I've been there twice on week-long cruises.
Climate wise, the all time record low was 44F and high was only 93F. It is close enough to the gulf stream to keep the temperatures moderate year-round.
The first piece of culture shock is that there are no car rental places, and you cannot drive a car on the island as an outsider. They have a decent bus network, along with ferries between locations. Tourists are encouraged to rent scooters, and they are everywhere. First thing the cruise ships tell everyone before opening their gangways is that broken bones and road rash are common from people who rent the scooters, and they recommend sticking to public transport.
With that said, I did rent a scooter for a day on my first Bermuda trip, having over 100K miles riding experience on motorcycles. This goes straight into the second piece of culture shock...Bermuda is a British territory. Royal Mail, fancier dress, and most importantly driving on the incorrect side of the road. For those not familiar with riding motorcycles, adding that additional twist onto the experience along with narrow roads full of busses and I can see why so many tourists wind up in the hospitals. Sooner or later, the brain will lapse entering a rotary/roundabout/traffic circle backwards, and your vacation ends in the hospital having a pink bus hood ornament removed from your face.
I can't comment on the hotels, since we brought our own so to speak. It isn't the cheapest place to stay/eat.
Did I mention that the place is British? The Royal Mail carriers wear button-up shirts with long, formal Bermuda shorts. At least the last time that I was there (10 years ago), the locals frowned on beach attire if you are not actually on the beach. I'm not a beach person and liked the decorum, but someone used to Caribbean beach resorts may be surprised.
I did go to Horseshoe Beach to see the pink sand. I also rode 7 miles of their rail trail on a rented bicycle. Hamilton (capital) is the center of everything. If you like history, St. Georges is a nice place to stroll around. The Royal Navy Yard on the other end of the island has lots of naval history, but was being converted into a tourist trap last time that I was there because no current cruise ships are small enough to get into Hamilton or St. Georges any more so they all wind up at the Navy Yard dumping off 8,000+ passengers on a slow day.
My suggestion is to make sure that you go to Hamilton and catch the
Harbour Night celebrations with the Gombey Dancers on Wednesdays in season. Being a gear head, I also spent an hour or two roaming through car dealerships looking at all of the British stuff/marques that we can't get. Heck, I didn't realize that my entire first day's photos on my first visit was of all the tiny cars that we don't see in the USA!
My favorite memory of Bermuda was accidentally meeting
Stewart Mott at his estate, and getting a personal tour of his gardens (when I thought that our group of bicycle riders was going to be arrested for trespassing). I might not agree with his political leanings, but the guy was eccentric, interesting, and friendly to spend a few hours with. Sad to hear that he died before my second trip.
Anyway, I'd go back again for a third visit in a heartbeat if I had the chance.....