Multi-day flight plan?

I originally posted this in the wrong forum and was directed here. My apology for that.

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I'm curious to know if I can file one flight plan that covers multiple stops and even days?

For instance, say I want to fly from San Diego Intl to San Francisco Intl with stops in Los Angeles and San Luis Obispo. I want to land in Los Angeles and have lunch then on to San Luis Obispo where I'll spend the night. Then the final leg from San Luis Obispo to San Francisco.

Can one flight plan be filed to cover the entire trip or would I need to file three separate plans - one for each leg? Or two plans - one for each day?

Flight plans serve two purposes, for IFR clearances and to trigger searches if you don't arrive. You didn't specify VFR or IFR (they're way different), and while I can't give you a definitive answer, I'm not aware of this being done.

For VFR flight plans, you'd completely defeat the purpose of the flight plan, since ATC isn't normally involved and the only time anyone looks at it is if you don't arrive AND close your flight plan within 30 minutes of your ETA, to get get a search started. So I doubt that would be allowed.

For IFR flight plans, the primary purpose is to fit into the ATC system and to maintain traffic separation, though the secondary purpose is the same as that for VFR. I again don't see this being allowed, since you'd not have any search for you if you failed to arrive (unless you disappeared while talking to ATC, not always the case), and you couldn't close the flight plan if it were to continue the following day.

One thing that IS done, by the airlines and perhaps certain other scheduled operations, is to have flight plans on file that are activated each day as the flight is ready to start, but these are closed each day, too.

The Aeronautical Information Manual (AIM) discusses all kinds of things about flight plans, both IFR, VFR, and combination, starting on page 5-1-7. The AIM has a huge amount of other information you may wish to know in addition to that, and while it technically isn't a regulation in and of itself, it does define best practices and it often summarizes, and even expands explanations of, actual regulations, so the effect is usually just as if it were a regulation. It covers ATC operations, radio communications (a glossary too), and many other facets of aviation.

On this FAA page you can see links to all sorts of manuals and handbooks that will probably answer more than you want to know about aviation.