Two Week Trip Help with Itinerary please

If you can fly into Venice and out of Rome, do it. If not then fly into Milan and out of Rome.
Buy Rick Steves Best of Italy guidebook: https://store.ricksteves.com/shop/p/best-italy-guidebook so you can decide on where you go. You can then buy his Italy guidebook: https://store.ricksteves.com/shop/p/italy-guidebook that will teach you how to do it. Next summer a new edition will be available for the latter that I highly recommend buying. If you make reservations for a hotel from his 27th edition guidebook, don’t assume it’s also in his 28th edition. If it isn’t, make sure you tear out the pages in the 27th edition and bring them with you. This way you’ll have a map showing where your hotel is.

Hello and welcome!

For a first visit to Italy:

Fly in to Venice (easier to fly IN to Venice than out of)
Venice 3 nights
Train to Florence
Florence 3 nights
Pick up car
Tuscany hilltop of choice 4 nights ( this is your “relax” time)
Drop car
Train to Rome
Rome 4 nights

You’ll have to be willing to rent a car for the Tuscany portion

Could sub Lake Como/Varenna for Venice, in that case fly in to Milan

I think everyone should visit Venice -we love it!

Two years ago we did the following itinerary in October. We were lucky with absolutely fantastic weather, we did all of it by public transit. We started and ended in Rome as that it where we can get direct flights. If you can end in Milan that would be perfect.

We hadn't been to Rome for many years so wanted lots of time.

Rome 3 nights, stayed sort of NE side Borghese gardens
Orvieto 2 nights
Siena 2 nights
Lucca 2 nights
Cinque Terre 3 nights
Rome 2 nights- stayed on SW side
If I did it again now I would probably go straight to Orvieto and give myself an extra night in either Siena or Lucca to cut down on 2 night stays.

I'd go as late in the year as possible, to avoid the crowds and the heat.

Venice is at the top of my list of favorite cities in the world. It's a very good place to start because it's easy to soak up the atmosphere, the charm and the beauty while getting over jetlag. Rome is a noisy, bustling city with major impressive sights and can be overwhelming and confusing. Venice is laid back, quiet and slow (except for the possible crush of tourists at the really busiest spots.

Florence is a Renaissance art lover's paradise. It's also a good place for daytrips.

Bologna is quieter with fewer tourists and a foodie's paradise (I'm told ). It has a few sights worth seeing and an attractive historic center. The big plus for a stay here is that as a rail hub there are lots of good day trips to small towns.