Dingy racer looking to cruise :)

[Lazr]

Hi all! I've been sailing dinghies since I was six and racing since nine. Mostly on San Francisco Bay in opti's, el toro's, FJ's, 29ers and lots and lots of time on lasers. I moved to Santa Cruz, CA last fall (Oct 09) and have been racing my laser down here, but also getting into the keelboat racing scene, campaigning on SC27's and Moore 24's mostly doing foredeck and tactics. The racing is a blast with lots of nice, fun people around in those fleets too. I'm working on getting a position on some larger boats that'll do some coastal passages to get some more serious open-water experience under my belt.

The reason I joined on here is that I'm planning on leaving on a long-term trip in a few years and want to gain a little insight into what I'd be getting myself into. My plan is to sail from California down to Peru/Chile and then out to the South Pacific Islands and maybe continue on or sell and take up the island life for a while. (One option I've considered as well is selling in Peru/Chile and crewing for the leg out to the islands) I'm an adventurer and a big surfer as well so my trip will definitely be a surf expedition at it's heart and that might make it a little different than your standard cruise, but I think I have a lot to gain from reading and posting on here.

The boat I'm currently looking at is the Pearson Triton 28 as they're affordable and easy to find around the SF bay area. I'm still very open to other boats too like a Nor'sea 27, an Alberg 30, the other 27-32ft Pearsons, or an Albin Vega 27 to name names. A small boat should be fine for me as I've lived out of my camper shell on my truck for months without feeling too claustrophobic. I'm planning on bringing my dog along and am a little concerned about having enough room for him to be comfortable.

My dog's ~40lbs and will be around 4-5yrs when I leave. Also I'm 5'9" for a berth-size/headroom reference point to work off.

Am interested not just in boat selection, but more of a bigger overview of what goes into a trip like this. Costs, logistics and really anything anyone feels might help me out, even if it's something I might not want to hear...I'd rather have someone tell me now, than figure it out for myself at a bad time. Feel free to point me to other threads/websites/books/resources that might be useful.

Thanks in advance everyone!