While not an expert, I've done the 'bash' two times in my own boat and agree with IRG's assessment. Picking the most opportune time of year to do this trip and then picking a good weather
window to leave are key. There is a great deal written on the subject. Jim Elfers, who has done a great number of deliveries from Cabo north, has written a book "The Baja
Bash", which contains valuable information. The best time of year to leave, based on his experience, is early summer (July is the most benign) or late fall (November/December).
Both of the bashes I did were in summer ('09 in July; '15 in June). Since the predominate weather
along the Pacific coast of North America is out of the NW, you can expect to be motor-sailing on much of the bash north. For the trip up the outside of the Baja
Peninsula, you'll want your engine
to be in top running condition and have the range to comfortably reach Bahia
Tortugas (~350nm) for refueling. There is another option of fueling in Bahia
de Magdalena, but it requires a trip along the circuitous channel into the port at San Carlos
Sailing from San Carlos
to Cabo San Lucas will be a relative milk run with many opportunities to explore and relax on your way south. Once in Cabo San Lucas, you want to look for your weather window to round Cabo Falso and make your first leg up to Bahia Magdalena (or Bahia Santa Maria, a beautiful anchorage about 18nm further to the north). While fuel
may be had using jerry jugs through difficult surf landings in several coastal developments, taking fuel
directly on board north of the Sea of Cortez
may be done in Mag Bay (Puerto San Carlos), Turtle Bay, Cedros Island and Ensenada.
Once beyond Bahia Magdalena, the longest unprotected stretch of you passage
will be crossing Bahia Vizcaino between Cedros Island mainland Baja. Otherwise, there are several points and bites offering anchorage and shelter from the predominate NW weather. Again, Jim Elfers book gives the most complete description of what to expect and how to plan for your bash. You're biggest surprise heading up the Pacific side of Baja will be how cold and damp it can be, even in the summer! Good luck and enjoy the journey.