Driving

Get the Michelin Green Guides for all three countries. Use the maps with their hierarchal ratings of the merits of places and connect the dots. Study up on the cost of getting a car in Spain a dumping it in Italy. You might want to use those high speed routes to get it back to where it came from. Just for grins, you can make it from Milan to Barcelona in daylight in a single day in the summer, but it ain't much fun.

Melissa, You'll probably find that there will be a huge charge for renting a car in one country and dropping in another. Although you may want to "meander", I'd suggest using a combination of public transit (high speed trains) and car rental, as that will be a more efficient use of your limited travel time. Note that for driving in Italy, EACH driver must have the compulsory International Driver's Permit, which is used in conjunction with your home D.L. Failure to produce an I.D.P. if requested can result in fines on the spot! You'll also need to be VERY careful to avoid the dreaded ZTL (limited traffic) areas which exist in many towns in Italy (large fines!). Good luck with your planning!

Spain also requires the DLP.

This link is an itinerary we had originally looked at driving (we're choosing instead to drive, and ended up doing Munich to Barcelona instead of Italy) - it was a great startoff for planning my trip! http://goeurope.about.com/od/suggesteditineraries/l/bl_mediterranean-itinerary.htm

It might be worth while to take a look at the Via Michelin web site. They at least give you the option of fastest, shortest, no tolls or scenic for the routing. That combined with some off the beaten path destinations from guide books should work out. Don't forget a GPS and a fairly large scale paper map just in case 'meandering' turns into 'lost' which is not that hard to do. Also don't forget you need IDP's in both Spain and Italy. Have a great trip.

Melissa, as one who meanders on all of my trips to Europe, I recommend the Via Michelin website and a good paper map also. I have always returned my rental to the starting point rental agency so I can not comment on the drop off charges. Via Michelin gives you a good indication of transit times and costs. It also allows you to pick your own way points. My last trip lasted 10 days and the route was: Frankfurt - Innsbruck - St. Martin Lupari (It.) - Venice - Bologna - Milan - Lumschwiller (Fr.) - Gunzviller (Fr.) - Frankfurt. We used a paper map and a GPS. Get a good map that shows local roads along with the more traveled autoroutes. 3 weeks is plenty of time to cover your route at a leisurely pace.
Good luck!

I just got an estimate of the fee to drop a rental car picked up in Italy and left in France from Autoeurope. It was 250 euro + VAT, which the agent thought might be as much as 20&. In another words, we're talking about the neighborhood of $400. Only you can decide if it's worth paying that vs the cost and hassle of other options. I was seriously considering it, but I worked out that by doing a figure 8 itinerary, Nice - Tuscany - Provence - Nice, we could save $1000 over any of other three options I had worked out, which all were going to run between $1500 and $1600. No-brainer! I'll just point out that in my researching I found that cars picked up in Italy were much more expensive than those picked up in France. Don't know where Spain fits into the picture. One thought I had, though, was that you could avoid the foreign drop fee by taking a train from the last possible Spanish town for dropping a car to somewhere like Montpellier, and pick up a new car. Drop the French car in Nice and take the train to San Remo. Get a new car in SR. All sorts of issues will impact what is the best course. Where are you going in Italy? How many people? How much luggage? How much hassle can you tolerate? The Autoeurope people are very accommodating as far as giving you estimates for various rental options and associated fees.

I normally go back and forth between guidebooks, looking for interesting things to see and do, and viamichelin.com, to see if it would be a workable driving distance. Picking up and dropping in different countries can also be needlessly expensive though it may be the best alternative. Try testing the price of dropping before you leave the country and picking another up on the other side of the border. Sometimes that can save a few hundred dollars.

Hello everyone - thank you all very much for your information. It has given me even more options that I'd not thought of before!