From Baltimore to Bermuda to Florida and the Gulf. Without a shakedown cruise.
I'd call that a real ambitious plan. Even if it wasn't hurricane season.
You might want to have a professional survey done to make sure "real good" shape is really solid, including the standing rigging
being closely inspected and perhaps replaced if it is 20 years old. And taking a 48-hour shakedown with your new crew, before you head off to Bermuda. Old boats have a way of surprising new owners, even when they ome from family members.