Living Like a Local In Grand Cayman

Jason Kennedy shares his favourite places in this Caribbean hot spot 

In 2008, artist Jason Kennedy traded Toronto for Grand Cayman. His notable artwork includes a playful mural on the side of Cayman Cabana, a downtown restaurant and bar. “You can’t miss it,” says Kennedy. “It’s like building, building, boom! Artwork.” Here, Kennedy offers a local take on one of the Caribbean’s hottest destinations. 

Best Beach

“Seven Mile Beach is a natural beauty and the water is incredible at all times,” says Kennedy of the beach that is consistently rated one of the best in the world. But Kennedy says South Sound’s Smith Cove is a true hidden gem. With powder-white sand, reef heads and iron shore formations on each end, “it’s really good for snorkelling.” 

Where to Dine

“Vivine’s Kitchen is a spot you have to hit when you come to Cayman for actual Caymanian food,” says Kennedy. A fan of Italian food, he regularly dines out at La Dolce Vita in George Town. The custom-made pizza oven there “produces incredible pizzas and fills the restaurant with an amazing aroma; it’s the only one of its kind in Cayman.”

Where to Brunch

“Brunch is a big deal here,” says Kennedy. “All the hotels do brunch, but Luca Restaurant at the Caribbean Club is the place to go; their Sunday brunch selection is vast and their ceviche is a treat.” 

For Sunset Cocktails

According to Kennedy, there is nowhere better to watch the sunset than under My Bar’s thatched roof cabana at Sunset House, located just south of George Town. “The cocktails are amazing,” he says.

Best Hiking Trail

The Mastic Trail at the National Trust’s Mastic Reserve & Trail in Bodden Town. “People love that it’s rocky and treacherous,” says Kennedy, who recommends good footwear for the iron shore terrain. 

Where to Stay

“Anywhere on Seven Mile Beach,” says Kennedy. Or, to get away from the hustle and bustle, head to Morritt’s Grand Resort in the cultural district of East End. “It’s rustic, has an infinity pool, a great pool bar and really cool bartenders.”

Best Day Trip

Rum Point is around 50 minutes northeast of George Town. “It’s the farthest point you can drive to,” says Kennedy. Pack your stuff and make a scenic stop at The Grape Tree Cafe in Bodden Town “for a bit of fish fry.”

Culture Stops

Kennedy’s artwork has been exhibited in galleries throughout the island. “I don’t have a favourite,” he says. “Every one is unique.” Currently, his work can be seen at Kennedy Gallery (no relation) and Pure Art. For local art and historical pieces, “check out The Cayman Islands National Museum; it’s the only one of its kind.” 

Grand Cayman Highlights

Swimming with turtles, snorkelling Bloody Bay Wall on Little Cayman and caving on Cayman Brac. It’s all about “getting the full Caymanian experience,” says Kennedy.