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Help with Itinerary (specific ?s around Emilia-Romagna, Tuscany, Naples)

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I've been reading through the numerous posts on itineraries, consulting our guidebooks, and perusing the internet in an effort to solidify our itinerary for a two-week trip next April. This could change as we continue learning about the destinations, but I'm looking for some initial thoughts on specific parts. And yes, this is a busy itinerary, but we're comfortable moving around frequently and with the amount of time we've spending in places (except where I have questions). We also are planning to go back to Italy in the future and see the west coast (Pisa, Cinque Terre, up to Milan), so we're thinking we'll have more time in Tuscany in the future

Day 1 (Saturday): Fly into Venice - arrive about noon
Day 2: Venice
Day 3: Venice
Day 4: Venice; evening train to Bologna / Modena
Day 5: Modena / Bologna
Day 6: E-R Food Tour; evening train to Florence
Day 7: Florence
Day 8: Florence
Day 9: Florence (1/2 day wine tour one of the days we're there)
Day 10: Early morning train to Naples (or late train to Naples and more time in Florence?)
Day 11: Pompeii; evening train to Rome
Day 12: Rome
Day 13: Rome
Day 14: Rome
Day 15: Rome
Day 16: Rome & fly home

Question 1: We know we want to do a food tour in Emilia-Romagna. Not sure on if we'd prefer Bologna or Modena. I've read good things about both; sounds like Modena is smaller but has beautiful sites. Any thoughts?

Question 2: Would Siena make a good day trip from Florence? Would the time be better spent with 2.5 days in Florence or take one out for Siena? (Pisa & Lucca we're saving for the next trip.)

Question 3: Still debating on spending most of a full day in Naples. if you've been, did you enjoy it? Or feel the time is better spent with extra time in Florence?

I'm sure I'll come up with more questions as time goes on. Thank you in advance!

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