (1h 15m) and then ride the funicular to the top of the town.

You can always pick up the current Rick Steves book at your local library while awaiting a newer one to come out closer to your travel time. While you're at the library, grab the Rough Guide to Italy and/or Lonely Planet to supplement Rick.

Read a bunch to see what speaks to you. I wanted to alternate cities and more rural locales. When I did my 3-week run through Italy in 2015, I had a round trip flight in/out of Rome. My itinerary was Orvieto x 1 night, Sienna x 4 nights, Florence x 3 nights, Sirmione on Lake Garda* x 3 nights, Venice x 3 nights, Nocelle on the Amalfi Coast x 4 nights†, Rome x 3 nights.

*Contrarian lake choice

†I'm an airline geek, so wanted to fly a new airline on the trip -- took EasyJet from Venice to Naples and then went to Nocelle. Not for everyone -- but appealed to my personal travel likes.

Get a couple guide books at your public library. It doesn't matter if they are 2 or 5 years old, the main sights have been around for that many centuries, at least. This will give you a good idea of what there is to see and do in many places. Look for the DK Eyewitness Guides (in addition to Italy, they have in-depth guides for some cities). They have lots of photos so you'll get a good idea of what places and sights are likely to interest you. The problem most people have when planning a trip to Italy (whether it's the first or the 4th) is limiting themselves to a minimum number of places. So try to rank your choices by importance to you (and compare with each other) and assume that this is the first of several visits.

Public transportation is easy in Italy and cars are a real headache. Unless you are traveling with lots of suitcases, it's not a problem on trains. The cities you name are too far for day trips from each other, but they aren't long train journeys so you'd use less than 1/2 day each time you move.

Take a look a flight options. The best option is usually to fly non-stop but you may be too far from a major international hub to do that. Look at combinations with either a US connection or a European one. There are +s and -s to both.

Look at the Italy forum posts regularly and bookmark any that could help you.

Most important - Have fun planning.

Also check https://europeforvisitors.com/ for general information about Europe and for detailed information about Venice and Rome.

Hello All,
Thank you everyone for the information and advice it is Wonderful! I will share this with my friend and we will start making some wonderful plans. We do like the idea of flying into Venice and out of Rome it seems to be the main theme on flights. The advice to gather several guide books makes sense and we may limit our travel to just 2 or 3 areas and enjoy the sights there
Another trip could be in the future to see other locations!!
Again thank you all for the info and advice!!!!!
Katsinca

My first time to Europe, I read Europe Through The Back Door, as suggested above. Changed my travel life! So, I'm here to third or fourth that rec!

Thank you again for the info and advice!!! It gives me more things to plan for and with.
Thanks again!!!
Katsinca