Your sig says "MN" are you in Montana? If so, I can vouch for Oahu if you can find good lodging at $250. Kaneohe has amazing flats but few fish, I saw more on the residential south side near the naval base and the biggest, in fact unimaginably big bonefish on the southwest lagoons of Ko Olina but it is a patrolled no fishing zone. I did not investigate the flats around the Marine base at Kaneohe. I'm sure you can find places around Waikiki as well, and you can hire a local guide to show you the proven flats. Flights from the northwest are easy.
For us east-coasters the Bahamas have a lot to offer - I liked Harbor Island as a his/hers destination but there are many options depending on how picky your lady is
The beaches are beautiful beyond description in these archipelagos and there are bones lurking pretty much all over. Turks and Caicos now you're talking... but again more of an east coast destination.