Up to you country just tell me when your going so I can meet up again haha. Nice spice said it best. Plus you have to go back and see Tonatsi before she leaves.
Back in the 70's before I got married I use to fly from LAX to Acapulco 4 or 5 times a year and stay from 3-7 days. I was such a regular that I got the off season rate at my hotel year round. TJ was flyover country. :)
$500-$600 round trip from Louisville to San Diego? I'm sure you could get cheaper than that by booking 2-3 months in advance, especially if you fly Southwest.
Try Cheapflights.com or Cheapoair.com. I just checked now for the hell of it for Louisville to San Diego at a random date in mid-October and it kicked back $316 on Frontier, $355 on American and a little over $400 on United.
Country. This might sound crazy. But drive to Nashville. It's a 4 hour nonstop flight. Even adding the 3 hour drive, that's still a quicker trip than what you are getting from L-ville.
The problems with the cheaper flights is they don't get me back in time for work the frontier and united don't get me back in time only delta and the cheapists after taxes around 500 with my schedule! As far as nashville that is a good idea but i drive for a livin.i hate to drive when im off plus the 3 hour drive and my work schedule would make it tough. So it is what it is.
It's obvious that OP is infatuated with his time south of the border and that's cool. If I ever make it down there I may end up feeling the same way so what we think doesn't matter. It's your time and your money, do what you want.
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Plus I feel it's nice to change scenery and get away from the same-o same-o from time to time - and it gives you something fun to look forward to.