2-3 weeks in Italy & Switzerland

The easiest way to plan a trip is (wait for it) seeing the trips that others have taken. So that means looking at a Rick Steves guide, and a Fodors and a Frommers, and looking at their suggested itineraries.

Then find 2 or 3 major travel companies (like Globus) and see what they recommend. You'll find a consensus of things that these folks think are important enough for everyone to see, then knowing your tastes, needs, wants etc. you can pick and choose from what they offer.

In Europe, you should train. But the trick question is, should you get a railpass? That's one that you have to research on your own, the folks at Rick Steves railpass center can help but you have to do the maths yourself.

2-3 weeks is hardly enough for the Italy destinations you list, much less Switzerland. Absolutely allocate 3 weeks (or more) and spend two in Italy. In two weeks you can do Rome and north, so skip Naples and Capri. Rome, Florence, Venice, and Lake Como OR the Cinque Terre would be enough in two weeks. Otherwise all you are doing is packing up and moving every two or three days. There is a high cost in both time and money to try and do too much. I am no expert on Switzerland so maybe someone can recommend a one week Swiss itinerary for you. Oh, trains by all means! No need to drive.

With only a very short 2-3 weeks, you won't be able to see every place on your list so you'll have to be selective in planning. With such a short time frame, you'll realistically (IMO) be able to cover 7-10 places in both countries. Keep in mind during your planning that each change of location will require a minimum of about half a day (and sometimes longer).

I'd suggest skipping Naples, Capri (the Blue Grotto) and the south, Pisa (you can do that as a day trip) and Milan for a start. In Switzerland I wouldn't bother with St. Moritz, and Zermatt is "questionable". Some other places you might consider are Lucerne, Bern and especially the Berner Oberland.

Staying at least two nights in each location (and three nights in some) will provide some time to see some of the local sights. I try to avoid one night stops whenever possible, as they usually only provide a few hours to look around.

Flying into Rome and working north is probably a good idea at that time of the year, as the weather will get warmer as your trip progresses. It would be a good idea to pre-book hotels in each location (especially the Cinque Terre) as June is the "spring shoulder season" and it will likely be very busy in Europe.

Good luck with your planning!

I like Ken's suggestions for streamlining your destinations. You don't need a car for anything on the list; all are well served by train. Plan the destinations first, knowing that trains will get you to each next stop in less than a day. How to Look Up Train Schedules Online gives you the DB train schedule link and tips for using it, although you don't need to get that detailed now. For the Milan-Varenna-Tirano route (Lake Como to Bernina Express), see schedules at www.trenitalia.com or www.trenord.it. See also my advice to another reader today about Swiss Passes and Italy Passes.