Big essay first, a few questions later.
My husband and I have travelled a fair amount, both separately and together. We've gone on some smaller trips with our now 15-month old baby (including flying at Christmas as well as a couple of long car trips) and we think we're ready to take him to Italy. (I know that travelling with a two-year old sounds awful to some people, but we enjoy spending time with him. We understand that he might have bad days and are willing to take it easy in order to have him with us.) We're currently thinking we'll go in March of next year, to get the warmest weather possible while avoiding the crowds that come with Carnevale and Easter (and anything after Easter).
A little about us: We enjoy hiking, good food (but generally love "home-style" cooking rather than molecular gastronomy, tiny portions, or waitstaff who put our napkins in our laps for us), interesting architecture, and nature. Examples of places we really enjoyed were Santorini, Newgrange, the Alhambra, Montserrat, Eilan Donan castle, and pretty much everything else about the Isle of Skye. I've been to Italy twice (Rome, Florence, Cinque Terre, Venice, short stops in Lucca, Pisa, Assisi, and Verona); my husband has never been.
Where it's available, we like to take the train rather than bus or renting a car. In the past, I have generally pre-booked a lot of things, and we have been willing to handle long days of travel or long day trips, but we expect that having our then 2-year old along will change our travel style. In planning this trip, I've tried to aim for about two hours of transit per day with a maximum of four hours per day (well, other than our flights to and from Italy - we live in Seattle). We'll pre-book hotels and a few things (an early morning entrance into the Vatican Museums, for example), but otherwise, I'm going to try to play it by ear a little more than I normally do. We generally try not to spend just one night anywhere, and I think that's especially important because we'll have our son with us.
Lodging-wise, we're hoping to have a crib as well as a separate room for our little guy in most cities to help us all sleep better. We know that won't be cheap (and are looking at apartment rentals - some seem to have cribs available), but we're still hoping to spend less than $300 a night on lodging.
Our current itinerary is:
Fly into Rome
Rome for 5 nights
Sorrento for 3 nights, including a day trip to Pompeii
Orvieto for 2 nights, including a day trip to Civita
Assisi for 2 nights
Florence for 3 nights
Venice for 4 nights
Leave from Venice
First question: We have two more nights. Where would you spend them? I loved Cinque Terre, particularly the hikes between the cities, and I really want to shove it into this trip, but I'm concerned that we would need to give the CT three or four days - I did the hike in a day when I was there, but I can't imagine my son would have the patience to hang out in his carrier that long (or the focused energy to do the hike). I did not particularly like Florence either time that we were there. To be honest, it's in this itinerary more as a convenient stopping place between Assisi and Venice than anything else, so I probably would not add time there - I keep trying to shave time off from Florence and add in the CT, but my logical side says that's a bad idea and I should add more time to existing cities instead.
Second question: I'm concerned that the Amalfi Coast bus won't really work out with my son - I've read it's three hours - and the ferry doesn't seem to run until the summer. Does the bus to Positano and back to Sorrento sound like a good idea? I might consider using the extra days above for that.
Third question, more general: Any other recommendations for us, especially with respect to lodging?
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Big essay first, a few questions later.