When to go to Italy and Where to stay for several weeks? Planning stages

We love Late Sept and Oct in Italy, less crowds, not as HOT.

I'd fly into Venice and start there - it's a great place to recoup after a flight and it's such a unique town.

For day trips out of Florence - we loved a company called WalkAbout Florence - we did two trips with them - THE BEST OF TUSCANY TOUR and THE CHIANTI WINE & FOOD SAFARI TOUR. The Rick Steves book has lots of recommendations too.
Sorrento is another relaxing town with amazing food and easy day trips to the Amalfi Coast with SharedTours.com.
It's also an easy train trip to Herculaneum which we like better than Pompeii.

Italy is our favorite European country and we hope to do what you are doing when we retire.

Unless you want to jump through all the hoops required to obtain a long-stay visa, you'll ned to keep the trip to no more than 90 days because of the Schengen-zone limit of 90 days within any rolling 180-day [corrected] period. Overstaying that limit can result in a substantial fine and being banned from returning for years.

I'd decide about the timing of the trip after deciding on the key places I wanted to go. There'd be nothing wrong with a sumer trip if you wanted to spend all your time hiking in the Dolomites.

We have been to Italy many times and have had the best weather in the fall.
Take a look at the Piedmont near Alba and Puglia; our base was Polignano a Mare.. They couldn’t be more different.
We also loved the Dolomites; we based in Ortisei.
We have spent a lot of time in all the Italian lakes too, mostly in Bellagio on Lake Como. We also have enjoyed Lake Maggiore and Lake Garda, not Lake Orta so much.

We loved almost every month when we lived in Italy except July and August. Those are tolerable if you are high in the mountains.

A few quick thoughts on timing.

March-May are lovely if you think about moving south to north, but the Dolomites are not really a great option unless you want to hit ski season, which ends at Easter. It is also off season in Puglia but that can be nice if you are not looking for a beach scene. The Amalfi Coast, in my opinion, is best in spring and Rome is delightful.

On the other end of the spectrum, Sept-Nov moving north to south is nice. The Dolomites are great although many of the lifts close for ‘tween seasons by the end of September (depending on exactly where you would go). The later in the autumn the better for Rome, IMO. You can experience it more as a temporary local.

Thank you to everyone for your responses. I have some places I have not considered to research and I like the idea of traveling in the fall - north to south.

Mid-February to mid-May. Weather is generally mild and sunny. With that long, some rainy days won't be a big downer. Fall sounds nice but September is still high season and summer weather and days are short in November and December.

I could happily spend a week in Venice, a week in Salerno, a week in Naples. If you rent a car (leasing might be a good option), Tuscany and Umbria for 2-3 weeks (be ready for frustration with a car, but overall well worth it). Without a car, at least a week in Bologna - so many easy day trips by train.

I like spring to late spring because days are longer. Mid June through mid September is generally scorching hot, unless in the mountains. Mid November through Early March is kind of cold, so not ideal for a beach bum.

Ha. We live 45 minutes from the Gulf of Mexico. While the Mediterranean is beautiful and we are looking at exploring the Amalfi Coast, I am spoiled by the sugar white sand beaches near home.

Again, I truly appreciate everyone’s input. I am mindful of the Schengen Zone and it’s restrictions to our planning (thank you for the heads up), but hopefully we are able to obtain Italian passports due to my husband’s Italian ancestry. Grazie!

You may want to do some research on the passport issue. Depending on where you live in the US, passport applications are taking between 2 and 5 years to process.