Revised itinerary advise

Unless you arrive late in the day in Milan, why not go on to Varenna on arrival day?

You may want to consider a visit to Ostia Antica vs the mad dash day trip from Rome to Pompeii

I don’t know why I didn’t think to go to Varenna on arrival day other than my brain is fried haha

Certainly good advice, unless an afternoon in Milan is worth it. There is nothing major I am dying to see there. The Opera and Last Supper would be nice, but not what we would consider “mandatory”. I don’t know how useful we will be after the flight anyway!

H is much better with jetlag than I am. I may have passed out on our bed in Paris upon arrival last time we were abroad ;)

It’s easy to take the bus from Florence to Siena, and the bus will leave you off in the historical area. The bus station in Florence is very close to the main SM Novella train station. It would be nice to see a smaller city during your time there, too, and Siena is a wonderful town.

I live near Seattle and agree that I would stay the first night at Varenna at Lake Como. We’ve taken the train from Malpensa into Milano Centrale train station and up to Lake Como. The nice thing about heading there Day 1 is that you won’t need to pack up that next morning when you’re tired and then head up to the lake. Relaxing next to the lake with breakfast is a much better alternative! ; )

I agree - since it looks like you aren't very interested in Milan, skip it. Use the extra night somewhere else.

Can't comment on Milan and Varenna

Venice, Florence, Rome looks good.

I think Pompeii is too far for a day trip- it's a huge sight.
Sure it can be done but it will be exhausting and you've only got 4 nights/3 days in Rome as it is.

Day trip by bus to Siena would be perfect.

Train to Florence, stay 3 nights

Three nights translates into 2 days. That's not enough time to add any side trips. Spend the entire two days in Florence.