Almafi vs Cinque Terre

We could give better answers if we knew the full itinerary - for example, whether you are flying out of Milan as well. It's not even clear if your itinerary is INTENDED to include both the AC and CT (which some of us think is overkill), or if you are just casting around the Milan area for things to do with jet lag. Maybe you are referring to some past posts, in which case we need at least a link to them.

To say that another way, it's impossible to give CT or AC coast itinerary without knowing the destinations on either side of them. It's significant that the CT has a a shorter "season" than the AC. If you are going to AC first, you should not fly into Milan. I just bought some tickets (not to Italy) and they were among the cheapest air tickets to Europe I've bought in ten years. Milan can't be your only choice.

Thanks everyone for the input. Here are more specifics...

After days in AC or Cinque Terre we do Tuscany, Rome and then Venice.

We are going as a family of 5 in early October and we will be there for a little over 16 days.
We thought a hill town or two would be interesting for them and we were hoping for some pool/beach time for the girls to relax with no sight seeing. We love the Cinque Terre, but don't think we can do that and the Almafi coast in this trip. We thought the weather might be better in Almafi than the north. While we didn't make it to Como in our first trip, we thought given the weather might be cool that time of year, so that probably won't make it for this trip either, unless people think it's not to be missed.
We are flying in/out of Milan. Debating if we should go immediately to the south via plane or train and then work our way back up or the reverse.
The debate about train/car is really about costs and pool time -- we thought purchasing 5 train tickets may be expensive and a car might be more economical. Plus in Tuscany/Umbria and Almafi we thought we would stay outside of town so the kids could have some pool time again, so we figured we needed a car to get to the hotels or AirBnB's that have pools.

Given the amount of time you have and your other destinations, definitely suggest CT.

The AC is just too far away to efficiently work into to your schedule.

CT is,the better, more relaxing choice.

I would go to the Cinque Terre from Milan after landing.

If you arrive at MXP (you don't specify which Milan airport) the only flights to NAP are with Easyjet, and they depart in the morning, so you may not make it on time. Therefore to reach the AC, you are forced to use trains: MXP to Milano Centrale to Salerno, then ferry or bus, potentially a 9-10 hour trip. Therefore it will take the rest of the day from the moment you land to your arrival to the AC in the late evening at best, and if your flight is late, you may not even make it at all on the same day. That's a long journey for just a couple of nights.

The Cinque Terre are still a few hours away by train, but at least you have a chance to make it by early afternoon.

Lake Como is not on your list but is a bit closer by train from Milano than CT. This could be very relaxing before starting a big tour, and places you closer to Venice than CT.

Thank everyone for helping my wife and I plan our trip with our 3 daughters. This is how our itinerary is shaping out:

Oct 4- Fly into to Milan
Train to Cinque Terre -3 nights
Drive to Tuscany - 3 nights ( day trips to Pisa,Lucca San G. and Volterra
Orvieto - 1 night
RETURN RENTAL CAR
Train to Rome
Rome - 3 nights
Maybe Cortona for 1 day
Venice - 3 nights
Head to Mian for 1 night and head home!
Any suggestion or nights we should cut out or add would be helpful. Laura thanks for your suggestions about going to CT instead of the AC just a bit too far. I love CT just have to plan another trip. Let me know your thoughts. Thanks again everyone.

Oct 4- Fly into to Milan
Train to Cinque Terre -3 nights
Drive to Tuscany - 3 nights ( day trips to Pisa,Lucca San G. and Volterra
Orvieto - 1 night
RETURN RENTAL CAR
Train to Rome
Rome - 3 nights
Maybe Cortona for 1 day
Venice - 3 nights
Head to Mian for 1 night and head home!

To increase the relaxation factor in Tuscany, I would add the nights from Orvieto and Cortona to the 3 nights already planned in what I presume ot be the Tuscan countryside and settle yourselves into a nice agriturismo. Having a 5-night centerpiece to your trip will offer a respite from a relatively fast pace of travel and a chance to absorb. Maybe even take one day and have no car time, no day trips. Many agriturismi have animals, wineries, cooking classes, etc., that might be of interest. Besides, one night stays stink. You have to have one the night before you fly home as that is unavoidable.

I agree with the 5-day stay in Tuscany. We did that on our first trip (14 days) in 2010 and plan the same thing for our upcoming trip in September. We stayed in San Casciano in Val di pesa and plan to do so again, but I'm not sure it would suit your needs. However there are places a little farther south that give you more timely access to some of the towns that are a little out of reach for a leisurely day trip from SC. I seem to remember some of the places we looked at during our planning even had a pool. Good luck and enjoy the planning process....it can be almost as much fun as the trip itself!

I'll second Laurels' suggestion of 5 nites in Tuscany.

Think about this path, it would alternate relaxing areas with the cities.

Milan>CT.
CT>Rome.
Rome>Tuscany.
Tuscany>Venice.

You could train to Orvieto from Rome and pick up your car for Tuscany. From Tuscany, you could day trip to Cortona on your way to Venice and drop the car in Venice.