Italy in November - 3 weeks by train

Bologna is a great 'little' city, and makes a really good base for an extended stay when planning day trips to Parma, Modena, Ferrara, Ravenna. If none of these places feature in your plans I would encourage you to keep Bologna for a future trip. Lucca would be my recommended substitute, allowing a morning visit to Pisa.

Orvieto would also be attractive for a 2 night stay if you were willing to take a night off Florence and Rome.

Cinque Terre and the Amalfi Coast are also better visited at another time during warmer weather.

Fly in to Milan - 1 night
1hr23min by train to Verona - 2 nights
1hr10min by train to Venice - 4 nights
1hr05min by train to Florence - 4 nights
1hr19min by train to Lucca - 2 nights
2hr56min by train to Siena - 2 nights
(via Pisa and Empoli)
2hr10min by train to Orvieto - 2 nights
(via Chiusi)
1hr21min by train to Rome - 4 nights
Fly out of Rome

Venice: take care of high tide. November is peak season for https://en.wikipedia.org/wiki/Acqua_alta

I've found the Acqua Alta to be an interesting experience in its own right. Street vendors will be out selling temporary wader overshoes so you can slosh around like a local.

Thank you for the suggestions very helpfull!

As we are traveling by train, i am more concerned not losing alot of time from moving in and out of hotels all the time and from one train to another.

I read that some people stay 1 week in Venice 1 week in Florence and 1 week in Rome. This seems like less moving but i am afraid that we will not see as much. I am confused as i have never been to Italy and don't know if its easy to move from one hotel to the other by trains and metro.

Does anyone have an idea if our plan will be very busy? As the most important thing for us is to have a great time...not only to see the most places...

We did a 3 week tour of Italy in November, 2012. We did see stay in Sorrento in early Nov, a day trip to Amalfi. The weather was actually fantastic for this part of the trip and there weren't many crowds. I don't know that you can depend on the weather being that nice. About the only thing we couldn't do was a trip to the top of the Mt Vesveous (sp?).

About a week later, the weather turned. We were staying in a little mountain town on the Lazio border, not far from Orvieto. That was the year Tuscany flooded, all are plans went up in the air. I think the Orvieto train station flooded. Any place we did have tickets to did do everything possible to accommodate us. If I had it to do over again I would have stayed in Rome instead of day tripping into it at this time of the year. Venice flooded badly that week as well, we were there the week after. St Mark's Square was empty. Nice to see it without the crowds but it was just a bit too quiet for me.

Loved Sienna, we only spent 1 night here, wish it was more.

Mary

I don't think your plan is too busy. Don't know if you need 5nights in Florence, might add an extra night in Milan. Take a bus from florence to sienna. And the fastest way to Rome was a bus back to Florence & catch a train from there.

Assisi we did as a day trip, it is another town I would like to go back to, if you have time.

I suspect that tolerance for a trip with a lot of 1-night and 2-night stops is a basic personality trait, one I lack. I don't know why I dislike having to change hotels, but I do. Day trips, even with 4 hours on trains and buses, don't bother me at all. Other folks really hate the extra time required for that round-trip to a place an hour or two away.

Aside from that, some people put a premium on seeing a lot of different places, whereas I resist leaving a city when I haven't accomplished some of my major goals there. It's a matter of priorities. From this trip you'll figure out your personal style of travel. You are tentatively planning long enough stays in some cities to allow a day-trip or two. Research those ahead of time but don't commit to them. If you're loving where you are and need a bit of down-time, stay put and do some casual wandering and café-sitting. If you're getting antsy, make one of the possible day-trips.

Having that type of flexibility may be useful in November, when the weather can be iffy.

Someone recommended this itinerary:
Milan - 1 night

I suppose you fly into Milan, one day is fine.

Verona - 2 nights
We visited Verona when driving through Italy and found one day was enough.

Venice - 4 nights

Venice is wonderful, but you can do a lot there in three days. Add one more day to Rome.

Lucca - 2 nights

Great little city, but can do it in half a day, also consider Pisa which is closely.

Siena - 2 nights
Agree

Florence - 4 nights
Agree, recommend the Hotel Balestri.
https://www.tripadvisor.com/Hotel_Review-g187895-d203902-Reviews-s1-Hotel_Balestri-Florence_Tuscany.html

Orvieto - 2 nights
Agree

Rome - 4 nights
Make it five nights. I have spend a week there twice and still have not seen what I wanted to see in Rome.

What are your interests? For instance, if you are huge fans of Renaissance art and architecture, 5 nights in Florence makes sense. If you aren't, it doesn't. As David said, Bologna is an excellent base for daytripping (because it is a major rail hub and easy to get to/from the train station once you're there), but not that much of a "destination" in an of itself. If you want to see a lot of places, spend 5 nights in Bologna. Head out early in the morning to a different town each day, wear yourselves out sightseeing, then relax on the train back, and have a leisurely dinner in Bologna - renowned for its food.

BTW Florence to Siena is best by bus. In Florence the bus and train are next to each other in the old city center, but in Siena the train station is an outlier and the bus isn't. Either way it's about an hour's ride.

I've been to Orvieto and loved it . . . in May, with long days and lots of sunshine. I'm not so sure I would enjoy it in November.

With regard to short stays of 1 and 2 nights, only you know what suits you best, taking into account your ability to easily manage yourself day to day when on the road.
I have a general policy I like to follow ...
One night stays are fine for trips less than 2 weeks.
Minimum stay of two night as a goal if your trip is 2-4 weeks.
Minimum stay of three night as a goal if your trip is over a month.

A few points ....
1. Choose your hotels close to the station when it has a central location. Otherwise make sure you are close to easy public transport.
2. Choose your train travel times wisely, so you minimise it eating into your sightseeing time. I prefer trains at lunch time (when shops can be closed) or early evening.
3. Don't unpack for 1 or 2 night stays. Wear the same thing on the second day if you can. This is easier to stick to in November than the heat of summer.
4. It's nice to spend evenings in different locations to experience regional food variations, for example. You get a 'feel' for more places overall than you may otherwise.
5. I love a new hotel room. If your staying in budget accommodation clean sheets and fresh towels are not a daily thing.
6. Some places lend themselves more easily to having a long term base and day tripping. This approach is better if your sights are radially spread out in different directions but within about 60mins of your chosen base by good public transport. If your locations can be strung together in a line or made to form a loop then my philosophy is that it's always best to keep moving on, and avoid possible backtracking.
As an example consider options for Milan, Verona and Venice.
(a) If you stop over in Verona then you only travel Milan>Verona>Venice.
(b) If you make Verona as a day trip from Venice then you travel Milan>Venice plus Venice>Verona plus Verona>Venice.
That's an extra 2.5 hours, plus time getting to/from station for the day trip. And of course you have additional fares to pay for.
7. I added the train times to the plan I suggested above. Note that only 2 days involve more than 90 minutes travelling, so you don't lose a large chunk of the day.