Went to Bermuda about 14 years ago and stayed at Ariel Sands, which is owned by actor Michael Douglas. His mom is a native of Bermuda. He happened to be there and we spent about 20 minutes talking. His dad (Kirk Douglas) grew up in Amsterdam and he still has aunts and cousins around the Albany area. Talking to him was like talking to anyone else you might run into overseas where you just happen to know people in common.
Ariel Sands was really nice. Kind of a small place right on the water. We would definitely go back there. We went in June and the ocean was still cold. Bermuda is not the Caribbean, so don't think the water temp is going to be 80. More like 60 in June.
We took buses everywhere. Very easy to get around and you get to engage with the "natives". BTW, everyone we met there was very nice. Very British and more formal than other islands, but it was a very nice atmosphere. However, if you are going there to party, I would choose another spot. From what I remember it is very quiet and romantic.
If you are going late May and want to lay on the beach, go to bars or clubs and maybe a casino, I could tell you about at least 10 other places that I have been that would be much better. If you just want to hangout with your wife, do a little sightseeing, have dinner and a lot of quiet time, Bermuda is perfect.