Planning to Live Aboard from Massachusetts

[drummingpariah]

Hello! (ahoy?)

A little about me
I'm finally coming to terms with the fact that I don't like staying in one place for extended periods of time. I'm 27, and for the past decade (rounding), I've moved pretty consistently every 6 months. I own two duffel bags of things, and a pair of computers (they constitute my income), and that's really it. I'm used to selling/gifting all my furniture, moving, and buying/receiving new furniture.

So after I came across a video about Teresa Cary and (kind of about) Ben Erikson recently, my interest was seriously piqued. They seemed to have found some magical way to put all my favorite things together AND travel around as part of everyday life. I did a bit more research, and more investigation, and a bit more reading after that, and with every new piece of information I uncovered, I became more and more interested in this lifestyle.

Complications
There are a few minor snags, like the fact that I haven't sailed in the past 15 years, and the largest boat I've ever sailed was a Sunfish, but I'm a big fan of learning on the job. I'll worry about those trivial setbacks once I'm in the water.

My Plan
Now, my initial (unrealistic, in all likelihood) goal is:
find+purchase a suitable boat (25' to 30' sloop of some brand seems reasonable, based on the advice I've seen others take), perform whatever essential maintenance is required, stock up on provisions and whatever gear I'll need, and start sailing South. I have friends along the East Coast that I can visit as I continue down, and I'm really interested in continuing on past the Florida Keys, crossing the Gulf Stream to the Bahamas/Caribbean Islands, and continuing South to meet up with a handful of friends in Brazil that I haven't seen in far too long. Ideally, I'd like to purchase a boat by August, and be on my way toward Virginia by October. If I take my time and am cautious of weather, I think I'll be able to make it to Brazil by February (for Carnival!), at which point I'll just turn around and head back (or sell/gift the boat and fly back, if I'm not in love with it by then).

I expect this will be seen as an overly-enthusiastic entrance into sailing, and that I'll be in over my head in no time, and I'm happy to listen to any advice anybody offers... but that doesn't necessarily mean I'll take it. I've made plenty of horribly ill-advised decisions in my time, and am proud of every single one of them. They have helped to make me a better person, living a more full life, and that's exactly what I'd like to get out of this.

A little more about me (you haven't skipped to the bottom to leave a reply yet?)
I'm a web and software developer and systems architect, and as such already work in a mobile setting. Ideally, I'd want to have reliable internet available but I'm very aware of how impossible that is, especially after leaving the coast of Florida. I can work around patchy Internet, as long as I can wrangle up a decent wireless signal once every couple weeks to upload my latest work. I've looked around for different onboard solutions, but haven't come up with anything. In the US, it looks like the East Coast is fairly well covered by Verizon's 3g and 4g networks, which will keep me perfectly content.

I consider myself a very mechanically inclined, logical person, and have fallen in love with several of my cars and re-engineered several others in the process. I run an automotive website called Driven Daily, and have become the go-to guy that my friends call when their mechanic can't figure out what's wrong with their car. Somehow, that paragraph was supposed to indicate that I plan to do as much of my own work as possible. I like getting my hands dirty.

Anyway, that's me, in a nutshell. After reading around on a few different forums, I decided this was the place for me. Most sailing forums seem to have a lot of very knowledgeable people lurking around, but I like the atmosphere here. Overall, you seem to be a logical bunch of interesting people who aren't afraid to respect illogical, passionate decisions. I have a feeling I'll like it here.

*footnote: My plan is very subject to change. It is not set in stone in any way whatsoever, and depends primarily on my bank account's status if/when I come across 'the perfect vessel'.