You're a travel moron if it takes you months to figure out how to plan a vacation in Italy. I could do it in an afternoon with the internet and any good travel guide tailored to the price range and experience I'm after.
Further, there are travel and lodging offices in ever medium to large train station in Europe. It's easy peasy. I once flew to Athen's Greece at the last minute to catch the last of the sunny beach weather.
I reserved a car service to pick me up at 5AM at the new Athen's airport, via email, asked for 2 1 liter bottles of water to be in the car for me. Booked 1 night in the cheapest decent hotel in Athens, and booked the car to take me back to the airport in the morning for a connection to Mykonos.
Got to Mykonos, walked out of the airport, and up to the first hotel shuttle I saw (it was hot out) and asked the average room rates for their hotel, agreed, said "let's do it," got on the shuttle. On the shuttle was a hot coed grad student and her blond hot stepmother.
I knew Mykonos well enough to get around without a map. The gal and her stepmom wanted me to show them around cos the stepmom was at the end of her vacation and had to leave in 2 days. Showed them around, help them but their Greek trinkets (classic Greek striped sailing sweathers. Stepmom flew out, stepdaughter, 28, traveled dance and canoodled with me for the next two weeks and then head out on her open ticket round the world trip.
You can plan a European vacation with no planning! If you are European -- or know the ropes. Every place essentially works the same, you just have to know what you are doing, and be smart and flexible and have the cash to spend extra if needed. (Once got into Bologna late and had to get a $300. @ night room. Which, I amortized by spending $15. a night in a good hostel in Florence for 5 days.
I alway use 3 travel books. Let's Go Europe, to get the latest on deals on the low end. Rick Steve's for the MILFs and PBS educated. And Frommers or DK for a little tonier.