Travelocity is pretty reputable. I prefer to go directly to the airline and hotel, but that's mainly because I travel a ton and want the points
I've never bought travel insurance and I've never needed it.
The Caymans are beautiful. The Ritz's pool looks kinda like a Mickeyhead if you're interested.

The Caymans are beautiful. The Ritz's pool looks kinda like a Mickeyhead if you're interested.