Half Moon Bay
Hi Jeremy,
Parking at the airport is easy, there is transient parking at the southeast end of the runway, and from there a nice walking path into the village of Princeton-by-the-Sea, which is the fishing harbor area of Half Moon Bay. I don't know if they even charge for transient parking there - I've never stayed over night.
There is one Hotel there, the Oceano Hotel and Spa. It looks pretty up-scale. There is also a bed&breakfast-style inn called The Inn at Mavericks.
There are a handful of restaurants there in Princeton, the two I like best are the Half Moon Bay Brewing Company, and Mezza Luna, which is a very nice Italian restarante.
If you would like to take a cab (or perhaps the Hotel has a shuttle?) into the city of Half Moon Bay, there are a few other nice restaurants - my favorite is Pasta Moon.
ATC is easy to work with coming south. If you would like, you can actually stay clear of the SFO class-B airspace and not even talk to anyone - but it is surely advisable to work with NorCal Approach. The flight south passing west of the Golden Gate Bridge, and south just along the coast to HAF is spectacular.
If you are VFR-only, the one complication may be the normal coastal fog. It varies in height and extent from day to day. Often the coast is clear in the middle of the afternoon, other times, the coast is shrouded in heavy stratus fog to the ground. Most typical pattern probably is for the fog cloud base to be around 1000-1500 ft, so you can sneak along the coast under it.
The weather pattern to look for to ensure a clear coastline is a high-pressure ridge extending into southeastern Oregon and Idaho. This produces an off-shore flow that gives us warm temps and pushes the marine fog far out to sea.
If you would like a local synopsis/assessment of the weather and strategic suggestions for getting in under the fog, ping me with a PM a day or so before you depart and I'll take a look.
Hope that helps,
Steve.