Milan to Lake Como or Beach town and Tuscany itinerary

Where will you be departing from?

Before you settle on Lake Como you might want to read this:
https://community.ricksteves.com/travel-forum/italy/is-lake-como-getting-crowded-like-the-ct-and-ac

If you choose Tuscany you will need a car

We will also depart from Milan

*1) Is the daughter included in the count above--do you have 5 or 6? Five will be tight in a large car (or my preference, a small SUV), but if you are 6, I would nix that entirely and do a public transport itinerary.
I like to do the longer travel at the start of the trip and if flying out of Milan, you may want to put lake time at the end. Your daughter could meet you in Florence as well.

I agree with above- 6 will need a van and that's a pain to drive, parking will be an issue everywhere.
If 5 adults it will be tight- most rentals have very limited trunk space.

OK--I would normally say move on to Florence and meet there instead (put Milan at end because you'll need to be there night before departure) but with your flight arriving at 5 pm you won't reach Florence til probably 10 pm. That won't be a problem checking in most hotels but could be a problem if you plan to rent apartment.

Can your daughter stay in Bologna and meet you in Florence the next am? It's a shame to waste that first night in Milan but that might be what you will need to do.

How many NIGHTS do you actually have on the ground in Italy? What time is departure flight?
What are your dates? Car pick up/drop off will be be an issue on weekends, museums closed on Monday, etc)

If you can all meet in Florence on arrival night (or next morning) -stay there 3 nights. Pick up car as you leave and stay somewhere outside Siena or Montepulciano- lots of agriturismos in the area that would suit your needs. Stay there another 4 nights. (some do require longer stays)

Drop the car when done in Tuscany- (Florence drop off) and take a look at Stresa on Lake Maggiore. 3 nights there. Way less crowded than Como and you can stay there the night before flight departure from MXP- there is a direct bus to airport.

The only "beachy" sort of place would be Cinque Terre and I would avoid that like the plague! The crowds are simply overwhelming.

Good catch from Christine on your arrival time. What month will the trip occur?
As far as lakes-Tuscany-coast, does your group have a consensus? You have some logistical things to sort out first, but happy to make some coastal suggestions once we confirm the number for the driving plan. You would be about two hours from the coast at Siena, so it would have to be a separate stay, and your ten days are getting crowded...
Montelpulciano to my favorite piece of coast (Maremma park) is about an hour and a half, but once there you can bike/hike to a stunning natural beach.

Great questions! We arrive on Friday at 5:00 in Milan. My daughter is included in the 5.

-After reading the previous posts about Como, I think we are scratching that.

-We do not want to stay in Florence, rather a smaller town like Sienna or Montepulciano or Cortona.

-We do not mind driving 2 hours (4 hours roundtrip) for a day trip. We live in NC and drive 2 hours to the mountains routinely for hiking.
-Would love to know where to base in Tuscany, and any beach towns to either day trip or to overnight at. We really just love nature and either lakes or beaches we would be great!
-We fly out the following Monday at 7:30, so will have to be in Milan that Sunday.

Thank you all so much for your advice!

Sounds good--perhaps two bases in Tuscany (interior and coast) and the last night in Milan sounds nice.
I have stayed in Massa Marittima and Campiglia Marittima, both are cute towns within spitting distance of the coast if you want to try to "best of both worlds" it.
I like the beaches around Baratti/Populonia--a pretty sandy bay and some rocky spots you can take a satisfying hike to (Buca delle Fate). Further south, Cala Violina is a beach worth a hike. The Maremma park is probably about as far south as you'd want to go, but just 30 minutes south of there is Orbetello with sandy beaches on spits connecting the mainland to the promontory and rocky beaches on Monte Argentario. {Note there are plenty of other beaches along here, but I am listing the ones I have been to or that I know to be especially scenic and worth making an effort for}
I guess at this point I'd be searching the agriturismi to see what looks appealing for your family and take it from there, good luck!

You have 10 NIGHTS in Italy.
One night must be spent in Milan or at MXP at the end.
One night is arrival night- I think you are going to have to stay in Milan- not a good idea to try to drive to Tuscany from Milan at night.
Or maybe get to Bologna and meet your daughter there?
Since you don't want to stay in Florence, no need to pass through there just to get to Tuscany.

If you meet up in Bologna I'd just pick up the car there and drive to Tuscany. I would NOT want to drive in or out or around Milan.

That leaves 8 NIGHTS.
Sounds like Tuscany countryside is a must- give that 5 nights- will allow for several day trips and a nice long stay at an agritursimo. With a car you will want to be staying outside of the town walls- parking inside, driving in and out of any of the towns you list is just difficult, sometimes impossible. We love the Val D'Orcia area near Pienza. Choose an agritursimo that provides dinner or you will have to figure out where to eat and drive/park every evening. A pool should be a must in the summer. Many agriturismos have cooking classes as well.
Agriturismo site https://en.agriturismo.it
Booking.com is a good place to start looking.

From there I don't think I would want to venture quite as far as Maremma- although I know it must be beautiful (I'v been researching that area for a future trip).
You need to start working your way back north to Milan at some point.

The Ligurian coast is lovely- good train access as well so you can drop the car as you head north from Tuscany- (La Spezia or Pisa work)
Look at Chiavari, Rapallo, Santa Margherita Liguria. They are all popular with Italian vacationers. We loved S M Liguria.
3 nights in one of those towns would be perfect. There are ferries up and own the coast, hiking trails, etc
It's an easy train ride to Milan for your last night.

Do your homework on driving in Italy. Tuscany area is easy but you still need to be aware of ZTLs, speed cameras, parking etc.
All drivers must have an IDP- get at your local AAA.

You might also read a bit about what the beaches are like in Italy. Nothing at all like beaches in NC ;)

hey hey heatherandmarksmith
so many things to think about with your gang and 10 days to decide where. you have received different responses what you can do and look for. don't try to cram in so much at once and spend more time driving than enjoying to sit and relax. tell them all to pack light, it will be hot, you may find a place with a washer (i bring a small container of liquid laundry detergent if i have to hand wash in sink)
many people traveling want to see the "american dream" lake como & tuscany. glad you scratched lake como with there being couple other lakes to enjoy. sending you my 2 cents of places to check out with your gang and near milan, lake garda
campingspiaggiadoro.com
laroccacamp.com
campingsanfrancesco.com
camping-serenella.it
different accomodations for everyone, activities, pool/beach/hiking/restaurant/store/parking on property situated at bottom of lake near train transportation.
we stayed in bardolino several years ago for their annual wine festival "festa dell uva", loved it. the lake is gorgeous with mountain views, ferries, other small towns/villages
thecrowdedplanet.com/ things to do on lake garda
gardavisit.it
check the different categories the lake offers
other posters have mentioned stresa on lake maggiore here. there's a poster on forum named Karen that lived in verbania couple years and moved back to monterey california, hoping she'll pop up
discovernorthernitaly.com
10 most beautiful towns on lake maggiore or 15 can't miss things on the lake.
just some ideas to rattle your brain some :) enjoy and have fun. keep asking questions, here to help you and not be stressed
aloha