Use free tests, such as the one offered on FindYourSpot.com or the "Which city Fits Your Best?" quiz on Quibblo.com, to start a list of areas where you might relocate to.
Focus on resources that fit your needs. For example, you can add or eliminate a resource such as the annual Forbes list of the best places to live in the world based on whether you plan to stay within the United States. You can also use only parts of reputable lists, such as taking only cities from CNN Money's list of the best places to live that fall within a population range that you prefer.
Talk to people you know who live or have lived in the areas where you're thinking of relocating to glean more insight into their day-to-day experiences.
Research the weather, population and economy of the various cities on your list. Your local library can offer resources to help you, and you can visit each city's website.
Consider the future conditions of the cities you are considering. For example, Kiplinger ranks the cites that it expects to fare well over the next decade, factoring in conditions such as job growth and cost of living.
Read a few copies of each city's local newspaper. You can learn a lot from a local newspaper, such as weather, crime rates, politics and available jobs from the classifieds.
Travel to each city on your list and try to spend at least a few days in each. Pay attention to the vibe you get while in the city. It can tell you a lot about whether you'll be happy there.