A Beginner's Guide To Grand Cayman: Where To Eat, What To Do, And Where To Stay

The Cayman Islands are, in many ways, a vacationer's dream. Pristine beaches, natural beauty, and a robust economy have led to a building boom as more and more travelers realize that its luxurious hotels, spectacular restaurants, and ample opportunities for outdoor adventure make it an ideal getaway for couples and families alike.

Grand Cayman is a large island, but the island's commercial district can be found along its west coast, where the waterfront of George Town (its capital city) boasts ample restaurants and attractions, and Church Street and Bay Road run adjacent to the water and lead to many of the most popular hotels.

On a recent trip to the island at the invitation of the Cayman Islands Department of Tourism, we stayed at the Grand Cayman Marriott Beach Resort, which was luxurious, comfortable, and perfectly situated right on the famed Seven Mile Beach and just a few minutes' drive from George Town's main waterfront drag, Harbour Drive. Our room overlooked the beautiful pool area, a waterside bar and restaurant, and the ocean beyond. Its lobby also boasts a lovely restaurant, Den, which serves breakfast and dinner and also has a bar that was very popular. The Marriott is right up there with all of the island's other top hotels, including the Ritz-Carlton, the Kimpton Seafire, and the Westin, and we'd recommend it without reservation.

Grand Cayman is home to a wide variety of restaurants, and just about all of them provide ample opportunities to sample the island's native cuisine, which is obviously seafood-heavy: tuna, snapper, mackerel, lionfish, mahi-mahi, and turtle are all popular proteins, and conch is omnipresent, either in soups, fritters, salads, or thinly sliced and deep-fried. (It has a mild flavor and texture similar to calamari.) Traditional Caymanian fare is simple and showcases the high quality of the local ingredients; many dishes are simply topped with a spicy traditional Caymanian sauce made of tomato, onion, vinegar, and local chiles that are simply referred to as seasoning peppers. The best advice for dining out on Grand Cayman? Stick with local seafood and traditional preparations whenever possible, and you definitely won't be disappointed. It's the Caribbean, after all!

We asked lots of locals where they like to eat, and without fail we were pointed to two restaurants: Chicken! Chicken!, which specializes in chicken simply roasted over wood; and Cayman Cabana, which serves traditional Caymanian and Caribbean fare on a patio overlooking the water. Craft, a straight-ahead gastropub, is a great option if you're looking to sample some local beers (try Caybrew, an easy-drinking lager), and dishes like poutine, a dry-aged beef burger, fish and chips, and falafel make for a nice change of pace. They also make a spectacular chicken curry (served over rice, fries, or both), one of the best (and most gutbusting) things we ate on the island.

Guy Harvey's is located right in the heart of George Town, and is very popular with locals and tourists alike; its breezy décor and wide variety of Caymanian classics, salads, sandwiches, and sushi make it an ideal lunch spot. Icoa, located in a strip mall a short walk from the Marriott, is a casual and bustling breakfast and lunch spot, and is known for its wide variety of house-made breads and pastries. And the tropical-themed Peppers, located right across the street from the Marriott, is a fun and casual restaurant and bar that's known for its tropical drinks, jerk chicken, and baby back ribs.

Grand Cayman is also home to a large number of fine dining restaurants (which can get very pricey, as the Cayman dollar is stronger than the American dollar; all businesses accept both forms of currency, though), and we had the opportunity to dine at several of them. Grand Old House is indeed located in a grand old plantation house right along the water, but the spacious dining room is located entirely outdoors. The seafood salad is a great way to start the meal, loaded with octopus, shrimp, squid, and local wahoo in a spicy lime-coconut sauce. Bacon-wrapped local wahoo is a smart entrée to order, perfectly cooked medallions of fish with a shrimp risotto and coconut beurre blanc. Jumbo shrimp from Florida were served with saffron risotto and mango-pineapple salsa, and were literally the biggest shrimp we've encountered in our entire lives.

Lobster Pot is one of the island's best-known restaurants and has a bustling bar, dining room, and patio (also overlooking the water). Its menu proudly lists its local produce purveyors, and there's no shortage of opportunity to sample local ingredients, from Caribbean lobster to queen conch, Cayman turtle (served as a "steak" topped with that traditional Cayman sauce), and catch of the day served in ceviche, grilled, blackened, Cayman style, pan-fried, or escovitch. Other (non-local) specialties include escargot, coconut shrimp, Alaska king crab legs, and filet mignon.

Agua is an Italian restaurant located in Camana Bay, a new self-contained development of shops, bars, restaurants, and apartments that's quickly becoming one of the most popular places to live on the island. (Camana Bay is worthy of a visit in its own right; more on it below). The restaurant is sleek and inviting, but we'd recommend grabbing a table outside on a nice night. Of course, you can't go wrong with seafood (much of which is wild-caught by local fisherman), in preparations including Sicilian-style mahi-mahi, Ligurian-style snapper, or simply grilled. We'd strongly recommend you sample the ceviche, of which six styles are available, and there are also eight house-made pastas on the menu, including Caribbean lobster ravioli, pappardelle with lamb Bolognese, and tagliatelle with tuna crudo and anchovy butter. We decided to take this opportunity to have a non-seafood meal, and were rewarded with a perfect plate of cacio e pepe (housemade maccheroni with black pepper and Sardinian pecorino); juicy, crispy-skinned mattone chicken with creamy potatoes and brown butter; and perfectly cooked skirt steak with a super-flavorful salsa verde. We also sampled a few of the ceviches on offer, and were really impressed by them as well (especially the Nikkei, with tuna, yuzu, tamarind, soy, and cilantro).

Calypso Grill, located off the beaten path in West Bay, is one of the most beloved restaurants on the island, and our dinner there was the best meal we had during our trip. The dining room is funky and eclectic, and gentle breezes blow into the space from a tranquil harbor over a charming patio. Chef George Fowler sources fresh seafood from boats that pull right up the restaurant daily, and everything is prepared with a deft hand and attention to the small details. The menu changes daily, but you can't go wrong with the cracked conch (which is sliced super-thinly, lightly battered, fried, and served with a squeeze of lemon), lobster and shrimp Champagne (shrimp and local lobster in a Champagne cream sauce), and fresh grouper topped with spinach and a crab cake.

Other favorites include wahoo escovitch, duck confit, crispy shrimp in a mango-rum sauce, seafood linguini, and grilled rack of lamb in tomato butter sauce. When we visited, the fresh catch included tuna, black grouper, wahoo, and mahi-mahi, and it can be prepared blackened, grilled, or sautéed. No matter what, make sure you finish your meal with chef Fowler's now-legendary sticky toffee pudding (his cookbook is even called "Going Down Sticky Toffee Lane"). And as icing on the cake, Calypso Grill also prepared the best cocktails we had on the island, and had far-and-away the most expansive wine list. It's a must-visit.

And if you happen to be on the island on a Sunday, you also owe it to yourself to try the Sunday brunch at Luca, a stylish and modern Italian restaurant located in the exclusive Caribbean Club. One of the island's true hidden culinary gems, this brunch really has it all, including eggs Benedict; omelettes and pastas made to order; a carving station with roast pork, lamb chops, ribs, and beef Wellington; breakfast pastries; ham, sausage, and bacon; cheese and charcuterie; dim sum; sushi; fresh seafood; and a wide assortment of desserts; all washed down with all the sparkling rosé you care to drink. And at 65 Cayman dollars, it's a steal.

If Grand Cayman were to have a "downtown," it would most likely be George Town's Harbour Drive. This is where cruise ships dock, so there's an assortment of tourist-friendly shops and restaurants (including Guy Harvey's, Hard Rock Cafe, a huge Margaritaville, and a large bar called Sharkeez). While a visit can certainly occupy a few hours (and a stroll along the waterfront is always a good idea), this remains a largely residential area. We suggest you visit Harbour Drive for lunch and a walk around the area, but don't expect to spend the bulk of your trip here.

Instead, there's plenty to do that's only a cab ride away. There's no shortage of opportunities for some of the world's best scuba diving, of course. The famed Crystal Caves (spectacular underground caves surrounded by undisturbed rainforest) are a must-visit. The famed Seven Mile Beach has plenty of public access points. Starfish Point is a pristine beach that's home to hundreds of starfish. And if you have even a passing interest in turtles (who doesn't?), then you must visit the Cayman Turtle Centre, a conservation facility, breeder, and attraction where you can learn about (and hold, and swim with) Green Sea Turtles and interact with other local wildlife including the Cayman parrot.

One additional activity that every visitor to Grand Cayman should experience is a trip to Stingray City, a sandbar that's home to dozens of friendly sting rays (called the "puppies of the sea." We booked our visit through Red Sail Sports, which brought us to the city (as well as an adjacent coral reef for snorkeling) in a comfortable 65-foot catamaran. While you stand in shallow water, sting rays come by to say hello, and a photographer is on hand to take photos of you holding them. It's a little jarring at first (especially when they brush up against your leg when you're not expecting it), but everyone in our group quickly got used to them; it's one of the most memorable wildlife encounters you'll ever have (cocktails on the boat on the way back are icing on the cake). Many other stingray cities have popped up in the Caribbean, but Grand Cayman's is the original, and still the best.

While on Grand Cayman, you owe yourself a visit to the aforementioned Camana Bay, where Agua is located. It's its own self-contained little town that has an urban, modern vibe and is full of young families and vacationers, with enough to do that you can easily spend a full day there — which is part of the reason why apartments there are among the most in-demand on the island. Aside from delicious Italian food at Agua, there are also dozens of shops, including a bookstore, furniture stores, a Polo outlet, and jewelry stores; the island's only movie theater; a farmers market; a 75-foot observation tower; plenty of secluded courtyards and waterfront nooks; and dining options including a French bakery, a traditional English pub, a New York-style pizzeria, an Indian restaurant, a sushi spot, a wine bar, and a small plates/cocktail bar. It's also home to a great kitchenware shop called Bon Vivant, so well-curated that it gives Williams-Sonoma a run for its money. In the rear of the store is a state-of-the-art kitchen where you can take a hands-on cooking class; we had the opportunity to tie on our aprons and cook with local chef Maureen Cubbon, who helped us whip up callaloo eggs Benedict and a plantain waffle while learning about local produce and cooking techniques. If you enjoy cooking and want to learn about traditional Caymanian fare, make sure you check out one of these hands-on classes.

We were fortunate enough to visit Grand Cayman during its annual Pirates Week, which added a whole new layer of fun to the weekend. Centered around Harbour Drive, Pirates Week has been a favorite among locals and tourists for over 40 years and boasts a full calendar of activities, including costume contests, a big food festival featuring traditional Caymanian fare, fireworks displays, a dog costume parade, and sporting and dancing competitions. It seemed as if the whole island came out for the main event, a mock pirate invasion in which dozens of locals dressed in their finest pirate garb steered a pirate ship into the main harbor (complete with cannon fire for the full effect) and captured the "governor" and several redcoats before joining up with hundreds of additional pirates and parading down Harbour Drive with floats and bead tossing. Needless to say, this was a huge amount of fun, and the participants clearly take it very seriously. If you can swing it so your trip coincides with Pirates Week, you'll be amply rewarded.

Grand Cayman is a beautiful island, with a low-key and relaxed vibe that you'd expect from such a legendary Caribbean destination. There's no shortage of things to do, from watching the sunset in the ocean to swimming with turtles and stingrays to having a world-class meal on the waterfront. There are ample luxury hotels and high-end restaurants, but there are also plenty of inexpensive places to stay and local restaurants serving simply prepared traditional fare (and a taxi is never more than a phone call away). There's a reason why so many new apartment buildings and hotels are being built there currently: You'll be planning your next visit before you even leave.

The trip that was the subject of this article was provided at no cost to the author.