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Trip to Italy - please weigh in with suggestions and tips!!

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Greetings fellow travelers!

I am taking a trip to Italy with a friend later this month. We could really use any/all help with suggestions and advice in filling in our itinerary.
We know where we want to go, but need help with ideas of where to stay, what to see and what to do!
Our idea of perfect places to stay would be wineries that accommodate overnight guests, traditional, Italian places where we can get a real feel for the food, people, art and culture of Italy..
Here is our "penciled" itinerary -- please feel free to weigh in!
Many thanks in advance!!

Arrive ROME Wednesday, March 26

DEPART Friday 3/28 - GOAL is to spend time in TUSCANY countryside and FLORENCE for total of 4 days.
Can you help plan? Do we drive thru OVIETO and SIENNA on way? Thoughts regarding CINQUE TERRA?
Stay in FLORENCE and TUSCANY through 4/2 (Wineries to stay?)

Drive to MILAN 4/2 (Wednesday) thru 4/3

Drive to VERONA Friday 4/4 Tour Gorga Winery with owner/friend (Staying at Casino di Caccia winre resort)
Stay VERONA / BANDOLINA / LAKE GARDA area for VinItaly Expo on Sunday/Monday (4/6-4/7) Visit Romeo/Juliet castle, etc.

Drive to VENICE 4/8 (Tuesday)

Depart VENICE 4/10 (Thursday)
Begin to head back towards ROME to explore before flying back to USA on Monday 4/14

Unfortunately, I'm thinking we need to omit the Amalfi coast and Naples on this trip.
We will need to fill in between Venice and Rome. We will have 1 day.
Umbria? Advice?

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