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Please review my 9 day Italy Itinerary!

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Hello all,
Need your expert advice. I am traveling to italy with my husband, 2 boys (ages 5 and 2.5), my mom and brother in May:

May 4: depart NYC to Rome
May 5: land in Rome and take train straight to Florence
May 6: Florence sightseeing
May 7: Rent car - Day trip to Siena and San Gimignano (Banfi winery) - considering going to Pisa to see Leaning Tower but is it worth it?
May 8: Florence to Rome by train
May 9: Rome sightseeing
May 10: Rome sightseeing
May 11: Cooking Class/Vatican
May 12: Day trip - please advise (a winery, or a 'must see' town that's close by
May 13: Last day in Rome (shopping, etc.)
May 14: Fly back to NYC

I have the following questions.

Do you think we need to go to Pisa? I thought the kids would like to see the leaning tower

Cooking class - any recommendations for a kid friendly cooking class for pizza/pasta (vegetarian friendly)

Olive Oil farm - should we do this?

Open air concert/Opera- I thought I would book something like this for my and my mom - any recommendations?

Should we buy the ROMA pass?

We are in Florence for 4 days and then Rome for 5 days - do you think we should do a night in another city to break things up? Or are we being too ambitious to think that?

Any restaurant recommendations in Rome/Florence that is kid friendly and vegetarian friendly would be great!

THANK YOU!!! :)

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