My husband and I are planning to travel Italy in May 2020 for our 15 year anniversary. I am hoping to travel early May and for 12-14 days total. I would like to fly into Venice, stay 3 nights, train to Florence, stay 4-5 nights-maybe rent a car and explore the country side for a day. Then train to the Cinque Terra for two nights. From there I am not certain if we should fly out of the nearest airport, Pisa-where there are no direct flights home or travel to another city-spend one night there and try for a direct flight? I have visited Rome before ( which I would do again) but not Milan. Looking for advice and the less stress for us the better!
For a trip ending in CT, I would prefer leaving from Pisa ( assuming a decent flight time/routing) and not have to spend the extra time to get to Milan or Rome the day before to get a flight home.
My $0.02
The additional time/expense for a connection out of Pisa on the travel home day will be much less than going back to a major airport the day before the travel home day.
My answer depends on which airport you are flying to in the US, as well as the cost and difficulty of the various options. There's no simple one-size-fits-all answer.
Remember that for some flight options, you'll need to get to the airport vicinity the night before in order to make the flight with less stress.
So, which airport(s) are you looking to get back to? Play around with Kayak or Google Flights to see what the flights cost from various Italian airports, then figure what else is involved (such as airport hotel the night before).
Thank you for the feedback! We are flying back to Chicago International. Now from your feedback, I think we spend time in CT then travel back to Pisa for a night (Pisa wasn't totally on my must see list, but it seems less stressful) and fly out that airport. Kayak has a trip with one stop-13 hr. total going back to ORD. Doesn't look too expensive considering it's a multi-city $1178.00