Grand Cayman dining is casual (even shorts are okay, at least for lunch, but not beachwear and tank tops). More upscale restaurants usually require slacks for dinner. Mosquitoes can be pesky when you dine outdoors, especially at sunset, so plan ahead or ask for repellent. Winter can be chilly enough to warrant a light sweater. You should make reservations at all but the most casual places, particularly during the high season.
Since nearly everything must be imported, prices average about 25% higher than those in a major U.S. city. Many restaurants add a 10%–15% service charge to the bill; be sure to check before leaving a tip (waiters usually receive only a small portion of any included gratuities, so leave something extra at your discretion for good service). Alcohol can send your meal tab skyrocketing. Buy liquor duty-free, either at the airport before your flight to the Cayman Islands or in one of the duty-free liquor stores that can be found in almost every strip mall on Grand Cayman, and enjoy a cocktail or nightcap from the comfort of your room or balcony. Cayman customs limits you to two bottles per person. Lunch often offers the same or similar dishes at a considerable discount. Finally, when you are figuring your dining budget, remember that the Cayman dollar is worth 25% more than the U.S. dollar, and virtually all menus are priced in Cayman dollars.