Ive Caught The BUG! HELP!!!

[PBO]

Ok I've caught the sailing bug after talking to a friend of mine who lived aboard for a couple years in his 20's. Its all I've thought about for the past week. I understand there's a lot of work ahead of me and this is no small undertaking. Let me tell you my situation and tell you what I envision and let everyone give advice as to whether or not this is possible to pull off.

Ok first of all I'm 24, I work for an airline in Puerto Rico, so my typical schedule is 3-4 days on, 3-4 off, with the ability to arrange a 5-7 day off period once a month, 2 vacation periods a year which would end up being 14 days off each. I also get free air travel.

So my plan is to buy a sailboat and live aboard based out of Tortola preferably in Cane Garden bay so I can jump off the boat and go surf in the morning, day sail when there isn't any waves, and on the longer vacation periods cruise around the Caribbean, stopping in st marten ect. Catch a flight back to PR when I have to work, and I'd be gone for 3-4 days each work period.

Problems, that I've thought of are as follow,
1)I dont know how to sail, thought about possibly going to one of the week-long programs, or trading services, flight instruction, kitesurfing lessons, possibly free airline flights for sailing lessons. Any other ideas?
2) I dont make that much money essentially total budget 2000ish a month, so my financing plan would be to take out a loan make monthly payments on the boat. But I also don't have any idea the costs of mooring, docking , or anchoring in the Caribbean. Do you need to be docked if your living aboard(for waste disposal etc)? Any other unforeseen financial dilemmas im missing?
3) Can you just leave your boat unattended for 3-4 days, I assume theft and other issues would arise?

I'd prefer to just jump right into the sailing without lengthy maintenance to a fixer-upper what can I expect a used/livable seaworthy sailboat start at?

I'm sure i havent even thought of/left out some other problems or possible deal breakers, feel free to enlighten me. My apologies if this all sounds naive I'm still as green as it gets when it comes to sailing. Thank you for any replies.

[jkirstein]

Cool. Go for it. When you're in Cane Garden Bay, please walk up the road and over the hill to Brewer's Bay Campground (please take a can of dogfood) to see my two favorite dogs....Spot and Flipper. You'll recognize them. Then ask the lady at the campground if she's interested in selling the place.

If she is, please reply to this post.

Thanks.

[Ex-Calif]

My advice is to not finance, buy as small a keelboat as you can afford.

Making payments and paying boat morring and maintenance on $2000 a month is optimistic.

Our boat is only 27 feet but we reserve USD$400 per month for costs and maintenance reserves.

A 25-27 foot boat would do what you are asking. For reference we got our boat "cheap" but have but the same amount into her in over 1 year of sailing due to "rolling" retrofits.

An alternative, is to get a dinghy. Much cheaper and will get you out on the water at a fraction of a keelboat cost.

[Therapy]

Read everything here for a year or so.
Including the links.
Start with today and work backwards.

[camaraderie]

The first thing you need to do is discard your notion of living aboard in Cane Garden Bay. The closest SAFE harbor for you will be Sopers Hole. The reason Cane Garden is suitable for surfing on the point...is the reason it is unsuitable for marinas and permanent mooring.