Caribbean Charlie’s - On the way to Rum Point, across from the post office, there is a left turn to “Hutlands”. You wind through a neighborhood, and take your (I think) second left to his house (small sign). Charlie Ebanks makes handcrafted whimsical birdhouses and furniture, etc. It is all handmade, painted, etc, it is not cheap, but if you are looking for something unique to take back from the island that is local to the northside…you may find it there. It is worth a look, either way (if anyone in your group is a giftshop nut).
Lighthouse Restaurant - Absolutely one of the best restaurants in the east of the island. Make reservations for the screened porch. The food and atmosphere are fantastic. Save room for their signature dessert, Beignettes! Order only one plate for every 4-5 people! It is large, but this is the best advice I will give you during your visit. If you eat somewhere else in town, and are driving back to Northside, and only get to stop for Beignettes and coffee, do it…also, they sell the little lighthouse coffeepot/teapots out front, a great (cheap) memento.
Atlantis Submarine Trip - In Georgetown, near the main harbor, is the Atlantis shop on the water. They take you out (on a boat) to their submarine docking station just offshore. For about $70.00 (the cost of a two-tank dive) you get to go in a state-of-the-art submarine down to about 100 feet. They have a truly professional crew of Australian/Canadian/Americans that operate these around the world. Very safe tour. If your group won’t do it…there is the Nautilus semi-submersible just up the street. It, however, never submerges. It is like the Disneyland submarine, but larger, with drink service. Whichever you choose, the evening tours are the best, as the predators/nocturnals start to come out (Tarpon, barracuda, sharks, squid, lobster, and octopus).
Go to Hell? - North of 7 Mile Beach, in West Bay, is a stark, limestone/stalagmite field that the locals have named “Hell” (Complete with t-shirts, etc) Don’t waste your time, unless your kids are screaming to go (which they won’t). The only thing redeeming, is that it is close to “Ristorante Papagallo”, which is a very nice, (Polynesian Architecture) restaurant, but it is so far away from everything, especially Cayman Sands, that we have never been!
Roland’s Garden – Roland is a former chef who runs an outdoor (campy) "restaurant" at his house in the Cottage District, on the South coast of the island. Not well-marked, but you will see about 10 tables in the trees behind an anchor chain fence, about 1.5 miles East of the Frank Sound road intersection at the bottom of the island. You arrive at his place, he tells you about dinner tonight, if it sounds good to you, you stay and eat (bring your own beer/wine in a cooler), after dinner you pay him what you feel the meal was worth. No bill. It sounds hokey, but true. I have eaten there many times. His food is very good.
Sunset House - South of 7MB is Georgetown. If you go straight south through town (along the water), Sunset House Hotel is on your right. If you see the oil storage tanks, you’ve gone too far. Pull all the way down to the parking lot behind the hotel. There is a great bar/snack restaurant, and Cathy Church’s photo shop under the hotel. In addition, it is a great place for a shore dive or snorkeling with the kids. This place has a swim ladder to help get into/out of the water. Also has a nice restaurant (Sea Harvest-air-conditioned) if it is too hot to sit outside. You can watch the Atlantis shuttle go out to the rendezvous point, or dive boats come in. Best outdoor bar on the island (Thatched roof).
Smith Cove - Just south of Sunset House (1 mile) in Georgetown is a small public beach cove that many people on the Island consider the best shore snorkeling on the island. Great for kids, as they can walk straight into the water. If the winds & waves are strong on the North/East of the island, Smith Cove is a good daytrip for the waves are sure to be calmer.
Golf - I would leave my sticks at home. The only nice course is the Links at Safehaven, just north of 7MB. It is a well-maintained, 6,000 yd.+ course that is close to the Hyatt complex/resort. It is not cheap, and a trek to get to, unless you take the Rum Point Ferry, and then take a cab. For New Yorkers, it would be like a regular day of golfing (the commute out to Long Island).
Charter a Fishing Boat - Whether you want to go offshore for a full/half day, or go salt-water fly fishing at Barkers flats (near Morgan’s harbor); fishing in Grand Cayman offers a lot of opportunities. I included a few charter services, but haven’t used any as of yet. A local charter (Jerry Whittaker) takes out guests on his ’33 Blackfin (Au’sum). It has a head, shower, A/C and microwave. Wahoo, Tuna, Barracuda, Snapper, Grouper, Mahi-Mahi can be caught while trolling. His rates are the same as everyone’s on the island, full day deep sea fishing US$800, half day $US450. Bait, sodas, ice provided by Jerry.
Shopping - Downtown Georgetown has a ton of jewelry stores, dress shops, souvenir shops, etc. The Colombian Emerald Shop and the Diamonds in Paradise shops are pretty large. 24K-Mon Jewelers also sells mounted Atocha (and other ships’) coins. I am told the prices are pretty reasonable, especially for emerald and coral items.