Difficulty: Moderately Easy
Step1
Determine your riding style. Harley-Davidson has a wide variety of models for all riding styles, so determine whether you would like to have a cruiser, a custom bike or a sports bike. Knowing your riding style is important, as it will directly affect your riding experience.
Just as an FYI, a cruiser is for your longer road trips while your sports bike is more for sipping around town. A custom Harley is strictly for looks--it'll take you on those road trips and around town, but depending on how you trick out your custom bike, it could be somewhat uncomfortable to ride for extended periods of time.
Step2
Recognize your riding needs. Buying a motorcycle that is too big or too powerful may ruin a riding experience or result in injury. Think carefully about size, power and what conditions you plan to be riding in. This will help to limit your choices, when it is time to choose your model.
Step3
Choose which Harley model is best for you. Now that you know what you want and need in a bike, decide which models you would like to take for a demo ride. Of course, you'll have to have a licence on hand that shows proof of your motorcycle-class licence. This licence is different in every state so you'll have to take a written test as well as a field test to get one.
Step4
Decide whether you would like to buy used or new. If you are interested in vintage models or a fixer, than used would be the way to go. If you are more concerned with using your motorcycle simply as a reliable mode of transportation, you may wan to consider buying a new model.
If this happens to be your first bike, you might want to opt for a used bike. Simply because you will scrape it up a bit--it happens to everyone, no matter how careful you are.