Hi all,
I'm new to the forum and new to the world of sailing, so take it easy on me

.
So this is just a brainstorm and before I start seriously looking into it I just wanna figure out if it's even a realistic possibility.
I'm 19 years old and own my own and run my own landscaping/ hardscaping business, the winter is far from exciting for me. I usually only have snow plowing work but I don't depend on that because here in PA some years we hardly get any snow.
So here's the idea, to buy a sailboat and take a couple months off this winter and live on the boat (sail the east coast). I figure the time I would have to work with would be from early december to late february.
My sailing experience is limited. I own a small day sailer that I take out a few times a year, I feel confident on it, but obviously that's a totally different world that a 25-30ft boat. So sailing lessons and lots of reading practice ect would be expected.
I wouldn't plan on doing it alone, my girlfriend would definately go with and bringing her dad along is also a though. (he has a small amount of sailing experience on larger boats).
I'm mechanically enclined, grew up on a farm where if I didn't know how to fix it I figured out how.
I think the biggest problem, at least that I see right now is finances. I figure I could have around 5,000 to do the trip after I bought the boat. I'm figuring around 4,000-6,000 for the boat. So basically I figure right now I can have around 15,000 by the end of the summer to spend on the adventure. Obviously I would be buying the boat sooner and getting it ready and spending money and time to learn to sail it, and possibly take a few small trips before the big one to get ready.
Just looking for opinions, ideas, and advice. Is this a possible adventure if I put my mind to it? Major problems I'm not seeing ect..? I'm afraid if I put this off a few years I'll have too many responsibilities, right now my bills are low and the time is available.
Thanks in advance,
Austin