Not as young as I used to be

Prague to Dubrovnik is adventurous for any age; and challenging logistically. I am about the same age and I have done my best to slow it down a little and enjoy the places in between. I tend to find a comfortable place and then do side trips. My "hub" for this is Budapest. Up until the demise of Malev Hungarian Airlines Budapest was ideal; now it's a tad bit harder but you can still do some exotic travel by air for under a few hundred round trip. Some countries I have flown into and driven back (been driven back) and that is an excellent way to see some unique and wonderful places, but the cost is somewhat higher. You might look at apartment rentals in lieu of hotels. The apartments can at times be quite nice and a fraction of the cost of hotels. You can save a little more money if you cook an occasional meal (but I never do beyond the occasional breakfast). Eurorail passes work well but you have to stick to a country or set of countries and some of the train rides can be pretty long and pretty tedious. On some of the overnight trains there are some safety issues. But its an option. Choose countries that are not on the euro. Right now the Czech Republic (outside of Prague), Slovakia, Hungary, Bulgaria, Romania and Croatia are real bargains. Much of these countries still exist in a state reminiscent of the 1940's but it wont stay that way for long so they are on the top of my list to see before they change. You want to go "to the sea", Dubrovnik is beautiful, by Varna is also an option and much more exotic and less expensive (but granted not beautiful in the same way as Dubrovnik). I can assist if you are crossing through Slovakia, Hungary, Romania or Bulgaria, and I have a few comments on Vienna as well. Happy Trails where ever they take you.

Suggest you buy Rick's Prague and The Czech Republic Guidebook. Loads of pertinent information and recommendations about costs, public transport, restaurants, lodging, etc. That will help you strategize your itinerary. BTW none of us are as young as we used to be. Still reeling over the notation of Senior on my Tower of London ticket.

James, Slovakia is on Euro, but you are right, comparing to western Europe it is still a bargain.

Bad English: Choose countries that are not on the euro (PERIOD). (IMPLIED "Also,") Right now the Czech Republic (outside of Prague), Slovakia, Hungary, Bulgaria, Romania and Croatia (probalby outside of Dubrovnik) are real bargains. And I left out that i have heard Slovenia is stunning for the cost.

How many days between the 2?

We did all of the booking by email before we left. We always had a place to stay each night. Prior to going the next day, we would email. The only problem was Split, where somehow I lost the info, and we were there at 6:30 PM with no idea where the room was. Worked out OK - we went to another tourist room place we saw as we were driving, and they knew right away who our connection was, and contacted them. Most of these tourist towns are helpful to tourists. It sometimes took me a week to find a place at the right price - but I was going with 5 (me, wife, 3 grown children), and I wanted to spend under E125/night, which we did all but one night.