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18 Days in Italy! Input to finalize itinerary, book apts/hotels please!

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24 years after first dreaming of visiting Italy, my husband and I have booked our flights for an 18 day visit to Italy in May 2014! We have the "bones" of our itinerary but would welcome input about day trips, the order in which to connect Florence, Assisi, Orvieto, and Rome, and towns we might add in or leave out. We like to "pack in" as many experiences as we can without becoming completely exhausted. (While we hope to return to Italy, there are so many other places we want to see that it may not happen at our ages - mid 60's). We view trips as primarily "educational" - learning about places and cultures and then experiencing them in person. We enjoy wandering around small towns but also enjoy the beauty of museums and churches, and visiting archaeological sites. (I would be happy to visit every possible church but my husband's tolerance for that is more limited, so we will concentrate on the "most recommended.") We don't shop, and while we look forward to enjoying a few good meals, we would rather grab a pizza or sandwich and see more sights than spend time eating lengthy lunches. We also enjoy natural beauty (our most recent trip was to Switzerland), and chose to go in May in hope of seeing Spring flowers as we pass through the countryside. I love to photograph what I see, so that tends to slow me down a bit.

We plan primarily to use public transportation but have looked at the possibility of renting a car for portions of the trip, although we would rather not unless it makes visiting certain places significantly easier.

We are looking for apartments in Varenna or Bellagio, Venice, Florence, and Rome but would also welcome suggestions on B&B's and hotels. Our preference is to keep lodging costs under an average of $150/night although we know that may be difficult in some places.

So here we go! I've been reading guide books, forums, and other sites, and here is what we have come up with so far -

Day 1 - Depart US
Day 2 - Arrive Milan at 11:50 am; train to Varenna; on to Bellagio if we stay there.
Day 3 - Relaxing on Lake Como (mid-lake ferry - Varenna/Bellagio/Menaggio)
Day 4 - More relaxing on Lake Como (mid-lake Ferry - Varenna/Bellagio/Menaggio)
Does the "slow boat" to/from Como pass by anything special we would miss by concentrating on the mid-lake ferry?
Note: I explored the possibility of the bus/train to St Moritz as we missed taking the Bernina Express when we visited Switzerland, but it sounds like this would make for a very long day trip. Comments from anyone who has done this?
Day 5 - Varenna or Bellagio to Verona and/or Padua; spend the night
Day 6 - Padua to Venice
Day 7 - Venice
Day 8 - Venice (Murano/Burano)
Day 9 - Venice to Florence; half day in Florence
Day 10-11-12-13 - visit Florence and day trips from Florence
Lucca/Pisa
Siena
Cinque Terre (I know it's a long day trip but would love to at least get a
glance at the towns, mostly by ferry if weather allows; may do one easy,
short hike
Would love to see Byzantine mosaics in Ravenna but it's a really long and
expensive round trip; have considered going on the way from Venice to
Florence but would arrive late in Florence, which we prefer not to do.
Comments from anyone who has done either of these options?
Day 14 - Florence to Assisi; stay overnight here, or go on to Orvieto
Day 15 - Orvieto; on to Rome
I have read various ways of connecting Florence-Siena-Assisi-Orvieto. Comments on the most practical way to do this?
Day 16- 17-18-19 - visit Rome
My husband is interested in a day trip to Pompeii but it is long and expensive; I think I would prefer Ostia Antica (I have been to Athens and loved visiting the ancient sites there.) Other suggestions for side trips from Rome? Note that we hope to "do" south of Rome on another trip.
Day 20 - flight departs 11:50 am

The "must-do's on the trip are Lake Como (to relax and overcome jet lag), Venice, Florence, Lucca, Pisa, Rome. The Cinque Terre looks amazing (my husband loves seaside towns), and Siena, Assisi, and Orvieto have been recommended by friends as well as by guidebooks and forums. Padua and Verona sound interesting but I wonder if we should head straight from Lake Como to Venice (the #1 destination of the trip) and use that day elsewhere. As I mentioned, I would love to see the Byzantine mosaics in Ravenna, but it just seems too time-consuming to get to. (Perhaps we'll get to stop on a cruise one day, or will visit Istanbul!) Suggestions on which of these "undecideds" you favor, why, and how to work them in would be appreciated. I know each person's preferences are personal to that individual, but reading the comments does give me new ideas to consider.

I hope to get the itinerary finalized so that I can begin booking accommodations very soon. Suggestions on the itinerary, how best to get from one place to another (I have researched connections on the trenitalia website and know to take the bus from Florence to Siena but there may be connections I haven't considered), places to stay, and places to eat on a budget (under $25 per person for dinner except for an occasional splurge; we are light eaters and don't drink) are welcomed!

Many thanks in advance!

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