I think you have two young kids with you? You aren't leaving much down time and some of these may be a bit much for your kids. You will be go go go all day, in transit a lot as well I would scale back and attempt about half of this...

The bus ride to and from Positano may be very crowded, you may need to stand, and the corners are very sharp...this may also be very difficult with young kids. The towns are quite vertical as well.

Attempting Pompeii and Herculaneum in one day with young kids I think may also be too much.

Just some things to think about...

I did exactly the same thing plus another day for Ischia, which I enjoyed as much as much more touristed Capri but I did not have kids in tow.

Sounds perfect except Pompei and Herculaneum is probably too much for one day - pick one. Pompei is easy to get to from Sorrento - take the little train (I forget what they call it)

Herculaneum and Pompeii are both on the Circumvesuviana train line that runs between Naples and Sorrento. Sorrento is the end of the line.

Ok great! I will take day trips only if my kids will be fine. They are generally OK - fingers crossed!

Flights booked from Milan to Naples!

Is there anything Must See in Naples?

>>>We will take a train from Naples and base our-self for 5 days in Sorrento.<<<

You should take the Curreri bus (10€)from the airport to Sorrento instead of the train. To catch the train, you would have to take a bus into Naples and then catch the train. The bus doesn't go into Naples. Click the timetable link on the right side where it says "bus connection - see timetables".
http://www.curreriviaggi.it/inglese/E_index.html

Thank you for the great suggestion!!!

What time of year are you going? Is it May/June with longer days (and sights open longer)?

And how old are the kids - these days sound awfully busy unless they are teens.

We are going in may end. My kids are 5 and 1.

I think your Capri day is crazy busy for young children. You should check into age restrictions for the Blue Grotto since you have to transfer to small rowboats to get into the grotto, cannot imagine the 1 year old in that situation.

I don't know if they will allow a one year old to go in the Blue Grotto. You have to transfer to a small row boat.

You might want to buy your ferry tickets when you arrive in Sorrento or you might not get the time you want the next morning.

In that case- we will skip Blue Grutto- no issues. Thanks!

OP>Does this all sound reasonable & doable on your own<

To be really honest, to me it does not seem like a reasonable trip with two little ones the age of yours.

Listen to Socaltraveler. Lifting a small child from one boat to another in the water is not something I would want to do. Here is how it works. You take one boat to the mouth of the Grotto. Then one by one you transfer 3/4 people from that boat by stepping across into a very tiny boat that then is rowed/pulled through the mouth of the cave. Sometimes you just about have to lay down to get through. Your kids are too small to step from one boat to another. You would have to pass them over. It isn't a sensible thing to do, and Socaltraveler is probably right that they may not even be allowed.

Day 3 with two little kids may be doable, but is not at all reasonable. The ferry where they could at least walk around might be more comfortable than the bus. Positano is mostly steep stairs. Your little one will not be able to walk the stairs and it won't be much fun carrying a child on your back while climbing them. Look at some really good pictures of Positano to see what I am talking about.

Pompeii is all stones - some fairly large, so not easy walking. It will be very hard for your really little kid.

If you were just going to some beautiful place with great views and a pool for the kids, the AC would be fine, but all these trips with the kids sounds difficult, IMHO. There are so many interesting places in Italy that would work better with children that small.

Are you still going to the Lakes area?

Sorry, didn't see that you had already ruled the grotto out.

No Problem - it happens!

Would suggest visiting Herculaneum rather than Pompeii - your 5-year old won't know the difference. Herculaneum doesn't have the cobblestones like Pompeii does, and if you're pushing a stroller, cobblestones won't be any fun. Herculaneum is also a much smaller site and shouldn't be as exhausting for your kids. You might also want to consider visiting the Amalfi coast when your kids are older. Why not slow the pace down and stay in Sorrento and enjoy some beach time with them? There's also a little white tourist train in Sorrento that goes around the city - your kids might like that.

You do not need to rule out the Blue Grotto. I agree that the one year old is probably too young, but the five year old might like it. And anyway you could go while the kids stay on the larger boat with your husband, then when you get back he goes. The bigger boat hangs out there for half an hour or more while the rowboats take numerous groups into the grotto, so no problem as long as you and your husband are ok with not going in the same row boat. My husband and I almost didn't go cause it looked so touristy, and the water all around Capri was so blue I couldn't image how being inside that little cave could be significantly better - but it was! I will never not do something again because it seems 'too touristy'.

We were in Sorrento 8 days and did all the things you mention (except Herculaneum) and really didn't feel too rushed. We did a number of fairly strenuous hikes you obviously can't do with kids that age, but if you are used to carrying around the one year old and the five year old is a good walker I think you will be fine. You may end up shortening a few days if the kids get tired, but I wouldn't rule things out.

Here's my trip report and link to photos - http://www.fodors.com/community/europe/amalfi-coast-rome-and-croatia-images-of-three-hot-but-wonderful-weeks.cfm

Thank you Isabel! This is motivating- my kids are generally fins and have vsiited a lot of places with us with no issues. We will play by year and do things that we all can handle with stress.

I meant "without stress" lol

Can we base ourself in Naples and still do these day trips easily? We are not able to find decent /reasonable lodging yet in Sorrento and hence checking about Naples as a backup.

Pompeii can be hellishly hot so make sure you have hats, SPF and water. If I go again, I'm taking a little umbrella to give some sun protection.

I stayed in a great place in Sorrento last month, beautiful, friendly and very reasonable. In a great location. Casa Astarita. http://www.casastarita.com I recommend it HIGHLY.

MmePerdu, Thanks. Looks so good, I'm bookmarking

Hi, what do you mean as 'decent/reasonable lodging'? Because Sorrento accommodation are amid the most stunning of Amalfi Coast! Have a look on this http://www.hoteldelfino.com/ which is right on the coast between Sorrento and Massa Lubrense, so very quiet. Phone the staff up and ask them to arrange transfer from Naples for you, they are very kind.

Our budget is $200/night! Hoteldelfino looks good but a little expensive to spent about 1200 for 4 nights! Any other suggestions? Is Naples OK to stay?

Have you looked at an apartment rental for the 4 nights - more space, and perhaps an opportunity to do laundry, too. Naples would be far, I think, with transporting your young children, to parts of the AC, maybe ok for Capril and Pompeii. Pompeii will be a very long and hot day for small children, bring lots of water.