As someone who has participated in rallying and who is organizing one to Bermuda right now, I think Billyruffn's post is an excellent description of the pros and cons of doing a rally.
One thing I do take issue with is what he has to say about the cost. For what you get, the cost is not expensive at all. For instance, in our upcoming rally the cost is $1,999, which includes dockage on both ends. If you were to go out on your own and buy "retail" the services we're providing, you would spend more than that. And that does not even take account of the expert advice you get along the way (i.e., inspections, gear lists, prep lists), avoiding the hassle of having to make the myriad arrangements yourself, etc. Now, if you don't want those services and if what you want is to sail by yourself, get only publicly available weather, interpret it yourself, and anchor once you get there, then certainly you would spend less money, but if that's what you want then you just don't want a rally. I'm biased for sure, but I think rallies provide excellent value and they provide a great mechanism for stretching your legs.
Another thought, which billyruffn does highlight, is that the safety in numbers thing is real. I disagree with those who say once you get out there you're on your own anyway so rallies offer only a "false" sense of security. Of course you need to be self-sufficient and a rally is not a guaranty of safety, good conditions or good judgment. But, the ability to call someone for guidance or help, that someone is tracking you and knows generally where you are, and knows to come looking for you if you don't check in, are real safety benefits, even once you are out of sight of land or any other boat. Obviously if your boat sinks in minutes before you can activate an EPIRB and get into your raft, there's not much anyone can do (although even in that scenario depending on when and where the tragic event happens you might still have a puncher's chance), but short of that it is very helpful to have a support network designed specifically to do all that is possible to make your passage a safe and enjoyable one.
One last point about rallies and then I'll stop. Simply figuring out everything that you need to figure out in order to make a passage is the better part of a full time job. A rally spoon feeds you everything you need to do and know in order to make the passage. Take the lists, do it all, and you at least will have comfort that you've prepared yourself and the boat without forgetting something important ("what, I actually needed to get a decal ahead of time in order to re-enter the U.S. without having to take my boat to a customs office?"). That's a real value too.
Someone mentioned signing on with John and Amanda Neale to get passage experience. Another option, perhaps less expensive (I'm not entirely sure), is going for a trip with John Kretschmer. John's a great guy with tremendous experience, and he does some very cool trips (including an around-the-world gig in about 30 days). His website is www.yayablues.com
(I have no professional relationship with him, so have no fear that I'm a shill or anything).
Good luck with your search for a rally on the west coast. You might check with the folks at Lats & Atts (www.seafaring.com)
, as they seem to have their finger on the pulse of all things related to west coast sailing, including the location of all the best sailing events and parties!
If you want to talk about it further, feel free to email, pm or call me (all contact information is on our website).