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8 night Northern Italy Holiday

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Hello,

My boyfriend and I are traveling from NYC to Milan in three weeks (we have 8 nights total in Italy). Our current plan is to grab the rental car and head to Lake Garda for 2 nights, then Venice for 2 nights, then drive down to Cortona for 3 nights. Due to our early Flight back from Milan, we were thinking of staying our last eve in Milan (wish to avoid the 4 hr drive back the morning of our departure). That mentioned: I assume there's a better idea for an itinerary.

Perhaps we should first drive to the Tuscany area (do you recommend Cortona), then Venice and wrap up in Lake Garda. We can stay in three hotels vs four as we'd plan to drive back in the am of our flight vs stay in Milan the eve before. Is Lake Garda too aggressive of a drive for a 1pm flight (drop the car off about 9:45am). Any thoughts on this?

Also, I used airbnb.com and had a great experience in the US. Though we have hotels scheduled in Italy; I wonder if I should scrap that and save a lot of money (perhaps) on using a hosts place via the airbnb.com service. Any thoughts/guidance?
Many thanks!
Cheers,
Paula

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