Using Spain as an example, the first thing to do is to read every guidebook possible. I like to start with Lonely Planet. There are certainly others. Make a limited list of things you wish to see. We have the luxury of more time so we often will take a ten day commercial tour and then rent a car for a week or so. It may be just as easy for you to check railroad schedules as the trains in Spain are comfortable and leave the driving to someone else. Using taxis is often less expensive than parking.
Taking your list give each a priority and how much time you wish to spent. Say your tour was of Madrid and Barcelona and you now wish to see Andalusia from Granada to Seville. That is realistic in a week including a day long trip from Seville to Madrid to catch a flight. Draw a map and put down distances and times. I live in California and it takes a very long day to go from one end to the other and still not see anything at highway speed. Spain is much smaller and places are closer.
Check the schedules and plan the trip. Be sure to figure in surprises and last minute ideas. I usually will reserve the first and last days in a hotel or bed and breakfast and make lists of likely places to stay the other days. No need to cancel that way. Now, find someone who has been there and asked for their ideas. They may be helpful and remember you don't need to follow their suggestions.
Some people will not be comfortable with planning their own trip. Then, take a tour and plan to take your own adventure next time. Warning: your High School Spanish will not work well in Spain but English is spoken most everywhere.
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