When I came out to my family as transgender I did it by doing small things, painting my toe nails, wearing pink, a lot of different things. Call it denial or whatnot but my family didn't pick up on the cues, being a family of mostly men they probably didn't want to hear it. I finally flat out said I was transgender and they laughed and didn't believe me. In fact it took them a few months before they believed me. I spent a couple months answering their questions, being humiliated and told things like I was going to hell as my family is very fundamental Christian. Yet they still didn't believe me...
Eventually about 3 months on HRT after not seeing my family for some time we all decided to do a family portrait. Thats the first time they saw me in a dress, with makeup on, using a female voice and allowing my natural feminine body language to take over. After that point they started realizing I was serious. Fast forward a few more months, I transitioned at work and went full time, updated my name and legal information and so on. They finally realized I was serious about it all.
It is difficult, it is embarrassing, you will cry before, during and after you tell them. But you will be okay and you will move on and realize its not that big of a deal.
If anything my advice is to just jump in, its like swimming in a cold lake, you can rationalize the courage all day but it almost takes a certain degree of insanity to just jump and and let everything else take care of itself. Best of luck.