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First time to Europe (Italy) Itinerary and general planning questions

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Hi Everyone,
I am planning my frist trip to Europe in late spring of 2012 and have decided on two weeks in Italy.
Some of you have been following and helping me on my "to tour or not to tour" topic. Well I am pretty sure we (my husband and I) are not going to tour so I have decided to start a new thread to fine tune my intinerary and help me push forward on the actual planning and booking of my trip.
For those of you who have not been following here is a little back ground. My husband and I are in our mid and late 20s. We are both from small towns (especially him) and I have done much more long distance travel than he has, which still isn't saying much. Most of mine has been in the US with the exception of Mexico (which doesn't really count, you didn't even need a passport back then). So as far as Europe goes we are beginners! I have been cramming when it comes to research, using Fodors like it is my new best friend, my trusty Rick Steves guidebook (an out-dated version, but the 2012 copy is on pre-order for October) and various other websites.
At this point nothing is booked yet, which is where I am at. I am thinking the first thing to book would be airling tickets to nail down dates and rates then go on to hotels and eventually train tickets and activites.
Being a newbie I of course have some worries: like pickpocketing (as I have mentioned), getting lost (especially in the train stations...parlo solo un po' d' Italiano), and money. As far as the money things goes most people have been saying to take debit and credit and take cash out as we go (to take advantage of cash discounts etc) which is fine, but then I hear of machines that suck your cards in and credit exchange fees... please enlighten me on this if you can!

I am looking at May 13th- the 27th. Or April 22- May 6th. I am thinking a Sunday through a Sunday would be best. A lot of places seem to be closed Sundays from what I can see and those travel days are pretty much used up by the time you get there.

This is my current itinerary. A lot have said it seems too fast pace or that I am cheating Rome out of one more day. I would like to go with the idea that I will be back someday but I also don't want to miss a must have while I am there this time.

Day 1: Leave Seattle fly to Venice
Sleep in: Venice
Day 2,3, and 4: Venice...explore on foot and by Vaporetto, St Marks Square, Murano/Burano (possibly)
Sleep in: Venice
***I have three full days in Venice here, I concidered moving one of the days somewhere else but I know that first day we will be the most tired so I don't want to rush.***
Day 5: Travel to Cinque Terre (it is a 6 hour train trip, doesn't look like a night train is an option)
Sleep in: Cinque Terre (not sure which town yet)
Day 6 and 7: Cinque Terre... explore, hike, beach time, possibly kayak
Day 8: Travel to Florence (about 2.5 hours train travel)
Sleep in: Florence
***Could possibly Travel to Pisa from 5 Terre, see what we would like to see there and then travel on to Florence. They have a bag check at the Pisa train station. Are these safe?***
Day 9: Florence...Accadamia, Uffizi Gallery, general exploring and gelato of course
Sleep in: Florence
Day 10: Day trip to Pisa (if we do not go there on our way to Florence) for the Field of Miricles. Possibly explore more of Tuscany this day.
Sleep in: Florence
***I also have an option to stay in Siena with a day trip to Florence instead of staying there. Hotels in Siena seem to be cheaper. Again we could stop in Pisa on the way to Siena. Once again I am wondering about the security of the train station baggage check.***
Day 11: Travel to Rome (2.5 hours)
Sleep in Rome
Day 12 and 13: Rome...explore on foot and by bus, the Colloseum , The Vatican Museum including the Sistine Chapel and more
Day 14: Leave from Rome. Fly to Seattle

That's it. I still have a lot of research and fine tuning to do. You all have been so helpful. Any general frist time Europe tips are welcome! Thanks a bunch.

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