What Should I be Looking At!?

[Manson_Brigg]

Hey all!

I've been sailing small sailboats since I was 12, but as I approach the end of my college studies, I find my self more and more drawn to a life of adventure.

So I have this idea I got from a blog i stumbled upon called hobo-sailer. He bought a cheap 32' boat and has been sailing the Caribbean and New England for like, 6 years or something. I only have about $25,000 in student loans to pay off and I'm thinking that once I pay it off and am effectively debt free, I'd like to spend 6 months in the Caribbean sailing the islands in a cheap, but reliable boat, preferably in the $500-$6000 range. I see a ton all over the place on craigslist and I've found a few blogs talking about their experiences, but none of them have the planning stage really mapped out. So my questions for you fine gents and ladies are these:

What boat would you recommend I look into? Used or new?

Where are some resources for this kind of an adventure on the web that I may not have found yet?

Have you ever tried a pro;onged island hopping cruise and what did you like or hate about it? What things do you recommend or highly NOT recommend?

Is it worth it going it alone or should I try and convince a friend to go on this crazy escapade with me?

Any advice, tips, etc are appreciated. Also please note I am not anticipating all fair weather and drinking rum on a hammock, I know there are downsides to living on a boat, (mildew, rain, shower-less-ness at times, maintenance, etc ) so know I'm not seeing myself as a romanticized Jack Sparrow the whole time. I'm in it for the adventure, rough times and all)

You all rock, thank you for any tips and advice you can throw my way! I got probably two years before castoff so I want to learn all I can in the meantime!

[zeehag]

there is nothing new in the up to 6000usd range. is all used.and some used way much.
if you dont know what you want to do , you cannot figger out what you want. if you dont know what you want, how can anyone decide you .....is all your life.

[JK n Smitty]

Ouch. I think the budget of $500-6,000 is going to be your limiting factor. If you keep your eyes open you might be able to find something in the 25-27 foot range that will be usable for that trip.

These two girls are doing the great loop in a Cal 2-27. They spent a couple of months in the Bahamas but didn't go down to the Caribbean.

My advice is to go before you start worrying about the student loans. Paying off $25K in student loans isn't quick or easy. You will pulled into the real world before you ever pay them off and you will never go. I graduate with $25K of student loans 15 years ago. Still have about $10K of it left and that is with stepping up payments over the last 2 years to get them paid off before we go. Trust me, it's definitely easier to pay them off when you are further into your career and make more money.

As to practical advise, I don't have much to offer. We are in the process of selling everything to go do what you are talking about. We weren't smart enough to think about doing it before we got a house, cars, more debt, etc. We do have some planning stuff in our blog. Some might be helpful to you.

What would be wrong with your cheap 32' boat for doing this trip? Investing $5K to fix up a boat might be a lot more manageable then trying to buy another one and fixing it up.

[Stu Jackson]

Find "Twenty Small Sailboats to Take You Anywhere" by John Vigor.