A copy-paste from an earlier post:
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Some topside attractions that proved popular with visiting friends and family:
Pedro St. James castle
A renovated old 'plantation house'. A nice insight into the past of the island. They have a sort of interactive show illustrating the history of the island. Also a display of nice old photographs of the history of the island.
Welcome to Pedro St. James
Queen Elizabeth II Botanic Park
Botanical gardens in quite a nice setting. Showcasing some typical Cayman flora and fauna, and also some from around the world. Also breeding ground for the Blue Iguana, only to be find on Caymans as I understand.
Queen Elizabeth II Royal Botanic Park
You can get one combined ticket for both. Each is probably about 1,5 hr visit and makes for a nice change from heading to the beach.
Kaibo
Great 'yacht club' style place on the beach just a few minuted further then Rum Point. Every of my guests who I showed both opted to go to Kaibo and skip way too touristy Rum Point, and it ended up being one of their favorite places.
KAIBO- Restaurant, Beach Bar, Marina, Cayman Islands
Unfortunately Cayman hasn't got too many seaside restaurants/bars, as most of the seaside is used by the resorts and condo complexes.
Some of my favorites:
Rackhams in Georgetown. Popular with both visitors and locals, especially on weekend nights.
Waterfront Bar & Grill Dining Restaurant | Cayman Island
Al Fresco in West Bay. Great terrace right on the beach, but affordable prices. Especially check the specials advertised inside behind the bar. Some BBQ ribs with rice and veggies for 7 CI, on a terrace on the beach is a steal for Cayman standards.
Alfresco - Flava Cayman
Cocolobba
A bit of sneaky choice as I tried to avoid hotel bars, this is the seaside bar/grill at the very upscale Kimpton. However the food, service and location are very good, and prices quite reasonable seeing the location and that it is the Kimpton. Proved very popular with visiting friends and family.
Kimpton Seafire Resort and Spa
Macabuca
My favorite bar on the island, and were I usually end up (well it is also close to home!). Great seaside location, and a nice little cove for some swimming, or a snorkel or dive. Best sunsets on the island. Monday nights they have a great 'all you can eat' BBQ and all-night happy hour.
Macabuca | Cracked Conch-Macabuca - Restaurant Bar and Grill - Grand Cayman
Some mentions for my favorite restaurants.
Catch
Not the most budget place, but amazing food and I would say good value for the quality you get. Nice dockside location. Can be windy in winter months, so worthwhile to book ahead and request a table on the terrace behind the screens. If you dive with Divetech you can get a discount voucher, although I think you'll be still happy if you were paying full rate for this great food!
Welcome
Liberty
In a residential area in West Bay. A kind of 'local' restaurant also doing great Asian food. Highlight is the freshly BBQ'ed Jerk chicken and pork on Fri/Sat. Best on the island!
Liberty's Restaurant, Grand Cayman - Restaurant Reviews, Phone Number & Photos - TripAdvisor
Gelato
Ice cream to die for. Addictive, you'll find yourself 'dropping by' if you're anywhere near their stores. Locations in Georgetown and Camana Bay.
Gelato & Co | Cremeria Italiana, Grand Cayman
A place I did't specifically mention, but which is always very popular, is Calico Jack. Very lively beach bar, and probably the most 'party bar' on the island. I seem to have grown too old to enjoy that scene...