"It makes you feel free."
How I did it: I started on a dirt bike and just zipped around some empty property for several weeks, getting used to working the clutch, shifting gears, and maneuvering. Then I got a bike and my husband took me around the neighborhood several times. Then I took a class at the Harley shop and tightened up my turns and got very comfortable doing slow-speed maneuvers. Then I stopped riding for a year and a half. Then I got on again and rode around the neighborhood, went on a long ride out to one of our gorgeous local parks - the Volo Bogs. Then I went to Sturgis and rented a bike twice as big as my usual bike. And I rode.
Lessons & tips: It's not hard to ride fast. It's hard to ride slow. Practice riding slow and getting used to maneuvering around a parking lot. Get comfortable shifting into first gear. Practice it over and over and over and over again. Get used to letting your bike's engine do the work for you - DON'T rely on walking your bike, you look ridiculous. Get used to making sharp turns at low speeds - those are the tricky ones, not the long easy curves. Learn how to ride in a tiny space without putting your feet down except to back up. Learn how to ride without sticking a foot out with the expectation that you will catch yourself if you tip over - if you tip over, that leg will now be trapped under 800 pounds of motorcycle. Really knowing how to ride a cruiser is about being able to handle your bike at slow speeds, not fast ones.
Resources: Take a few classes. If they stick you on a tiny bike that has no relation to the bike you will actually be riding, find a new class. Take the advanced course. Buy some cones and replicate the course in your own local parking lot. Practice as much as possible.