Grand Cayman, like Oakville, has a British Heritage, and is still a British colony (if only, eh Oakville?). It is not a colourful town – lots of beige and off-white - much like Oakville, and unlike most of the rest of the Caribbean. You can shop for all kinds of useless items in the downtown shopping district, just like you can in Oakville. You will also spend too much eating in restaurants there, again, like Oakville. Except for the palm trees, the middle-class neighbourhoods have a very Oakville-like feel to them. Most people drive SUVs in Grand Cayman, except for those in the Ferraris and Porches. The Lincoln Navigator is a favourite.
I must say, though, that the beaches are much nicer than Oakville's.
One difference between George Town and Oakville is the number of banks. George Town has hundreds, whereas Oakville has only dozens. Also, I've heard you need a minimum of $100,000 to open an account at most Cayman Islands banks.
Although Grand Cayman is British, you rarely hear a British accent outside the Scottish bakery or the place that serves afternoon tea to tourists. Or maybe the pub. Most Caymanites talk American, and they drive on the American side of the road.
When I visit an island, or a country, I like to tune in to its radio stations. It helps give you a flavour of the daily life in a place. That's one reason why I always travel with a radio.
One of the few radio stations in George Town is K-109.9, Kayman Kountry! A country music station for the oil-rich Texans who do their banking there. Not very British, that.
To be fair, I won't really say much more about Grand Cayman. It's a tendering port, meaning that the ship moors offshore and we must take tenders to and from George Town. And that means that we have to wait until after the morning rush to leave, and return at least an hour before the last tender (the afternoon rush). That cuts down shore time a lot. For that reason I tend not to venture over unless I have something specific planned.
Also, George Town is very expensive (like Oakville). Nobody I know likes spending the money they ask for food or drink there ($5/beer when it can be as low as $1/beer in other Caribbean ports). And you will probably want to take a cab to the beach, as it is some distance from downtown. You could bicycle there, except they don't like you to take a bicycle on the tender.
On the other hand, I've talked to several people, mostly divers*, who do like to get over there. I hear the diving is excellent. Also, there are some interesting things to do, like swimming with stingrays, or playing with sea turtles, if that's your sort of thing. And, of course, the beaches are perfect for swimming or sunbathing.
Grand Cayman is flat, and even flatter since the hurricane. They're rebuilding quickly, but the damage from the hurricane is extensive and still pretty obvious months later. For several weeks after the hurricane (just after I arrived) the port was closed to ships. It is said that the entire island was under water during and just after the storm.
I can believe it. On this last visit to Grand Cayman I mosied up to the upper decks to get a better view and discovered that I could see the entire island from up there. It is flat. From 14 decks up it looked almost like something that was spilled out over the ocean. Just so much flotsam and jetsam. The trees across the island, at least those that were still standing, were defoliated and brown. It wasn't nearly as green looking as it should be, being a Caribbean paradise and all.
It'll all come back though. It always does.
*Many crew members acquire their diving certification as the course is offered to them, right on the ship, at a deep discount. The cost is $249, and that includes classes, rental of equipment, and several training dives in the ocean. The certification is good for life.
Some crew go on to the second level of certification allowing them to become diving instructors or underwater guides, which can be quite lucrative.
Omar, my cabin-mate, is currently enrolled.
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