So I have a friend getting married down in Cabo at the end of September. In planning to go down there, I started to think that it would be a lot more fun to fly into San Diego, rent a car and drive down the Baja Penninsula the week prior. I'd then like to fly back home out of Cabo. I did the Mexico spring break deal in college and think 1-2 nights of that in Cabo would be more than enough surrounding the wedding. The multi-stop flights have actually come in fairly reasonable, but a couple issues need resolving:
Can you rent a car in the US and drop it off in Mexico (I'd like to fly back out of Cabo)?
Is the extra insurance super expensive?
Are there any cheap hotels/hostels along the way; camping? Would it be safe?
Is this worthwhile for the time and $$$, or should I just spend the extra days catching rays and ingesting margaritas in Cabo?
I'm sorry I can't be of help with the important issues... But I would go for the extra days of catching rays and ingesting Margaritas!!!
I would strongly recommend against your plan of driving from San Diego to Cabo San Lucas for a few reasons.
(1) The distance is over 1060 miles--which doesn't sound like much until you realize that over 200 miles of this still isn't even a paved road. And of the other 860 miles, all but 60 of this will be on a one-lane road usually following trucks carrying livestock or in a completely desolate area.
(2) There are no rental car agencies that will allow you to rent in the US and drop off in Cabo unless you are willing to pay an extra $700 or so in drop-off charges. In addition, it will cost you an extra $20 a day for the insurance--and, personally, I'd think I'd buy an extra tire to take along--since if you get a flat, you're space saver tire that's good for 50 miles won't do you any good when it's about 250 miles between cities down in Baja.
(3) There's not much to see in most of this area--the area is basically one giant desert surrounded by water on the two shorelines. If you like seeing cactus or studying the life of lizards, great--but otherwise it's going to be a pretty boring--and long--drive.
(4) To give you an idea of how tough this drive is, year's ago they use to have a race from Tijuana to La Paz. The drivers all had dune buggies or modified race cars--and still nobody could make this drive in less than 3 days--and lots of cars broke down and had to be rescued (in fact, that's probably the most interesting thing you'd see on your trip--all the car hulks still alongside the road from the previous races).
But, if you're up to a real adventure--go for it. My two cents is fly and then get a dune buggy in Cabo to adventure around once you're already in the area--like to drive to La Paz and back, for example.
One thing you could do is to take a day or two to drive from San Diego to Ensenada and back prior to flying down to Cabo. This would be fairly inexpensive, much quicker since the road is great, and would still give you the adventure of getting out of the main tourist areas.
Just a thought.
P.S. If you do take this trip, I've posted on the thread "Sedona, Las Vegas, Grand Canyon, San Diego" on what to see in the northern Baja area.