How to best map out all the places within a city you want to visit

Here's a really radical thought: For the airlines, all you really need is the reservation number (which you don't really need) and the departure dates and times. They will all fit on half of one side of a three by five card. The Rome and London hotel stuff will finish off that side. Three places in Sicily will finish up the other side. Buy a plastic coated map for London and Rome that will fold up and fit in your pocket. Do something similar for Sicily - - you haven't said how much area you'll cover. Alternatively, you can pick up paper tossable maps from the TIs. GPS doesn't work too well walking around in cities. You'll burn through a data plan in two seconds. An international voice plan is a good deal. Wifi works. I've been on the road for the better part of the last seven weeks, covered quite a few countries and miles, and never once flipped on cellular data. Go back to the nineteenth century, it's a lot easier. I don't care for three by fives since they're expensive. The back of an envelope works just fine.

I wish there was a Like button for Ed's answer...

I agree with Ed too. I don't overload my itinerary, first of all, so there's no reason to plan down to the hour. I pick two big things a day to see (Notre-Dame and Pere Lachaise cemetery in Paris, for example) and because I have time, I don't care if they're far apart. In Paris last month, my sister brought her old iPhone 3G with the SIM card removed so it became like an iPod Touch, and to our surprise we discovered that the phone had GPS when we were out and about. (It was helpful but not THAT necessary.) Wifi was as advanced as we got on the trip - no smartphones, no car GPS. Somehow we managed to find and see everything on our list with "limited" technology.

We had a Garmin GPS with us our last trip for driving in Tuscany (VERY helpful!). When we were in Rome and Venice we pulled it out a few times to see if it knew where we were, out of curiosity, if we were in an open space, large piazza, it found us just fine, if we were in narrow streets it lost us and would catch up again at the next piazza. For Rome, not very useful. We also carry a laminated map with us for cities, look for our general direction of travel to what we want to go to next, put the map away and head off, looking for the most interesting paths that are in our general direction. We try to only plan one or two things for a specific day and then keep in mind the other things near it that we may hive time or as well. Try to keep some flexibility though, some sites will take you longer than you planned and some may take less, you never know until you get there! We do use our iPhones heavily for audio guides and podcasts for some of the sites.

Gotta love those 'radical thoughts'... totally agree, after all, isn't this supposed to be a vacation? It's so easy to just go with the flow, use a paper map, and if you get lost... ask someone? Always works for me...although I do use my GPS when driving, but I think its so much more enjoyable to leave as much technology out of the picture as possible...but I am a bit of an unorthodox traveler.

I also like to plan no more than two major sights per day, one in the morning and one in the afternoon. I like to keep a few "good to see if I have time" sights in my back pocket just in case I find myself with extra time. If you schedule too tightly, you will always be trying to catch up - and you will always lose some time for transportation connections, ticket lines, traffic, etc. Building in lag time lowers the stress level a lot.

TripIt is a great app that doesn't rely on data once you have everything synced, it's a handy place that uses your email notifications for plane/hotel bookings and saves them to one place on your phone. No work involved.

To answer your question about the GPS, yes, you can purchase GPSs with European maps preloaded, in addition to US maps.

The idea of using new technology is better in theory then practice. As stated GPS doesn't work well in cities, especially with tall buildings and winding medieval roads, you'll have to walk a block to figure out if you are walking in the right direction. A compass and paper map are a better option. Planning everything online is nice, until you have to change plans and can't get Internet access and don't have any airline phone numbers to call. Your smart phone on wifi is great for Skype calls home when you can get decent Internet access. Trying to go high tech while being a tourist isn't all it's cracked up to be. Take paper back ups of reservation numbers. Paper back guide books with the sections torn out (to carry easily) can help find a decent restaurant while on the go.

Re: Ed's response
Like.

I like to visit a TI when I arrive in a place. They'll give you a local map, update you on opening/closing times, and know about any special community events/festivals/etc. that are happening during your visit.

Pick out the site that interests you the most, then go to Google Maps. Find the other sites, and map out a circular route. Trip Advisor is good with this, as all the attractions listed for the various cities have a Google Map listed too. If you are in a medium to large city, go on a walking tour or bike tour that will take you to most of the sites you want to see. This is the easiest way of all, and you will leave the city with more of a sense of having learned something about the city and its' history.