Would it be worth flying to Cabo San Lucas from the east coast?
Cabo can be amazing... HOWEVER, it's very fickle and heavily swell dependent. I spent a couple of weeks there during a good swell window and drove hundreds of miles to all of the well-known and many unknown points and beach-breaks. The swell go up to about 8 feet, but the south facers never really panned out, closing out everywhere for miles. The Pacific side was more fun (likely the angle of the swell). There's a little point called Cerritos that is super crowded when it's small, but strangely empties out when the size rolls in.
In short, I won't be rushing to go back. There are better options for surf travel from the east coast than rolling the dice on Cabo (unless you're into clubbing, hookers, bad weed... which Cabo has in spades).
Winter has the north swell and that means east facing Pacific coast. Like PhiloSurfer said Cerretos is a really fun right and there are other breaks in that area about 1 hour drive from Cabo. I went up to the town of Todos Santos(not the island) and that was a surf flop but cool town for lunch, arts and crafts shopping, and has a surf shop. If a little later in the year with southern hemi swell the east cape (south facing east of Cabo) can get really good with an insane amount of small points that light up and go unridden (check out Google maps). I stayed in San Jose del Cabo that is about 15 minutes east of Cabo, closer to the airport, smaller, and much nicer than Cabo. You can find very reasonable condos right on the beach, walking distance to Zippers, and you can start your east cape search from there.
Last edited by MellowMonday; Mar 3, 2013 at 04:54 PM.