First time in Italy seeking itinerary advice

That’s a lovely plan!

Bella - train to Milan then change to Bellano
Because of the travel time I might give that location 3 nights-2 days-take 1 from Florence or Rome?
With 4 full days in Florence you could do a day trip to other Tuscan hill towns if you wish

2 nights in SIENA is perfect and you can never have enough time in Rome

Bus is best from Florence to Siena as it will drop you up in town, rather than down the hill at train station.
From Siena the easiest way to Rome is by bus, otherwise it’s train back to Florence then change to train to Rome

Overall it’s a really good first itinerary !

As ChristineH says, there’s never too much time in Rome.

For Sienna in 2022, we had a night and parts of two days, and could’ve used more, if our schedule had allowed. At the train station, there was a long line for getting a taxi into the old town, but no taxis were showing up. We found the bus stop, down an unmarked elevator below the mall across from the train station, but that was a hit-and-miss attempt to get into town. Rick Steves’ guidebook gives some hints at finding the bus stop, but it wasn’t obvious. Once on the bus, it immediately took off before we could get seated, and trying to control the rolling suitcases as the bus whipped around hairpin curves heading uphill was a challenge. A taxi back to the train station the next afternoon was easy to get, and it was a much less adventurous ride. Still wish we’d had 2 nights in Sienna … next time.

We just got back from Italy. Everyone has different experiences and a different take on things. I would perhaps suggest you may not need 4 days in Venice. We were there 1 day and night and that was plenty for us. We loved Bologna which is another alternative you may consider that is close by.
We also went to Ortesei from Venice which was a bit of journey but WELL worth it!! :) It was GOREGOUS!

When you are in Rome, you might want to plan to take a day trip to Caserta. It’s an hour by train if you take the direct Frecciarossa (Trenitalia) train. It will give you a different experience from the rest of your nice itinerary.

The train station is in front of the expansive Reggio di Caserta (royal palace). Be sure to take the golf cart shuttle out to the end of the massive gardens, plus it will take you through some of the forest paths. Buy your tickets on-line ahead of time. The tickets are timed entry.

https://reggiadicaserta.cultura.gov.it/en/

Venice is our favorite city in Italy. Hope you enjoy it, too!

It looks pretty darn good to me. Don't think I'd change a thing. Enjoy!

I like the time allocation, too, but I believe you've miscounted your days in Rome. It looks Iike 4 days rather than 5. Neither is too many. There's always more to see in Rome, especially if you enjoy gorgeous churches.

I just came back from covering northern Italy and spent two-and-a-half days in Venice so three days should be plenty. Four days is plenty for Florence if you're able to get out of the city. Five in Rome itself is too much, unless you will use one or two days to see things outside the city. I spent three days in Rome last September then another few days in Pompeii, stayed in Sorrento and did the Amalfi Coast. Did you consider seeing the Cinque Terre? As far as Lake Como, I suggest staying in Varenna or Tremezzo. I stayed in Tremezzo just across from Bellagio and I thought it was a better location than the Bellagio side. Better views of the mountains over the lake. All the action and things to see are down in this area so Bellano may be too far north. It's good you're going in October. Italy is very warm and humid during summer. You'll have fewer crowds, too. Have you thought of renting a car for your trip? An added expense but you'll have more flexibility. It's easy to rent one and the roads are good. Lots of tolls, though.

I love Venice, and there's always a day trip to Padua. Keep the schedule as is. You never know when your flight is delayed or canceled and you lose the first day . It's happened to us a few times. Enjoy!

I agree with those who said it is best to take the bus from Florence to Siena. It drops you off in the central part of the city.

I want to comment on your plan for Bellano. Bellano is one train stop north of Varenna, just about 7 minutes by train, if that. I will say that Bellano is flatter than either Varenna or Bellagio. If mobility is an issue, that is important. If you want a village that is flatter than Varenna or Bellagio, look into Mennagio. The town had a cute town square and a very, very lovely lakefront promenade.

Also, Bellano has much less frequent ferry service to other lake towns. You would have to watch your schedule carefully to time the ferry. Otherwise, you have to take the train to Varenna for more frequent ferry service.

Bellano did not have much appeal to me. I went for a day in April, riding the train there from Varenna, in order to visit the Orrido gorge. I had lunch, sadly I missed a morning market.