Which hotel should a middle-aged couple chose for a long weekend in May? Can we walk to restaurants from the Hilton?

There's more to walk to from the Hilton, but I think Sand Key is a nicer, quieter beach. Clearwater beach is VERY junky and touristy.

We stayed at the Sheraton Sand Key and found it to be a convenient location for dining and a nice beach.

I agree that the Sheraton is probably nicer but not as convenient. We stayed at the Hilton last March. They were in the middle of renovations, so it's hard to say what it would look like now, but it was certainly nothing special. Several restaurants/shops to walk to, but the Hilton is pretty much in the rotary as you come into Clearwater, so if you are looking for something on the peaceful side, then Sheraton is definitely the way to go.

We stayed at the Hilton Clearwater last week. The street is a little noisey around the rotary, but the beach is extremely nice. White, wide, pleasant. Wonderful beach views from the hotel restaraunt. Several great restaraunts within 3 easy blocks walk. We'd recommend the Palm Cove and any of the three Frenchy's. We enjoyed the local casual atmosphere at them all. By the way, make sure you visit Tarpon Springs. Very authentic Greek cafes. Shopping is a little touristy, but a very unique place to visit.