Before we move on to Step 2 of planning the trip, there are two things you need to have in hand. First, get thee a guidebook: I don’t care which one you choose just so long as the book’s style matches your style. We go for Rick Steves because he believes travel is a matter of spending time in someone else’s home so be nice. Walk into your local bookstore—yes, you want a hardcopy—and you’ll see a staggering array of travel books. I guarantee you will find one that speaks to you. They are all reputable. Some are for the younger traveler, some are for the older and some are for those visiting from other solar systems.
The second thing you will need are blank calendar pages for the month/s you plan on being on the road. With great big squares for writing a bunch of stuff, scribbling over, making stabby marks and writing more. You’ll also benefit from an online spreadsheet but it’s not essential at this point. The dementedly organized may wish to pull out that multi-colour pack of highlighters bought when Zellers when out of business. It is not necessary but what the heck, it will look pretty. 
The third thing (yes, I lied) is a big glass of whatever fortification required when no one else in the world makes sense.
There are two basic approaches to how to cover ground while traveling. Many people like to find a hub that is within a 2 hour bus/train ride of several other places. That way there is a home base, nothing more than a day pack to cart about and a familiar bathroom at the end of the day. This works well if you are planning a trip within one or two countries and really want to explore these regions.
The other method is what I like to call the Mongol invasion strategy. The plan is to cut a wide swath through several destinations going from one end of the continent to the other. Some cities will be visited for a few days as they contain more wealth and opportunities for pillaging while others get a quick visit, hop off the horse long enough to sample local cuisine, woo a few local maidens and then rise early to move on to the next place.
Both have their advantages and advocates, it’s a matter of personal taste.
So, got your guide book guru? Good. Got your calendar pages? Good, yes, the colour coding chart is lovely, dear, well done, here’s your star and a gummie bear. Big cup of tea? Not tea? Fine, on the rocks or with a squeeze of lime, whatever gets you through the next few hours.
Did I mention the credit card? 