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Please help/critic our Italy trip!

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We are going on a family trip of 8 (I know.. CRAZY).

Here is our plan. Tickets and Rome hotel are booked. Trying to figure out if our plans for transport/locations are feasible. We are flying into ROME on May 3rd, and flying out of Florence on May 11th.

Our planned itinerary is as follows:

Sat- May 3rd: Rome. Sleep Rome.
Sun- May 4th: Rome. Sleep Rome.
Mon- May 5th: Rome/Vatican. Sleep Rome.
Tues- May 6th: Rome. Sleep Pompeii.
Wed- May 7th: Pompeii. Sleep Chianti (Greve?)
Thurs- May 8th: Chianti Sleep Chianti
Fri- May 9th: Pisa Sleep Chianti
Sat- May 10th: Florence Sleep Florence
Sun- May 11th: Fly out in AM

We are planning on renting a car, since we heard you really need a car in Tuscany. So our idea was to rent a car our last day in Rome and drive to Pompeii, then drive up to Chianti area and do day trips from a base in Greve. Van for 8 at around $650 for this time period (rent in ROME return in FLORENCE).

What do you think? A few questions:
-Is it too ambitious to drive from Rome to Pompeii, then up to Chianti? I heard driving in Naples is a nightmare. Is it possible to avoid Naples completely when driving to Pompeii?
-Do we need more time in Pompeii? Should we sleep in Sorrento instead?

Any and every thought is appreciated! Thanks!

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