For cheap and most maximize free and easy trips here are my suggestions:
1. 6 months before:
Know which part of the world you wanna go and
search for that cheap no frills transportation, either air flight (budgets) or train or buses. Usually they will bombard the media with cheap cheap cheap deal (really cheap like 70% off). Remind yourself about Visa rules.
2. Do your homework, find out about your destination sites to see and match it with your interest. Then find a hotel near those areas.
3. Google your hotel to find a very good deal, no need to rush, just wait for the hotels to go on sale, have some backups.
You have to go through a lot of hotels website, some local company sometimes offer better value for hotels in its city. But I know some people like to play safe and booked only from world wide famous website.
4. 4 months later:
Booked your hotel, (if they were on sale 6 month before than it's a good thing you already booked them)
5. Start planning the details, either want to visit the cities nearby or daily activity. Start hunting for stuff you might need. Like going on winter find winter suit (always buy on sale since it's not daily clothes after you got back), mosquito repellent for countries that known for dengue, etc
6. Know your destination, for their local laws, tradition and culture. Look for their tourism board and ask for maps (usually they'll send you a free copy or just print it). It's useful especially when you really blind about the area or language they are talking. Guide book from tourism board include simple language guide, like 'where's the restroom?' (very important). Some countries also offer free local guide, check them out.
7. 2 months before:
Confirm everything, from hotel, flights, other transportation, visa, money, currency, living cost, stuff you need, vaccinations, doctor's recommendation on your personal health like spring in Korea means lots of allergy for some people, and so on.
8. Days before:
Check the weather, so you'll be more prepared and less surprises. News also important, some political issue might even have impact for tourists, or natural disaster, so keep your eyes open.
9. When thing go not exactly like you want:
It's okay, enjoy the ride and learn from it. You might have an adventure of a life time.