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10-11 Nights in Italy with extended family - itinerary help, please.

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Thank you in advance for your help. I continuing to research on the forums, but I thought I might ask for some preliminary help on our itinerary.

In any case, this summer we are traveling to Italy (!) for 10-11 nights. At this point, the group includes my family of 3, my sister in law, and my in laws. My main concern right now is planning our itinerary and booking accommodations for the latter part of our trip considering we are going in high season.

The set plan is as follows:

Day 1: Fly into Milan. Stay in Milan overnight. This isn't my choice as I'd push on, but it's fairly set due to the needs of the other travelers.

Days 2-5: Lake Iseo to see the Christo exhibit. We have already booked lakeview rooms. I cannot shorten this part of the trip. I assume we will do day trips - Verona? - but I'll worry about that later.

Here's where I need help: We have 5 nights left. I'd like to go to a villa somewhere between Lake Iseo and Rome and spend some time relaxing in a beautiful location, let the child run around, hire a cook - maybe try and organize a tour of some vineyards. I'm not fussy about where as long as it makes geographical sense.

However, we'll be flying out of Rome and obviously, we need to go to Rome! Thinking of renting an apartment in the Prati area or finding an apartment-style hotel.

With just 5 days, it seems to make sense just to spend it in Rome since there is so much to do but part of me feels really sad to give up the idea of lounging in an Italian Villa.

Any input appreciated - thank you again!

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