Italy
We took a 7 day Mediterranean cruise about 4 years ago that started in Barcelona, stopped a couple places in France (Villefranche, where we took a city bus on our own to Eze and another to Nice for one day) and then Livorno, Italy (bus to Florence for the day), Naples (we did an Amalfi coast tour by bus (can't imagine driving that one on own and live to tell about it- some people did the Isle of Capri tour which also got raves), then to Messina (industrial port in Sicily took a cab with another couple to Taormina - about an hour away - for the day - gorgeous, and ended in Civitavecchia (nearest port to Rome). Took a bus to Rome and stayed for another 3 days in a hotel and flew home from there. We were with a group from Ohio, but could have done this on our own as well. About half the time we did our own tour arranging, the rest thru the cruiseline.
There are longer cruises that end up in Venice. If you haven't done a lot of travel in Europe, this is a nice way to see quite a bit and have some time on your own at the end. I prefer it to a bus-type tour because you don't have to have your bags packed outside your door at 6 or 7 am every day.
If we weren't with a group, could have then taken a train or driven (I'm not as brave as the previous poster) to the hill country, lake country or wherever after seeing Rome.
I've been to Europe about 4 times now, and am a fairly adventurous traveler who normally does a lot of prepration (studying maps, reading travel books, etc). Now I might do ok on my own and I do agree that part of the fun is stumbling on delightful scenes and sidetrips, but if it's your first time to Italy and you don't speak Italian there's some comfort with some structure for most of us.
First time I went was about 10 years ago - my daughter met me and my sisters at the airport in Paris at the end of her semester in Luxembourg. We had planned our itinerary, had reservations in 3-4 cities in 4 countries and a 2-3 night Rhine river cruise in the middle of it all. I don't know that we would ever have found the train station, let along the hotel, if it weren't for her experienced help.
Just something to consider instead of a tour company by land - or maybe you could do a combination - cruise for the port cities and a tour on either end. Cruise prices seem really good this year.
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