I am by no means a woodworker, but I have been able to figure out how create pretty wooden signs with a dash of calligraphy! I could never have figured it out without trial and error, expert advice and wisdom (most from my mom), and probably six different types of stains and sealants. It's taken a few years, but I am happy to say I've finally got the hang of it! I'll preface this post by saying that wood is definitely the most challenging surface I have ever worked on. It is very unforgiving, in my experience, and there are so many confusing options when you choose your wood. Preparation and planning is EVERYTHING! A little research doesn't hurt, either. There is no returning after you stain, so make sure you're set on the color and you've fully prepped/conditioned/sanded/dusted your wood. There are a lot of steps, but if you can do that well, the end result will be so lovely.
My favorite brand of stain is the Polyshades by Mixwax - it's a stain and polyurethane combo. I have tried countless paints, paint markers, both oil-based and acrylic-based, for white calligraphy on the wood. I'm listing some of the basics I use for wood lettering and prep, with the images linked below. Hope this is helpful for your woodworking endeavors!