I made that same flight as an Angel Flight just 3 weeks ago.

I flew IFR - and needed it because there was a solid marine layer over all
of Southern California.

I actually picked up my passenger at Watsonville (KWVI) and the route I
filed was as follows: (This will make more sense if you have a Low Enroute
Chart to look at)

SNS.V25.VTU.V27.MZB.V66.BARET

I know the V66 to BARET leg looks weird - but that is what it takes to get
to the Initial Approach Fix for the ILS approach into MYF. I file it so ATC
knows where I'm going to go if I lose my radios.

Actually, just after San Marcus VOR (RZS) we were cleared direct SXC (Santa
Calalina). This actually took us a loooong way out to sea and in hindsight I
would have picked a route closer to land. Not long after SXC we started
getting vectors that brought us in on the north side of MYF for an ILS
approach.

Next time I will file
VINCO.V107.PXN.V113.ROM.V485.VTU.V299.LAX.V23.MZB. V66.BARET

If you are flying IFR out of RHV going south then VINCO.V107 is what you
will almost always get (no matter what you file)

On the way back we got a lot of re-routes from ATC. One very nice lady
working the departure from San Diego suggested that I should have filed the
following route to avoid all the trouble:

MZB.V23.LAX.V299.VTU.V485.GILRO

I would rather fly IFR rather than deal with all the complex airspace around
So Cal. The other way is fly above 10,000 over LA and be careful on the
approach into MYF.

Lastly, I try to fly high, 8000 is uaually the minimm altitude I'll file for
and typically I try to be at 10, 000 or 11,000. The highest MEA on the route
I suggested is 9000 (around FLW VOR). This is in a C182.

We left at WVI at 4pm, had dinner in MYF (the Mexican food in the terminal
restaurant is good) and landed back in RHV just before midnight. I brought a
very capable co-pilot with me to keep me awake and share the load - a very
good idea on a long flight like this.

-Brenor
N182AK