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Morritts Restaurant (David's) - On the northeast tip of the island, Morritts timeshare resort has a couple of restaurants, the largest being "David's". Many people eat there especially for breakfast on this side of the island. There is some nightly entertainment there, but call to be certain when/what. Lammie's show is pretty funny.
Royal Reef Restaurant (Castro's) - In addition to the inside restaurant of this time-share resort (next to Morritts), they have a great beach bar called Castro's. It is oceanfront and serves great drinks, light fare and is a gathering place for tourists in the east end. No reservation necessary. The inside restaurant also serves dinner and they have "The Barefoot Man" sing/perform each Tuesday & Thursday at a dinner show (about $40/person).
Lighthouse Restaurant - The Lighthouse is the best restaurant east of Georgetown. This is a 4 star restaurant with uniformed wait-staff, an excellent wine list and superb menu. Also Caribbean and Italian, the Lighthouse has a wonderful new bar/lounge and an oceanfront screened dining porch. You can listen to the waves break on the rocks below while enjoying some of the finest food on the island. For a special dinner, "Captain G" (Giuseppe) also has his "port room" which is an air conditioned (wine cellar themed) private dining room with a large round table that can seat 10-16 people. A dinner in the Captain's port room is a true memory, and you would need reservations for this experience. I would always suggest reservations for the Lighthouse to be certain that a table is available. Located in Breakers - which is on the way to town. It is just west of the main North/South road bisecting the island.
Over The Edge - On the way to Rum Point on Northside, just after the awkward left-hand turn in Old Man Bay on the northcoast; there is a small green (oceanfront) restaurant called "Over the Edge". It is part bar and part restaurant, and has great seating over the water on their dock, which is a great place for kids for dinner. The fish, stingrays and sometimes octopus swim right up at dinner time, attracted by large lights the french owner shines in the water. No reservations required for this casual place, less expensive too. They also cook breakfast, lunch and dinner.
Driftwood Village Sports Bar - I include this Sports Bar because they have a Great Sunday afternoon BBQ with ribs, chicken and shrimp. 3-7PM on Sundays only. The driftwood is on the way to Rum Point on the oceanside. Great watering hole with a pool table and 6 satellite tv's. The food is from Durty Reid's restaurant which is in Red Bay near Hurleys grocery store, if you gets hungry for their ribs on the way to town one day.
Rum Point Club - This beach club is the #1 place to hang during the day (except Sundays-too crowded). They have a great outdoor grill with waiters and picnic tables, lounge chaises and hammocks. Super bar as well as a gift-shop & clean showers/bathrooms. The larger formal restaurant on the property won't reopen until the Hyatt (who runs the club) has renovated the complete hotel on 7MB and resumed ferry service from the hotel to the Rum Point Club pier. That will probably occur in 2007, so enjoy the less crowded situation during 2006 while you can. Snorkel & Dive boats leave from their pier, as well as private charters.
Kaibo Yacht Club - Near Rum Point, the Kaibo Yacht club & Marina is a great venue for a casual meal and for entertaining the kids. The quiet cove that the marina is located in has a small swimming dock and the dock is a great place to see fish swim by. The food has a Cajun flair, as Jerry (the chef) is from New Orleans. The Kaibo also celebrates Mardi Gras each Spring (specifically Ash Wednesday) with a huge beach party. The (more formal) restaurant upstairs may not open again until next year, but the food downstairs is awesome and the bar has a few satellite TVs as well as some of the coldest beer on the island (they make their own ice for the beer coolers). The Kaibo is also the dock where you catch the Red Sail Catamaran for stingray city and is a great place to have a lunch afterwards. Volleyball net, dock and lounge chaises on premises. The manager (Daniel) is a great host.
Various Local Jerk Chicken/Pork Stands: There are a number of roadside vendors of Jerk Chicken, Pork, Fish, etc. around the island. I like the two in Boddentown the best, Chester Watler's Fish Fry and Wood's Grilled Chicken. There are a few others scattered in the East End..all are fine and are inspected by the government. I would stay away from people serving food out of their cars. The best rotisserie chicken on the island is at Chicken! Chicken! in a pink shopping strip mall on 7 Mile Beach just south of the Hyatt and north of Wendy's. Great place to eat on the day of departure (they open at 11AM).
Bamboo (in the Hyatt) - This is a great (eclectic) sushi bar with awesome music & food. After dinner you can walk on their beach or sit down around their pool on a padded lounge chaise. Their food ranks in the top 5 restaurants for 7MB for me. The Hyatt also has some cute shops for window-shopping afterward too. View of ocean/pool. Great bar next door at Hemmingway's too.
Calypso Grill - Is my absolute favorite restaurant on the whole island. It is a long trip from the East End, but worth it actually. Calypso Grill, Cayman Islands restaurantIt is built on a dock in Morgan's Harbour at the top of 7 Mile beach. The menu is very large and they have just about anything you could possibly want.
Castaways Grill - Located a little closer to you in Grand Harbour (Right behind Hurleys Grocery Store) is a new restaurant that makes fresh pasta meals and oven-fired pizzas, as well as other elegant fare. There is an outdoor covered patio for al fresco dining, as well as an adjacent ("Davey Jones Locker"), sports bar/restaurant (best on the island) for the big game. It is closer by, and if you are running to the grocery or liquor store for something anyway, this is a great choice. Also on the property is the world famous "Black Pearl" skateboard park and a wave machine for surfing!