I have been making these little font wreaths in Adobe Illustrator for years. And look, firstbornmultimedia.com has gone and made a useful little ap with the same idea!
Pick a font, any font. Pick a letter, any letter. Use the rotate tool. Usually rotating 45 degrees, but you can experiment with that as well. Rotating and picking different center marks on the letter for rotation will give you a variety of looks from one letter. Below see of the variations from some boring font for the letter "y". I found that the most elaborate scripts make the most fun wreaths!
I love Boston.
2 hours ago