Late one evening at a friend's friend's house, I saw a picture from the Positano bus stop, and I had to go there. When the picture was brought up to those at the table, I learned I was the only one in attendance who had never been to Italy.
So, we went.
Using the internet, Rick Steves' Italy 2005 guide book and recommendations from friends, The Girlfriend and I planned the entire trip ourselves. When we tried to go through the travel agency Select Italy, we struggled to get them to even return phone calls, much less answer e-mails.
Our Italian friends (who go to Italy once a year) suggested late September or early October for our vacation, as the weather is just perfect where it's not too hot, but not to chilly. Plus, it is after the Italians have returned from their Summer holiday, so most places are open and running with full staff.
The mistake I made in planning my first big trip out of the country was picking the dates, then filling in the time between flights. Instead, I should have plotted everything out, then book the flights (in the end, this was not a problem because we decided to see Rome South, and nearly two weeks was perfect). The only thing I really struggled with when planning everything without a travel agency was were to go in Sicily. A friend had been there and said it was his favorite part of Italy, including the train ride on a barge to get from the mainland to the island. Luckily, I stumbled upon a Budget Travel Online's "Trip Coach" were Reid Bramblett answered my question of where to go with such limited time.
You know that scene at the end of Indiana Jones and the Last Crusade when the characters must choose the cup which Christ drank out of at the last supper? The one guy chose wrong and promptly gasped and aged super-fast until he died? While at the Vatican, visitors have the ability to drink holy water bubbling from a fountain. There was a brief moment before I gulped where the aforementioned scene quickly flashed through my head. Luckily I walked away unscathed, and a little on the blessed side.