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It takes a day and a half of driving just to get to SD if you make minimal stops just to eat/gas and spend the night somewhere. From there I think it's like 700 miles of road to get to Cabo, someone on the San Diego or California forum should be able to give you an idea on how long it takes. At any rate it is going to require a LOT of driving. You could go south at Tucson and head to Sonora and take your car on the ferry over to Baja which may cut off some of your driving but it costs several hundred $$ and you'd miss much of the spectacular desert scenery of Baja (I'm assuming that's why you want to drive instead of fly)
Keep us posted, it's one of those dream drives I've wanted to do for years now. The closest I've been is San Carlos Sonora. Like Sonora, you don't need to get a Mexican car import permit to go to Cabo, though you'll want Mexican insurance (given all the driving in remote Baja it'd be nice to have one with a good towing/roadside policy - just in case). You still need the standard tourist card
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Driving From: Austin to Cabo San Lucas
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