Each fall, for the past 16 years, a group of more than 150 boats do the Baja Haha cruisers rally from San Diego to Cabo San Lucas.
There are benefits to participating. It forces us to set a date, since the rally is happening with or without us. We would get meet a lot of other cruisers who we'd undoubtedly run into again and keep contact with - especially good as we'll be cruising with a teen, and there always seem to be other teenagers+kids in the rally. As first-time cruisers to Mexico, it makes a lot of sense to go with other boats that have done the trip before. And it just plain looks like a ton of fun, with beach BBQs, potlucks, and so on.
But there are negatives as well. The trip happens on their schedule - though it's loose as organized rallys go, if you find a cool spot, or want to go on a diversion, you can't really spend a few days exploring and relaxing. There's a certain party element to the Haha. Opinion on the latter depends largely on who you talk to in terms of how family friendly it is. We wouldn't otherwise even bother with Cabo, and would just continue around towards La Paz. Finally, 150+ boats is a lot of fiberglass, masts, and crew all in the same place, and we would probably try to time our trip through a week or two before the Haha anyway.
So what are the alternatives? There's not much of anything along the Pacific Coast of Baja. Since we don't want to do this 750nm trek alone, that leaves us with finding a group of buddy boats. Naturally, this poses it's own set of positives, negatives, and unknowns.
At this point we have not made any decision one way or the other, but are strongly leaning towards going with the Haha. However, if anyone reading this is planning on heading to the Sea of Cortez around the mid-October timeframe and looking for buddy boats, please get in contact with us. I'll toss this query out on a couple of mailing lists and boards as well.
Additionally, if anyone has specific thoughts and experiences to share about the Baja Haha, please don't hesitate to pass them along. We appreciate hearing what others have to say on this topic.