Stuck in the 7th Level of Dante's Itinerary Purgatory! Please Help!

Elle, Actually, your proposed Itinerary seems to be reasonably well paced, with adequate time in each location (including Sorrento) AND most importantly adequate travel times. What are your concerns about the Amalfi Coast portion? Arriving in Florence on a Sunday should be fine. Just plan to do a bit of exploring in the city, rather than visiting Museums or whatever. You can do that on Monday. Of course, reservations for the Accademia and Uffizi would be advisable (if you were planning to visit there). Happy travels!

It will be difficult to visit the Florence museums on Mondays. That's when they're closed. Also, when train strikes happen, they tend to be on Sundays, so I try to avoid those as travel days. Just to give you more to think about. :-) I would drop a day from the CT and from Sorrento and put them on Venice and Florence, but maybe that's just me. Also, Assisi to Sorrento is going to be an ugly travel day. It takes at least four hours just to get to Naples from Assisi. How about dropping Sorrento entirely, and spend more time at all your other places? Maybe throw in Orvieto for a couple of nights?

I was thinking of spending a couple days in a hilltop town (Volterra or San Gimignano) after Siena and then going down to Assisi to coincide with the Feast of Saint Francis on October 4. I could head to Orvieto/Civita di Bagnoregio for a couple of days before heading to Rome. As my itinerary stands, I would be in Assisi 2 days before the Feast of Saint Francis followed by, as Michael pointed out, a nightmare of a train ride to Sorrento. That wasted time on the train does bother me--I'm used to trains (New York) but 6 hours seems excessive...

Elle, "I'm used to trains (New York) but 6 hours seems excessive" Actually, six hours isn't too bad. I've found that's often necessary when moving around Europe. If a rail trip is >8 hours (or so), I'll consider using a budget airline (although I try to avoid the usual "airport hassles" whenever possible).

I spent a week in Assisi last year, including the feast of St Francis. I was expecting a zoo, but it was a wonderful experience (both the procession/celebration in the town, and the level of attentiveness/reverence during Mass). I'd recommend getting there a day or so before the celebration; it would be really difficult to arrive that day and find your way to lodging.

Elle
Your trip is certainly doable, though I would be tempted to leave Amalfi for another trip. Florence on a Monday might be somewhat disappointing as most of the major sites are closed. Just a thought but you could add a couple of days to Venice and maybe do day trips to Padova and or Ravenna. Go on to Riomaggiore. Then on to Assisi. From Assisi go back to Florence for three days- do Siena as a long daytrip using the Sita bus. See the sights, stroll the Campo have a fabulous dinner take a late bus back to Florence. Add a day to Rome and use it for a day trip to Orvieto by train- or take the train from Florence to Orvieto and spend a night there then take the train into Rome.

Unless you are hiking it seems to me that 2 full days in Riomaggiore might be too many, while a half to one day in Siena may not be enough. Also, you have too much time in Sorrento for me, unless you are going over to the Amalfi coast. It isn't cheap getting from Sorrento over to Amalfi so you might want to stay on the coast.

Elle, your plan seems ok except for Cinque Terre. I would suggest you do it between Venice and Florence. this way you can also stop for a few hours in Pisa ( if you did not see it) This way also your days in Florence will not be on a Monday.
Last summer we spent enough time in Florence and in Rome to buy the pass for museum (Roma pass and Firenze card) and in Venice to buy the vaporetto 48 h pass (or was it 72h?) as we extensively used them Have a nice trip

I think it is a nicely balanced trip. I might suggest combining Florence and Siena (stay in Siena 4 nights, daytrip to Florence). 3 nights on the CT is nice: hike 1/2 day each day, kick around the towns the rest of the days. R.S. has self-guided tours for each and they are quite nice walks. Plus the food is GREAT and worth staying three nights to eat in the CT. We spent a week in Sorrento and never ran out of things to do. A day for Pompeii and Ercolano, a day for the AC (not expensive; take the bus and buy a day ticket for a round trip; it was 7.40 euros for a 24 hour ticket last Dec.), a day for Naples if you like, or Capri, or just hang out in Sorrento. Yes it's a long travel day to Sorrento from Assisi, but I like those a couple of times in a long trip. Nice to just enjoy the trains sometimes. Venice to the CT or the CT to Siena are kind of long days too. Depends on the final routing you decide on.

I like your trip as it currently is set up. In considering whether to do the Cinque Terre in between Venice & Florence, for me the train schedules would be the determining factor. When going from Venice to Riomaggiore, it is a long train ride because of the transfer times and number of train changes. However, to go from Riomaggiore to Siena, you will most likely have to go back to Florence. So, it may be a toss up. From Florence to Siena, RS suggests taking the bus rather than the train. This could also be a long travel day. Have a great trip!

Elle, With the train going direct from Venezia to Firenze, I'd do those one after the other, and then hit the CT. If you like hiking at all, then the CT is fantastic. After the CT, I found the Amalfi coast quite a bit less interesting, so I wonder about the amount of time you have for Sorrento, although as someone else said, if you go to Capri, do the AC, and do Pompei (a must, in my opinion), then you've used up your time in Sorrento. Assisi is great. Siena less so. We enjoyed going to the Tuscan towns of Volterra and San Gimignano more than Siena, so perhaps you can soak up your Siena time doing that. Enjoy the trip!

the suggestion to do Cinque Terre before Florence works very well if yo are driving. I would not know about the train however

Have a wonderful trip. As others have mentioned, you need to check on the museums in Florence. Most closed on Mondays, Accademia and Uffizi. We went to the Amalfi Coast during our trip in April 2012. IMHO I enjoyed the cities (Rome and Firenze) more. Maybe because I've had other vacations with beautiful natural sights. If you are definitely going as far as Sorrento then, I would suggest taking 1 day for a tour of the towns, Positano is lovely.

Have a wonderful trip. As others have mentioned, you need to check on the museums in Florence. Most closed on Mondays, Accademia and Uffizi. We went to the Amalfi Coast during our trip in April 2012. IMHO I enjoyed the cities (Rome and Firenze) more. Maybe because I've had other vacations with beautiful natural sights. If you are definitely going as far as Sorrento then, I would suggest taking 1 day for a tour of the towns, Positano is lovely.