Italy itinerary with Dolomites and Tuscany - Where to stay? Oct 12-21

Where to stay in Dolomites considering its in Oct? Driving to
Dolomites from Milan. Where to stay in the Tuscan area - Which are the
day trips I can do? WOuld love to try the food and the wine there.
Looking for three nights stay here. Can do 2 + 1 nights here.

This is a heck of a lot of driving! Where are you flying from? Will you be jet lagged?
How many NIGHTS do you actually have?

A 2 night stay is only one full day in location and you will spend so much time driving if you stick with your plan.

MXP to Ortisei (for example) is over 4 hours drive
Ortisei to a town in Tuscany probably 5 hour drive.

I would pick locations that are not so far flung on such a short trip.
If you have no interest in Milan- head to Florence by train on arrival- stay a night or 2, pick up car there and stay in a hill town for a few nights. (Siena, Montepulciano, Pienza)
Drop car and train to Rome for remainder.

If you drive- make sure all drivers have an IDP, read up on ZTLs, parking, speed cameras, etc.

8 days including the arrival day and the last three nights (2 days) in Rome gives you 6 days to tourist. You don't want to spend them driving and as noted by a previous commenter the Dolomites and Florence are in opposite directions. In October the Dolomite's mountain weather can be "variable." Weather.com has weather for European Cities too, It is rainy and 65 in Bolzano today for example. Head south this time and enjoy yourselves and you will come back. Milan on day 1, train to Florence on the morning of day 3 for days 3, 4 and 5, train to Rome of the morning of day 6 for your last two days. From Florence you can day trip to Siena easily, and/or book a wine tour. You DO NOT want to do a wine tour and be driving yourselves.

Thank you! I think we will stick to Milan, Tuscany and Rome then!
Does it make sense to include Cinque Terre in this itinerary?

I wouldn't add Cinque Terre. You'll be pressed for time to experience Tuscany and Rome fully as it is.

hey hey akshiajith
is trip this october (2 months away)? where are you flying from?
like all first timers to italy, you are planning too much without knowing the time it takes to travel by car/train/bus, finding places to park (IDP's are mandatory for each driver in italy, research that plus rules/laws/signage/ZTL's)
one of the top most countries to visit with crowds/busy with the places you want to see. it's high season all year long, 2days is 1 night, check-in is 2-4 pm, check-out 10-11am, your last day is about checking out, shower/breakfast/last minute packing/ transportation to airport & if back to USA is 3 hours for passport/immigration/ticket check in. any attraction/activity you're wanting/hoping book early. many things even hotels (budget in euros) have been booked months in advance.
hope all goes well, good luck and enjoy
aloha

Hey
Yes! the trip is this Oct 2025.
Im taking the train from Interlaken to Milan. Since Dolomites is clearly not a great choice, we are changing the itinerary to

a. Train to Milan. Stay in Milan for a night(1)
b. Drive to Siena. Stay for two nights (2)
c. Drive to Florence. Drop the car. Stay for 2 nights (2)
d. Train to Rome. Stay for 3 nights (3)
e. Fly out from Rome to India.

Would love to do a wine tour. Does it make sense to do this from Florence or Siena? We wanted to do one day trip Val d'Orcia from Siena. What else can we do in Siena?