Iconic & Historic Restaurants in Grand Cayman

Grand Cayman’s culinary scene is top notch and always evolving, but there are some restaurants that have stood the test of time and helped shape Cayman’s dining reputation. For visitors, they offer not only delicious meals but also a taste of Cayman’s history, tradition and charm.

Read on to learn more about some of the most iconic and historic restaurants in Grand Cayman.

Lobster Pot

A George Town classic since 1965, Lobster Pot is Cayman’s longest-running restaurant. In 2011 the original building caught fire, but this allowed them to do a complete renovation and add-on a second story balcony overlooking the harbour. These changes have continued to make it a favourite spot for seaside lunches and sunset dining. Generations of Caymanians and visitors alike have gathered here for their Queen Conch Fritters, Lobster Bisque, Catch of the Day and Caribbean Lobster Tails. While the menu has evolved over the years, it continues to highlight Caribbean ingredients and flavours.

Grand Old House

Built in 1908 as a colonial-era plantation home, Grand Old House was transformed into a fine dining restaurant in 1969. It has been synonymous with elegance and tradition and is a popular destination for weddings, charity events and milestone celebrations. Their seaside deck has the waves crashing under your feet hence why their bar is aptly named On The Rocks. Go for a sunset happy hour or join them for dinner to enjoy their elevated seafood and steak dishes, including their Seafood Curry and Chateubriand for two. Head inside their cozy Wine Bar for specialty wines and a tapas menu. With so many ways for guests to enjoy this historical restaurant it’s no wonder it has remained a staple in Cayman.

Cracked Conch

Founded in 1981 by dive pioneers Bob and Suzy Soto, Cracked Conch has long celebrated Cayman’s seafaring heritage. Overlooking the deep blue waters of Northwest Point, it features a menu that is globally inspired with a Caribbean twist. Dive into a bowl of red or white Conch Chowder, snack on their Cracked Conch or order a Fresh Catch of the Day. The focus is primarily seafood, but there are a handful of meat and vegetarian options as well. Dine seaside on their outdoor decks, but feel free to grab a cocktail inside their air conditioned Bubble Bar beforehand. Their casual restaurant Macabuca sits right on the water below and is popular for divers and snorkellers to grab a quick bite or cocktail after their excursion.

Ristorante Pappagallo

Since 1985, Ristorante Pappagallo has offered an authentic taste of Italy in West Bay. This striking thatched-roof building is surrounded by a lagoon and a bird sanctuary sets the stage for a memorable evening. Inside you're greeted by their quaint bar and large dining room with glass windows overlooking the lagoon. Known for its house-made pastas, seafood dishes, and grilled meats, Pappagallo has been a beloved choice for romantic dinners, family gatherings, and weddings for nearly four decades. It has also become a very popular Sunday brunch spot for residents in recent years, so there are a range of ways to experience this icon.

Rum Point Club

The Rum Point Wreck Bar has been an institution in North Side since the 1950’s but it was only a beachfront, thatch-roofed bar with no electricity. This was in the days before mass tourism, so its origins started more as a spot that locals frequented to hang out, swim and drink. It became popular for visitors over the years and in the 1980’s the world famous Mudslide was invented; simply vodka, Kahlúa, Irish cream and ice blended together. In the 1990’s the site started to get more upgrades with buildings that included a restaurant, bar, souvenir store and dive shop. During the COVID pandemic while the island was shutdown to the world, the owners decided to give it a fresh look. After the refurbishment was completed in 2023, the Rum Point Club still featured a beach setup of loungers and picnic tables, but most of the area is now taken up by their Rum Deck with a variety of seating areas and a shaded 50 foot long bar. The menu has elevated since it’s reopening in 2023 and now features Conch Croquettes, Surf & Turf and caviar-topped Johnny Cakes. Don’t worry, you can still enjoy an iconic burger, saucy chicken wings and jerk platter if you are craving more casual eats. If you’re looking for a cooler location, head into Solis, which has an air conditioned dining room and bar and serve the same menu as the Rum Deck.

Kaibo

A dock and beach hut were rectified on this location 1983 to welcome and serve refreshments to the late Queen Elizabeth II on her royal visit, making her Kaibo’s first customer. From this modest beach bar it has expanded into one of Cayman’s most beloved destinations in North Side. After getting an upgrade in 1999, their two storey building allows for a range of culinary experiences. Their main Beach Bar & Grill has a casual menu with beachside seating and a menu that features wood fired pizzas, grilled snapper and light salads. They also host popular events, such as Luna Del Mar, a monthly feast held under the full moon, and their weekly Barefoot BBQ. If you want a more elevated experience you should head to The Upstairs at Kaibo for their creative tasting menu, rare rum collection and elevated service. Make a day trip out of it by jumping on Cayman Ferries from Camana Bay, a boat trip of 25 minutes across the North Sound versus a 45 minute drive if you are coming from the Seven Mile Beach area.

The Wharf

Set at the southern end of Seven Mile Beach, The Wharf has been a cornerstone of Cayman’s dining scene since 1988. As the sister restaurant of Grand Old House, The Wharf is also known for using fresh ingredients with international flair and has one of the most extensive wine cellars on island. Some favourites include Seafood Linguine, Baked Bone Marrow and Slow Roasted Rack of Lamb. It has a waterfront setting and it’s known for its nightly tarpon feeding that is enjoyed by visitors. It’s a unique spectacle where the fish gather like clockwork every evening just steps from diners enjoying their meal.

Casanova by the Sea

A favourite since the early 1990s, Casanova by the Sea offers an energetic, welcoming atmosphere in George Town. Perched right over the water, it delivers all the Italian favourites you could crave—pastas, pizzas and seafood. It was affected by Hurricane Ivan in 2004 and took two years to rebuild. Diners can choose to eat inside, opt to sit out on their raised patio or down by the sea where the waves lap at your feet. It’s a family favourite for birthdays because the staff sing an opera-style ‘Happy Birthday’ with tambourines that always has other guests joining in.

The Brasserie

In 1997, The Brasserie changed Cayman dining forever by pioneering the farm-to-table movement. Long before sustainability was a buzzword, The Brasserie was growing their own produce in their urban garden and using two of their own fishing boats to supply the restaurant with fresh fish. They now also have an apiary, coconut plantation and henhouse to supply the restaurant. With all of these fresh ingredients at hand, it’s clear why their menu changes daily and adds ingredients that are in season, including local lobster and conch. Besides their regular lunch and dinner menu, they have weekly theme nights, wine tastings with their master sommelier and farm-to-table dinners that feature international chefs. The Brasserie is tucked in the heart of George Town’s financial district and may not have a beach view, but its food exudes freshness and quality in every bite.

Which one of these iconic and historical restaurants are your favourite to visit in Grand Cayman?