See if you can get ahold of Melanie Neal. She is the daughter if Tom Neale and lives on a 28 foot boat in south Florida. Melanie and her sister grew up on a sail boat and Tom and wife are very well known sailors. He wrote (and still may) many, many articles in Cruising World.
If you get the newest issue of Cruising World, get the email address of the editor and see if you can have a message forwarded to Melanie. SHe is about your age and would be a awesome source for information as I imagine she knows more about sailing and cruising than 90% of the people on this forum.
Other thoughts are to check out an all woman sailing school. See if you can talk to some instructors (who would be women) that would know the females there that might help.
I would really hesitate hoping on a boat with a group of guys heading south for the sunset. I will share with you a very, very true story:
We lived aboard on a marina in S Florida and always got out and walked the docks with our 2 year old. He was very friendly and was loved by everyone there. There was one gentleman in particular: He was an older gentleman, nicely kept, probably in his mid to upper 50's He would offer our son candy. I often stopped to talk to him and helped him out on a couple of projects. Turns out he was a repeat child sex offender. I want to stress that he did NOT do anything to us or child... but I would never, never have guessed. He was living on his boat, because on your boat most marinas will not run a background check.
Our new owners did.
PM our write back to us and let us know how it is going. If you are having trouble getting through, let me know and I will see if I can help. I do NOT know the Neals, but have found that the staff at Cruising World has always been helpful.
Best to you.