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Itinerary help for tight Tuscany-Bologna trip

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This is my first draft of an itinerary, so I'm eager to get some Fodor's input! I realize this seems like a lot of places in a short time, but we are working around our adult children’s short vacations from work. Our main interests are food & scenery (vs museums). Our key places to see are: Rome, Chianti/Tuscany, Bologna, Venice & Florence. Whew. I realize that we aren’t giving Florence or Bologna the time they deserve, but we don’t know if we’ll be back, so is some time better than none?

We are a group of 6, and only one has not been to Italy before - so this itinerary is trying to please many wish lists!

Day 1: ROME: Arrive early morning: check-in hotel, see Sistine Chapel (can this be done without a Vatican tour?), Trevi Foundain, Spanish Steps

Day 2: ROME: Colosseum, Appian Way bike tour

Day 3: ROME to CHIANTI: Train from Rome to Chiusi in morning. Get rental car and drive to Montepulciano for lunch, explore then drive to somewhere in Chianti for 3-4 nights. We'd like to be able to walk to restaurants, vs far out of a town. So any accommodation recommendations are very welcome!

Day 4: CHIANTI: Explore towns, eg Castellina in Chianti, Certaldo, Colle di Val d’Elsa, Montevarchi, Greve in Chianti, Panzano, Volpaia, Lamone (not all of these in one day of course!! Just ideas picked up from the forum…I’ve already been to Volterra, San Gimi, Orvieto – others in group been to Siena)

Day 5: CHIANTI: More exploration of small towns.

DAY 6: FLORENCE or BOLOGNA: This day is flexible, but for now:
Drive to Florence, return rental car. Florence in one day sounds challenging but I don’t know when or if we’ll make it back to Italy, so I’d like to at least see either/both Galleria degli Uffizi or Galleria dell'Accademia.
- Spend the night in Florence or train to Bologna. ???????? Help!

DAY 7: FLORENCE/BOLOGNA - VENICE:
- Have lunch in Bologna (not sure if we have time for any food tours, and whether all 6 of us want to do that. But we’ll eat for sure!!) Recommendations?
- Train to Venice in late afternoon

DAY 8: VENICE (Most of us have been before)
DAY 9: Flight home

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