Basic Strategies

Price shop. Use a wine search tool like wine-searcher to find availability and the best price in your area. There are others but I happen to like the wine-searcher search engine .
Ask questions. This may seem obvious but a wine shop owner or a sommelier (wine steward) in a restaurant should be there to help you. Tell them what you like, what you don’t, and see what they recommend. Advice is free.
Always ask to see a wine list at a restaurant. They are great sources of information for becoming familiar with wine regions, wine types and sometimes include descriptions.
Become a regular. Stores will often offer a preferred customer discount.
Shop at stores that discount by the case. If you don’t need a whole case work with friends on a “group buy” and split the discount. (Be careful- very large discounts could indicate that you are being overcharged per bottle.)
Find well known stores on the internet that offer free shipping and/or don’t charge tax.
Try before you buy (if possible), especially expensive wines. Know what you like and participate in free tastings to reduce disappointment.
Try different wines by the glass at restaurants, and wine bars, before committing to purchase an entire bottle. (hint: kindly ask how long it has been open) They will know you are serious and may suggest something else.