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A Gourmet’s Tour of the Cayman Islands
An unforgettable dish requires two things: delicious ingredients and a chef who knows all the secrets to preparing them so their flavors shine. In the Cayman Islands, these ingredients include fish, conch, and other shellfish from the sea, along with an abundance of fresh produce—thanks to the rich soil and year-round sunny days. The chefs include everyone from local cooks who follow recipes passed down through the generations to internationally trained ones who have added sophisticated and cosmopolitan offerings to the islands’ culinary scene. On this five-day itinerary to the Cayman Islands, you’ll have opportunities to savor it all from local favorites to white-tablecloth dining by the sea though given that there are more than 200 restaurants in the islands, this trip may end up just being your first course.           

Note: There are a number of festivals and events on the culinary calendar of the Cayman Islands, and you may want to time your visit to coincide with one of them: Taste of Cayman (January), Cayman Cookout (also in January), and Cayman Restaurant Month & Cocktail Week (October).
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    Kimpton Seafire Resort + Spa
    Photo By Kimpton Seafire Resort + Spa
    Day 1
    Welcome to Grand Cayman
    After you land in the Cayman Islands, you’ll make your way to your home base for your culinary adventure. The Retreat at Lookout Farm is an appealingly quiet choice: The eight-unit property sits amid landscaped gardens and the fields of a working farm with neat rows of mangoes, papayas, and breadfruit. Even if you don’t stay at Lookout Farm, you’ll likely taste their fruit elsewhere during your trip—they supply many restaurants on Grand Cayman. Note that it’s located in Bodden Town, the islands’ original capital, roughly 30 minutes by car from Seven-Mile Beach. If you’d rather be in the heart of the action, the Kimpton Seafire Resort + Spa is a good choice. The newest hotel on Grand Cayman, Seafire opened in 2017 and has already become a favorite with its landscaped grounds, water views around every corner, and three excellent restaurants.

    After getting settled in, head into Bodden Town if you are staying at the Retreat at Lookout Farm. Your first meal in Grand Cayman is likely to be your cheapest, but it may also end up being the best. Rankin’s Jerk Pit is a no-attitude place that specializes in one of the Caribbean’s signature dishes, jerk chicken—grilled after being marinated for hours in a sauce of chilis and spices. The setting is casual and you may have to wait a while for your cooked-to-perfection dinner, but that’s OK, you are now on vacation and island time.

    If you are staying at the Seafire, start your first day with dinner at one of the resort’s three restaurants. Don’t worry, you’ll have three more nights to explore options off-property. At Avecita, the dinner-only exhibition restaurant within the larger Ave restaurant, you’ll have a front-row seat on the kitchen, where the crew creates masterful renditions of Spanish tapas under the direction of Chef Massimo De Francesca. Or you can choose the more casual Coccoloba, a casual joint with ocean views.
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    Day 2
    To Market!
    A visit to a farmer’s market is an ideal introduction to the culinary riches of almost any destination, and Grand Cayman is no exception. At the Market at the Cricket Grounds, open every day except Sunday, you’ll find farmers offering a bounty of fruits and vegetables, from an astounding variety of mangoes to other ingredients you may never see back home like callaloo (Caribbean spinach) and cassava. There are often performances by local musicians while you can also shop for local crafts like woven straw items and soaps, perfume and jewelry made from caymanite.

    When it’s time for lunch, Harbour Drive along the western edge of George Town offers an array of waterfront restaurants to choose from. Or if you want to sample a signature Caribbean dish, head inland to Singh’s Roti Shop, a local favorite. The flatbread is more commonly associated with islands like Trinidad and Jamaica, but this roti shop reflects the fact that, as a major financial center, the Cayman Islands has drawn immigrants from around the world, including neighboring islands.

    Any culinary itinerary should include an introduction to the drinks served alongside the dishes. This afternoon you’ll visit the Cayman Spirits Co., one of the islands’ small-batch distilleries. You’ll learn about the process of making award-winning spirits, including the company’s acclaimed Seven Fathoms Rum, as well as vodka and a range of liqueurs. At the end of the tour, you’ll have a chance to sample the products. At the Cayman Islands Brewery, the tours every hour include tastes of five different beers.

    For dinner tonight, head to the northern tip of the island to Catch Restaurant. This restaurant features the very freshest fish possible, served in a variety of dishes—ceviches, sashimi, and local chowders.
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    Day 3
    To Sea!
    At the heart of Caymanian cuisine is fresh fish, and no wonder when the waters here teem with marlin and mahi-mahi, sailfish and snapper. For many travelers, deep-sea fishing is the primary reason to visit the Cayman Islands. Even if you rarely cast a line at home, your charter today will provide an introduction to the marine bounty of the islands. While what you can reel in varies with the season, there are deep-sea excursions offered year-round. If you’d prefer to look at the fish from behind a mask on a snorkeling trip, there’s an abundance of options including ones that stop at Stingray City, sandbars on Grand Cayman’s North Sound where you can snorkel or dive alongside the stingrays.

    This evening you’ll return to George Town for dinner at the Grand Old House, the oldest fine-dining establishment on the island. Located in a colonial-era house from 1908, the menu is eclectic with curry and conch fritters, pastas and Caribbean lobster salads, but the ingredients are always as fresh as possible and the only things that can compete with the food for your attention are the stunning setting and views.
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    Day 4
    A Local Culinary Tour
    You’ll head out this morning on a private tour with Caribbean Culinary Concepts that will introduce you to some of the flavors of the Cayman Islands that are at once typical (for the islands) and surprising (to visitors). As this will be a private tour, it can be customized around your interests (and dietary requirements), but you may sample lionfish sandwiches, rum cakes, curry goat, and other local dishes. The tour also includes a stop at a local gallery—there is, after all, more to Caymanian culture than just its cuisine.

    After an afternoon enjoying some time by the pool or splashing in the sea, you’ll end your Caymanian adventure with dinner at one of its most celebrated restaurants, Blue by Eric Ripert at The Ritz-Carlton, Grand Cayman. Given Ripert’s passion for seafood, it’s fitting that he opened an outpost on Grand Cayman. It’s the only AAA Five Diamond restaurant in the Caribbean thanks to its exquisitely presented and prepared six- and seven-course dinners that showcase the very best fish and shellfish available, divided into “Almost Raw,” Barely Touched,” and “Lightly Cooked” menus.
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    Day 5
    Depart
    This morning you’ll enjoy a final breakfast of mangos and papayas, and perhaps one of your new favorite local dishes like johnny cakes or fritters. Then, before you head to the airport, you may want to stop by Camana Bay, the island’s main shopping destination, where you can pick up a Caymanian cookbook at Books & Books or some local hot pepper jelly or Caymanian sea salt at Bay Market or Bon Vivant. Even though your vacation may be coming to an end, you can continue to explore the flavors of the Cayman Islands once you get home.