How I did it: Here's a Lists of Bests list that shows the cities that we visited.
I used this site called Tripology to find a travel agent that I liked. In the end, I went with Nancy Whelchel who turned out to do a great job of figuring out the kind of trip I wanted, and then executing on the plan in a very organized manner.
This was the first time I used a travel agent and it actually worked out a lot better than I had hoped. A few days before the trip I received a packet in the mail with a full itinerary of our trip, according to the schedule and desires I had given. I had vouchers for people to pick us up at the airport, hotels, trains between cities, and other things like private cooking classes and wine tours. I referred to the itinerary as our "choose your own adventure" and consulted it whenever we needed something to do or were arriving in a new city.
I was a little afraid that having it all planned out would ruin some of the serendipity of the trip, but it did just the opposite. It provided a solid backbone upon which all the serendipity could live within. Instead of worrying about where we would stay or how we would get there, we got to focus on the food, the walks, the friends, and the gelato. Read how I did it… 5 years ago