My fiance and I will be in southern France for a friend's wedding, and would love to check out Italy since it's so close. I had a "master plan," that had us going from Nice-->Florence-->Greve (Chianti)-->Siena-->Sorrento/Amalfi Coast-->Rome (just for our return flight), BUT just noticed that it's both difficult and expensive to get to Florence (by train and/or flights). Surprisingly, it appears cheaper and easier to fly to Naples so considering doing our trip in reverse and possibly getting rid of own town/region.
We have already booked our return flight home out of Rome, so hoping to get recommendations that makes more sense logistically/geographically, as we do not want to move around every few days; rather, we'd ideally only stay in three to four places max throughout the 17 days to really take in each town and do day-trips to nearby attractions. My fiance is a competitive cyclist, so Tuscany and Umbria seem pretty perfect for him, while still having many amenities for me to entertain myself/go on casual bike rides when he goes out for a long ride. Lastly, I know that we're going during a busy season (June) so anticipate it being crowded, but welcome any recommendations on hill towns in Umbria/Tuscany that may be a liiiiitle less congested and a solid home base :) Assisi seems gorgeous, but is it too crowded? Orvieto..is there enough to do for a 5-6 days there?
Here is my original and revised itinerary. Thank you in advance!
Current Plan
(5 nights): Sorrento/Amalfi Coast (Fly from Nice-->Naples; bus/rental car from Naples-->Sorrento)
(5 nights): (TBD) small hill town in either Umbria or Tuscany
(4 nights): (TBD) small hill town in either Umbria or Tuscany..or should we just add a few days to each of the above?
(2 nights): Rome (1 hr bus to Naples--> 1 hr-speed train to Rome)
(last day) fly home
Original "Master Plan" (before I looked at transportation from Nice to Florence)
(2 nights): Florence
(5 nights): Greve (Chianti region)
(3 nights): Siena (1 hr drive from Greve)
(5 nights): Sorrento (5 hr drive/6 hour train from Siena-->Florence-->Naples-->Sorento)
(2 nights): Rome (1 hr bus to Naples--> 1 hr-speed train to Rome)
(last day) fly home