We used to take the Norweigan Crown from NYC to Bermuda. It would stop in Hamilton and St. Georges. It was a pretty small ship so it could fit in the channel leading to St. Georges where today's ships are too big to fit in there. I think the ships now go to an area called Wharfside or Dockside. Hamilton is being widened to let the bigger ships in, as I understand it, so it will be a while before the mega ships start to go back there.
Anyway, Bermuda is not a tropical climate so going in May is hit or miss. Sometimes, we would hit great weather and other times all we hit was rain -ugh. The water temp was also too cold for me! You won't find island or Hawaii water temps in Bermuda!
Its a beautiful place though! The people are friendly and crime is almost nonexistant. Although, with this economy, I don't know if that is true anymore...
Hamilton is the place to shop. Front Street has a ton of shops to choose from, although as of a year ago, many shops had closed because of the economy. St Georges, too, has felt the economic crisis in that a ton of shops had closed. There are great restaurants in both places, though. Also, pretty good shopping in the Wharside or Dockside I had mentioned.
Good Luck!