If you're going to Bermuda (I've been going there for over 3 decades) here's a few hints that may help things.
The island is only 22 sq. miles, so you can't really get lost there. Lots of guests rent mopeds, which is a neat way to get around the island--be warned, however, that THEY DRIVE ON THE LEFT SIDE OF THE ROAD, and for those who may be intimidated by that, don't worry--cab or bus is always available to get from A to B.
The So. Shore beaches are the best, especially Horseshoe. You have changing rooms there which is nice, and the water is just great. Going to Gibbs Hill Lighthouse is a must--a bit of a cabride, but if the weather is nice, walking up the lighthouse is worth the visit. Also, there's a wonderful English style pub there that has breakfast and lunch, and is fun and clean.
Taking the ferry over to Dockyards is fun, and there's lots to do there. There are several places to eat there (the Frog and Onion is one of my favorites) and there are several art displays in the general shopping area. Walk over to the Quartermaster's House, the one on the hill--there's an admissions charge to the museum and house, but it's worth it.
Bermudians are very hospitible, and will gladly answer any questions you have. Drink and 'dark and stormy' (ginger beer and dark Black Seal run) and watch the world go by at a put--life is awfully good from that vantage point!!
Enjoy the island, and I'd be interested to hear your views on the destination.