There is no part of George Town that I would feel in the least bit unsafe to drive through. The island is, in general, one of the safest around. If you discount Sheddon, Crewe and Eastern Ave as ways you can use then you rapidly get quite limited.
The restaurant selection on the island is up there with the best, IMO - prices are similar to a big city restaurant prices. There are menus with prices and a map at
Grand Cayman Restaurants Guide for Cayman Islands Restaurants but some names for higher end dining would be The Brasserie, Grand Old House, Luca, Blue, Osetra Bay (those two are really high-end, with prices to match!), and Agua.
For more mid-range there are many - some of my faves are Morgan's, Catch, Ragazzi, Tiki Beach (dinner - the lunch there is quite different), Cracked Conch, Blue Cilantro.
You have the various restaurants in Camana Bay - Brooklyn pasta and pizza (not what I thought it would be!), Karoo, Abacus, and the gelato shop for dessert (not to miss, that one!)
For dinner outings you have the catamaran ride over to the Rum Point Club - a really nice experience without breaking the bank. There are also all-you-can eat BBQs at Kabo (boat ride over the sound), Macabuca (on Monday's).
Then more casual you have Craft (a gastropub), Chicken! Chicken!, Welly's Cool Spot, Macabuca, plus several jerk stands.
But if you want over-the-top, you need to do a Sunday Brunch on the island - in my experience, the Ritz one is the top of the line, and also the most expensive. The one at Luca is really good, too.
My only negative would be Calypso Grill - I know that it's the fave of a lot of folks, and it was cool when I first went there 15 years ago, but it's stayed the same while others have improved and I wouldn't rate it any more - cramped tables, and unimaginative sides with the dishes. There are far better waterfront options, imo.
