8 nights - November - starting in Milan - help

I plan every trip by writing it out day by day, so that would be too many stops for me, but there are some things that are not clear about your proposed plan:
Are you planning to spend any time in Milan?
Are you looking to spend time in Florence as well as in another location in Tuscany?
With your timeline, I would spend it all on a lake and in Venice, no car needed.

It is aggressive and could easily be done by trsin

The only place a car is useful is Tuscany
It will just be an expensive headache in Milan, Venice and Florence

I would drop Lake Como for sure-not at its best in November

For 8 nights pick no more than 3 locations
Since you have to end in Milan consider taking train to Florence on arrival

Florence 3 nights
Pick up car
Tuscany hill town of choice 3 nights
Return car and train to Milan for 2 nights

A 3 night stay is only 2 full days in a location
Each location change eats up at least half a day

Thank you for your reply. Honestly, all we have is arriving on November 8th. We are open to any and all suggestions. We are more interested in getting outside of Milan into the beauty of Italy (not to say Milan is not fabulous). That being said, we are perfectly fine with arriving and stopping off in Milan, and moving on to next location. I know that was an aggressive itinerary, but we can certainly cross of a few and focus on the top! Again, any help would be great.

Make a list of your priorities from the list and we can help you arrange them. No more than 2-3 stops in 8 days would be my general guide. They are all good options--though I take Christine's good info that the lakes are not ideal in November.
If you are not interested in Milan, don't feel bad if you skip it. You can depart on the train on arrival to your farthest location and work your way back. If your flight out is early morning, then you can spend a night in Milan, easy peasy.

Lastly, might I add, my husband would love to visit Venice and take a gondola. I just don't know how realistic that is in November as I've said to him. Feedback on this too appreciated.

If you are departing from Milan ( i presume MXP) then you need to stay in Milan night before departure
So that’s one night gone at least and if Milan is not priority it makes sense to move on immediately by train to your chosen first destination-could be Venice or Florence-both are easy via fast train

Driving after an overnight flight is very unwise

All drivers will need an IDP-required by law
Read up on ZTLs, parking, speed cameras etc

Is this aggressive? 4 cities plus an entire region in 8 nights? Yeah, I'd call that aggressive. Renting a car? Why? Have you driven in Europe before? Do you have your IDP? Do your hotels (unlike the majority) have inexpensive parking near them? Do you know how to avoid ZTLs? And are you aware that you can't drive a car in Venice? Trains between cities will be a much easier way of getting around. The only time, on your proposed itinerary, that a car would be an asset is for any visits to the more remote Tuscan hill towns. I think you have greatly underestimated the travel time needed between each place you want to visit. As it is, your trip will see transit time almost equal the time you will have to actually experience these places.

You need to eliminate at least one, possibly 2 places. Make a list of what you want to see and do in each location. That should inform the decision on how many days you need in each. Then factor in a loss of half a day each time you change hotels. And dont forget that you need to be back in Milan the night before you fly home. Finally, eliminate those places with the lowest priority, until you reach a manageable itinerary. I agree with the others that Lake Como is probably not the best choice for a November visit. And if your husband wants a gondola ride in Venice, then just do it on a day without rain.

RE Venice in November: I consider Venice a year-round destination--go when you can because it won't always be there. If you experience aqua alta, that's Venice. If you luck out and have only perfect weather, then you have experienced something special. If you google "Venice in November" you will see lots of arguments in favor.

We'd like to drive. What are your thoughts on the following:

11/8/25 Arrive in Milan in morning
11/9/25 Arrive in Venice (two nights?)
11/11/25 Arrive Florence (two nights?)
11/13/25 Arrive Tuscany (two nights?)
11/15/25 drive back to Milan
11/16/25 Depart for JFK

People have freely given their time to help you, so I hope you will do some deep diving into this thread before deciding anything, best of luck!

BTW - I just saw all your posts. Thank you. It sounds like the train is the way to go, and maybe Eliminate Tuscany. I have been reading about the zones and understand that is clearly a deterrence for driving. I sent an itinerary and any comments I will take.

You can buy yourself some time by skipping at least one of the nights in Milan, but more time in each place is really rewarding. Two nights is just one day--getting from place to place takes time so you do not necessarily see "more."
Some people would spend the entire week in Venice and few would bat an eye at that--just something to think about.

You can add a night in Florence and take a day trip to Siena by direct bus for the day. The bus takes 1h 15m and drops you off in the city center. The train takes longer and drops you off further away from the center.

I agree with Valadelphia. Venice is only 2.5 hours by high-speed train from Milan’s central train station. Seasoned travelers know since it’s wise to be in the city of your return flight the night before that flight— it will make the best use of your time to head for Venice ( or Florence) immediately after arriving in Italy,

The fastest high-speed trains travel from Venice to Florence in 2:15; Florence to Milan in 2:00.

Time permitting, Padua— just 25 minutes by train—is a great town to visit from Venice. And Siena. as mentioned by MaryPat, is a great destination to visit from Florence.

11/8/25 Arrive in Milan in morning
11/9/25 Arrive in Venice (two nights?)
11/11/25 Arrive Florence (two nights?)
11/13/25 Arrive Tuscany (two nights?)
11/15/25 drive back to Milan
11/16/25 Depart for JFK

Glad to see you gave up the notion of driving. But even with the train, between leaving one hotel and checking into the next one, you still lose almost half a day. Certainly a whole morning. So 2 nights is only 1 1/2 days. Heading straight to Venice after arriving in Milan will reward you with more sight seeing time in Venice (3 nights). I'd scrap Tuscany as a separate stay. Tuscany isn't a town or city. It's an entire region. Spend 4 nights in Florence. Spend one or 2 days visiting Tuscan towns as day trips. Pisa, Lucca, and Siena are just a few options. Then go to Milan for your last night.

I don't know where you live, in terms of possible options at an airport, but, why not fly into Venice and home from Florence?

Great Big Thank you to everyone! Just read the last two posts from CJean and Jules M..... Love the idea of flying into Venice and flying out of Florence.... Thailand was easier planning than this trip. I couldn't get this trip into an organized thought. First time on this website (and will use going forward), however, are there also hotel recommendations to b found in the forums?

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