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9 days in the lake region - please help with itinerary!

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Our annual European trip is fast approaching and in less than a month we will be off to Milan! From there we will proceed to Mennagio where we have already rented a flat for 5 days. We are a couple in mid/late 30's who enjoy traveling, sightseeing, good food and are in need of some R&R (2 kids, 2 jobs, need I say more?)...
I am hoping to get some feedback on the itinerary I have planned which is just a very rouhg draft so far, due to the lack of time to do proper research...
Here is what I have so far:
Day 1: arrive to Milan from NYC (flight lands at 8:30 am), rent a car at the airport ( already booked) and proceed to Mennagio. Q: Are there any nice place to stop over on the way, to explore and have lunch?
Eve1: explore Mennagio, dinner in Mennagio
Day 2: explore Lake Como. Originally, our plan was to do it by ferry but our flat owner offered us a boat rental. He says we don't need any special permit but I am still hesitant... Has any one done it? Also, looking for recommendations on which villas not to miss and where to have lunch/dinner...
Day 3: day trip to Lugano
Day 4: day trip on Bernina Express
Day 5: explore lake Maggiore and/or lake Orta
Day 6: relax on lake Como, visit some more villas, etc
Day 7: leave for Milan, looking for suggestions to stop over on the way to Milan as we don't need to be there until late afternoon/early evening
Day 8/Day 9: explore Milan
Day 10: leave for NY in the morning.

I am looking for feedback on this plan and suggestions for sights not to miss, as well as restaurants recommendations (we'd like to have a couple of special meals in Michellin star restaurants or similar, but mostly we are looking for places that use fresh local ingredients, and offer traditional menu as well as modern... Not in the same place, of course).
I will be very grateful for any recommendations as we have very limited time to research.
Thank you!

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