I break it down into three or four areas.

• get there
• sleep there
• get around there
• get home

that's the major stuff I worry about for any trip. The rest will fall into place even if I don't do anything else. There are always things to see, places to eat, wine to drink, etc.

So I get the airfare first. Then the hotel, usually with the chain I'm with, but not always based on the location.

Getting around may mean renting a car, getting passes for local systems, etc
Getting back is usually arranged with getting there.

For the rest I'll look at guidebooks, I'll search what other people have said over at tripadvisor (which I've found some excellent restaurants on for example) and some general internet searches.

And of course, the totally invaluable information available using the search function here, and asking in the appropriate forum, and in just asking. Ask for a hotel in Venice on most any forum and you will get some answers. Ask here, and you will get the owner's name, who to ask for, which room, etc.

Tivo is also great if you have the time, set a keyword search to automaticailly record any show that has that as a keyword for places you are visiting. Most of it will be garbage to delete, but you may get some real gems in there, travel shows you never heard of on channels you didn't know you got.

But don't sweat the details at all. Don't overplan what you are trying, it sounds like, to be a relaxing trip.