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Traveling for First time to Italy and Spain. NEED HELP!!

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All you seasoned travelers out there, I desperately need your help! My 21 year old daughter and I are going to Italy and Spain from May 8-28. Schedule right now is arrive in Milan, spend one night, go to Venice for 3 nights, go to Florence 4 nights, go to Rome 3 nights, go to Naples 2 nights, fly to Barcelona 4 nights, go to Madrid 2 nights. Already booked hotel in Milan and apartment in Venice. Have apartment in Rome but we can switch those dates around as it is with a friend.

Should we be doing this another way to fly out of an easier, closer airport to Spain than Naples?

We are also having a very hard time booking lodging so I thought maybe changing dates around might help.

I am completely overwhelmed! Would also love info on getting around by rail and bus. Best companies, best way to do it and still keep on some kind of budget. Way too much info on internet. i am about to give up and cancel trip. HELP PLEASE!

THANKS ALL!!!

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