Re: San Diego
San Diego has some of the most temperate weather in the world. It hardly ever rains and there's a lot to do. Downtown area and Seaport Village are great. Horton Plaza (also downtown) is a cool mall, very eclectic. Jim Croce's restaurant is a few blocks from Horton. Make sure you visit La Jolla for the best views of the ocean and the seals. Coronado is great too. Its across a scenic bay and bridge directly across from the downtown area. There are ferries you can take around. The Hotel Del Coronado is excellent to visit even if its just the lobby. A rather pricey hotel but plenty of atmosphere and its a historic landmark.
Since you're lifeguarding you may need a wet suit since California ocean water tends to run cold even in the summer.
If I was going to a casino I'd probably prefer Sycuan Indian Casino (east of Rancho San Diego). It's more out of the way but not as crowded as Barona or Viejas. I'm not sure about the poker action at any of them though all 3 probably have it.
You probably want to surf city of San Diego sites to see how to avoid any fire areas from the recent fires. San Diego also has terrible traffic during rush hour. It's the 5th most populous U.S. city.
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