My Better Half has been several times to visit family, and feels totally comfortable and safe. Now, keep in mind that he is not the photographer in this household, so I sent him off with a Canon G10 set on Full Idiot Mode, and I was prepared to handle all the post processing upon his return. He came back from his first trip with hundreds of photos that he took through the car window, and they all had a nice reflection of his mint green shirt in them. So I gently explained to him why this was a problem and he took my advice to heart. On his next trip, he remembered what we talked about, and rolled down the car window. This trip produced a whole slew of self portraits like this one.
He did manage to get out of the car at certain times, and with a little effort in post processing, there were some real gems.
And my personal favorite:
So, if you're uncomfortable with the idea of lugging a lot of expensive gear, don't be afraid of a quality point & shoot camera. It can and will get the job done.
Also, to echo what Clive said, get out of the resort. Get out of the city too. There is much to see throughout the country.
