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West Bay Road
Seven Mile Beach, Grand Cayman
Tel: 345-947-2782

Named after a legendary Cayman sailing ship, this colorful spot has the same owners as Chicken! Chicken! but it’s a couple of steps up in price, with far more variety and atmosphere. It’s steps away from its sibling and across from the Marriott. The food is a tasty mix of Caribbean and Mediterranean—light fare like roti and jerk-pork sandwiches along with seafood (shrimp brochettes) and interesting pizzas (pesto, pine nuts and eggplant!) and pastas (firecracker bow ties, with veggies, pine nuts, olives, basil, feta and a healthy dollop of Scotch-bonnet peppers). You can watch it all being whipped up in the open kitchen.

Northwest Point Road
West Bay, Grand Cayman
Tel: 345-945-5217

One of Grand Cayman’s dining old-timers—founded in another location, Seven Mile Beach, in 1981—has in the past couple of years totally retooled. Back in 1995 its new owners moved it up to the rocky shore across from Boatswain’s Beach (see Play) in West Bay. Now they have Salzburg-born chef Bernhard Prahauser in the kitchen producing such delicacies as green-plantain-crusted grouper and coconut-shrimp-topped pink snapper in a red curry sauce. And, of course, plenty of conch: fritters, ceviche, two types of chowder and the eponymous cracked. The decor is a handsome mix of classic and modern, and waterside patio dining under the stars is a surefire romance kindler. The Sunday brunch always draws raves.

648 South Church St.
George Town, Grand Cayman
Tel: 345-949-9333

They’re not kidding when they say "grand"—or, for that matter, "old." This gracious seaside manse at the Petra coconut plantation celebrates the big 100 in 2008. Since being turned into a restaurant in 1969, it has become the islands’ top spot for banquets and other special events, whether in the old-fashioned white interior or out on the covered and open decks. The menu deftly mixes the classic (Angus tenderloin in peppercorn sauce) and the nouvelle (ginger-sesame yellowfin with a potato crust). For something you can really write home about, try the green turtle steak scaloppini in a tomato–white wine sauce with herbs, onions and peppers. The wine list is a winner too and has an interesting quirk: You may never again come across so many Austrian vintages.

245 North Church St.
George Town, Grand Cayman
Tel: 345-949-2736

Here’s another Cayman classic with a great wine bar and an expansive wine list also strong on Austria (thanks to manager Gunter Gosch). The Lobster Pot is a bit less elaborate than the Grand Old House but dates back further as a restaurant. This spot on the north George Town waterfront has been a local favorite since it was launched in 1965. Owned since 1981 by the Cumber family, it has a homey ambience, picture windows with expansive sea views and very tasty surf and turf. Yes, lobster is the specialty—whole, tail with drawn butter, with linguine or combined with seagoing colleagues (as in the Cayman trio—broiled lobster tail with grilled mahimahi and garlic shrimp). But the conch, the catch of the day and the steaks are also excellent bets.

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