Posted November 18th, 2017, 09:07 AM
Just a few thoughts for the OP.
One of my rare differences of opinion with Hank - I rate a trans-Atlantic repo cruise as a poor use of time. If you cruise for the ship & the sea, repo cruises are great value. But that's a lot of days at sea - days you could be exploring foreign lands.
I suggest a 10 to12 day one-way cruise.
Since your focus seems to be on Italy, mebbe Rome to Venice
or vice-versa. Several mainstream cruise lines offer this. It means you can spend pre-cruise time in Rome (I agree with Bruce that in your circumstances around 3 nights is good for Rome). Several Italian ports, Greek islands and a port or two on the Adriatic coast of Albania / Montenegro / Croatia - a good mix of ports, & a cruise ship is by far the easiest & most economical (money and time) way to visit most of those places.
Or perhaps you want to major on Italy for the land portion of your vacation? So perhaps Barcelona to Rome via a French port or two, then explore Italy by road or rail.
You need to decide whether you want to major on cities or countryside.
The depth of your wallet comes into it too
Those things will to some extent dictate your transportation - plane or train or car.
If you want to major on cities your best bet will be trains and/or planes. The rail system in Europe is excellent, and there are various ticketing options which significantly reduce the cost of frequent use. A car is a hindrance rather than an asset in a great many European cities, same as in a comparatively few US cities like NYC and Chicago. If you choose to travel by car, for most cities it's simpler & cheaper to lodge somewhere out-of-town with ample parking and good transport links into the city. If you choose a hotel in a city centre, make sure you can book parking with it - though parking might cost almost as much as a room.
By plane, most cities in Europe are within an hour or two of each-other, so even allowing time for travel to/from airport, check-in times etc no journey should cost you more than half-a-day. That way, you can build places like London, Paris, Berlin, Vienna, Madrid etc all into one vacation. Air travel is inexpensive if you book in advance with budget no-frills airlines, and cattle-class is good enough for such short flights. But you will need to travel light - baggage charges on budget airlines are all out-of-proportion. (Perhaps plan your itinerary so that you can stow some luggage at a place you'll be returning to at the end of your vacation).
We're not city-lovers, our preference is for the freedom of the road - to rent a car and to some extent make it up as we go along. For dramatic scenery consider from Venice to the lakes of northern Italy then the old Alpine passes to Switzerland & Austria, mebbe even into the Bavarian or Black Forest quarters of southern Germany. Those old Alpine passes are snow-bound til well into May (so watch your timing) but they're dramatic and traffic-free - trucks and business travellers use the modern motorways & Alpine tunnels. Check Googleimages for example like Furka Pass, Susten Pass, Gottard pass.
Lots of other options too.
Yes, as others have pointed out, the danger of building in too much. That's one reason why we prefer travel by scenic routes - the journey is as enjoyable as the destination, and a leisurely ten-hour back-roads drive is waaay more interesting than a five-hour dash on a fast & boring main road.
Just my thoughts
Anyone who looks like their passport photo is too ill to travel (Will Kommen)