If you want to add Cinque Terre on top of Amalfi, much less Venice, Florence, the Florentine countryside, and Rome, it is not doable. Italy is not Hawaii. You can drive from Waikiki to the furthest beach on Oahu in an hour and a half. You are talking about a whole country here.

I understand the points and the money aspect, but you are going to be reducing your vacation to just a series of drive-by stops to take a photo. If you don't focus down, when you get back you will have no more feel of Italy than if you watched National Geographic. I have a friend who told me she's, "been to Venice." She was on a cruise stopped there for a day. She might as well have visited the Venetian Hotel in Las Vegas.

OK, financial constraints have to be respected, so you have to leave Venice. As for Florence, if you consider Ponte Vecchio to be dead center of the historic center of Venice, each of those properties is about an hour walk away. That's not what you want to be doing at 11PM after a great meal and bottle of wine. Yes, you can always get a cab.

You originally mentioned four days in Florence, but I'm confused because now you say, "we may only spend 1-2 days and maybe an extra meal in the city its more of a home base." You will have little time in Venice, now only 1-2 days in Florence, it's not clear what you will be visiting. You have to choose an area, and stay with it for at least a few days.

Cinque Terre means five lands or towns. You can't see five towns on a day trip. If you stay at one of those towns you can explore two or three more, but staying in Florence as a base to explore Cinque Terre as a day trip is too much, while you also want to see, "the countryside of Florence." It's like throwing away a day. You will have no idea of what the Cinque Terre is about if you just buzz through it just to say you've "seen it." You can't eat the whole Thanksgiving Turkey without indigestion and a spoiled meal.

For Amalfi Coast, "that is the one place my wife wants to visit," I'd respect that. September is not a bad time to do that. It will still be crowded, but not at absolute peak. It's just before the rain starts. The weather is usually great. Given what it seems is attractive to you, I'd stay in Positano for the four nights your originally planned.

You are doing really well here, but you should be trimming, not adding. You said you have two weeks. Assuming a lost day at the end, you have 13 days. Take away 2 for Venice, 4 for Rome, and and four for Amalfi, how are you going to squeeze in Florence itself, the countryside of Florence, and the five cities of the Cinque Terre all in there in the three days that are left? That is assuming 3 days. At least 12-18 hours of those 3 days will be spent traveling.

The biggest mistake when traveling to Italy is trying to digest it all at once.

All of Florence is close to the airport. Proximity to the airport shouldn't factor into anything. If you are landing in Venice and departing from Naples, why would you have an interest in the Florentine airport?