Italy in September

In that time frame my choice would be to fly into Florence, spend about 4 days there, take the fast train to Rome, 3 days there and then take the train to Sorrento and choose a city on the amalfi coast and do 3 days there.

Skip Venice and Naples.

I’ll be there.

September 12-28.

Two nights in Lake Como
Four nights in Alba (Piedmonte region)
Four nights in Greve in Chianti (Tuscany)
Three nights on the Isle of Capri
Two nights in Madrid, Spain on the way home.

Can’t wait.

Get a private tour for the Vatican. I used Dark Rome.

Venice is only worth one day. There's no locals still living there. It's like Disney. You can skip Naples. Go down to Sicily and check out Palermo which has the best street food in Europe. Then there's some
Amazing beaches, and the most beautiful women in the world.

Lake Como

Italy was overrun with communists in the 1940s.

Don’t support a communist country.

Went in September this past year for 2 weeks. Loved it. I wouldn't go back to Venice, and wish I hadn't wasted time there.

Rome, Tuscany hill towns, and Cinque Terre were our favorite. Hiking between the towns in Cinque Terre was my personal favorite day, and the most beautiful hiking I have ever done.

We are in Alba to explore the Piedmonte regions towns and vineyards. We’re all into wine in a big way. It’s a group of twelve. Literally only there for wine and food.

We’re staying in Bellagio.

ETA: We aren't staying in the town of Alba. We're staying at an Agritourismo at a vineyard a few miles from the town. We'll be planning to visit 2-3 vineyards/enotecas a day and eating leisurally lunches and dinners. This group travels together frequently. I expect that we'll all have a fair amount of wine shipped back as we will also spend several days in Tuscany (Gaoile in Chianti) and do the same. We've done this before in the Tuscan countryside and enjoy the relaxed pace and enjoying the history of the small towns of Italy.

I think we'll be ahead of the white truffle festivals and hunts by about a month or so but we should be in both regions around the time of the wine harvests and harvest festivals depending on the summer weather in the regions this year.

Returning to this thread to encourage you NOT to take a packaged tour unless you have mobility issues (ie, can’t walk long distances, carry your own small suitcase) or other physical limitations, or are/are traveling with extremely anxious travelers. You can see and do so much more on your own, without being locked into itineraries with groups. Do you really want to sit on a bus, gazing out the window at things, getting up every morning at the crack of dawn to have your luggage loaded on the bus, never getting to sleep in, stay out late, or choose your own restaurants?

You mention the Vatican: if religious tourism is your focus, consider staying at a religious guest house/convent/monastery. Monasterystays.com has listings all over Europe, with many, many in Italy & specifically Rome. Also of potential interest is a Scavi tour: the first-century excavations beneath St. Peter’s.....the purported actual tomb of St Peter in the ancient Roman cemetery that once topped the Vatican hill. You must request the tour pretty far in advance, and only ~60 or so people are admitted each day. When you request, give a range of available dates and you will stand a better chance of getting the tour. I’m non-religious, yet it was an amazingly moving experience to descend beneath the basilica into the ancient foundations of the faith. Here’s a link to the office of the Scavi’s website, where you can email your tour request: LINK. You have to send the request yourself; it’s not something you will experience with a package tour company.

With just 8-10 days, I’d focus on Rome & Florence, with perhaps a smaller town or countryside visit between the two. You could easily fill 4-5 days in Rome (either at a leisurely pace or a jam packed one, depending on how much you like art, ancient history, or religious sites). A train to Florence is easy, quick, and not expensive; but Florence offers an abundance of art as well. Some quickly tire of looking-looking-looking, so it can be nice to add a smaller town like Montepulciano or Orvieto between the two; or even a stay at someplace like San Casciano dei Bagni (thermal baths, spas, etc) for a completely different feeling.

When you make the effort to do the planning yourself, it can be YOUR vacation; not a rote shuffle through someone else’s itinerary, insluated from locals and ultimately learning more about your tour compatriots than about Italy or Italians.

The only tours we take are walking tours in a city and that's generally for museums or something like The Vatican. Other than that we're on our own and that's how we like it.