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preliminary tour of ITALY itinerary [14 days]

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i am planning a 2 week trip to italy in september 2010, flying into rome and flying out of milan. this will be my first time visiting italy so i want to see as much as i can but still enjoy and experience each place as thoroughly as i can. my boyfriend and i are in our late 20s, major foodies and wine aficianados, very active, interested in a balanced trip of sightseeing/history and relaxation [coastal town/beach], i haven't purchased a guidebook yet, but know some of the cities that we would like to see: rome, amalfi coast/capri, tuscany [small towns and vineyards], florence, venice, and lake como. please let me know if this itinerary is feasible:

Sep 13 - JFK to rome
Sep 14 - day 1 - 8 AM arrival / try to have a relaxing / easy day in rome
Sep 15 - day 2 - rome
Sep 16 - day 3 - rome
Sep 17 - day 4 - rome
Sep 18 - day 5 - amalfi coast - positano/ravello
Sep 19 - day 6 - amalfi coast - positano/ravello
Sep 20 - day 7 - day trip to capri
Sep 21 - day 8 - amalfi coast - positano/ravello
Sep 22 - day 9 - tuscany - chianti / montepulciano / san gimignano
Sep 23 - day 10 - tuscany - chianti / montepulciano / san gimignano
Sep 24 - day 11 - tuscany - chianti / montepulciano / san gimignano
Sep 25 - day 12 - venice
Sep 26 - day 13 - venice
Sep 27 - day 14 - venice / train to milan, spend the night
Sep 28 - day 15 - fly out of milan - 10 AM

here are my biggest questions:
1. am I making a mistake by leaving out florence from our itinerary? or should I do at least a day while I am in tuscany?
2. which town in tuscany would be a good base to see the area? is a car necessary?
3. are there any other towns/areas that are more of a "must see" than the ones i listed as a first-timer in italy?

Any thoughts and/or suggestions would be appreciated! i haven't booked any hotels or train tickets yet so i am open to any and all ideas! :)

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