For the 50+ Traveler

The Cayman Islands, located in the Western Caribbean Sea south of Cuba, are comprised of three islands: Grand Cayman, Cayman Brac, and Little Cayman. They are the peaks of an underwater mountain range. As the name indicates, Grand Cayman is the largest and most popular of the three. Being an off-duty tax haven, Grand Cayman and, in particular, the capital, George Town, will make your eyes sparkle with the tempting shopping opportunities, especially the jewelers offering the most amazing emeralds.

But there is far more to enjoy on Grand Cayman. From the incredible Seven Mile Beach to stingrays, turtles, and lush vegetation in the Botanical Garden, the island is a Caribbean dream. We’ll show you the best places to hang out like a local, to dive and snorkel, hike, shop and eat. We’ll tell you all about the world-famous Cayman Cookout and a bit about a side trip to Cayman Brac and Little Cayman. You’ll enjoy the friendly people and their language: a mixture of English and what’s known as Cayman Creole.

The hurricane season in the Caymans officially lasts from June 1 to November 30. It’s best to plan your visit outside these months, although it’s relatively rare for a hurricane to hit the islands. The last big one was Ivan in 2004, and I have personally seen the enormous devastation it caused. Everything has been rebuilt, and the Caymans expect your visit with open arms.

Things To Do On Grand Cayman

1. Seven Mile Beach

Seven Mile Beach is probably the best-known attraction of Grand Cayman. The crescent-shaped stretch of fine coral sand is actually just over six miles long, but who is counting? North of the capital George Town and located in the western part of the island, this Caribbean marvel of turquoise water and soft sand is best enjoyed by walking the entire length. I have done so on several occasions. Set out early in the morning -- swimsuit and flip flops on, towel in hand, sunhat, sunglasses, and a credit card in a waterproof pouch around your neck is all you need. Walk, plunge into the water for a swim, and repeat. The card is for snacks and drinks along the way. Not surprisingly, Seven Mile Beach is the location of many for the best and most luxurious resorts on Grand Cayman, all with beach bars where you can rest. Between the resorts, you can also admire some very impressive private villas.

Rum Point on Grand Cayman island.

2. Rum Point

Rum Point on the northern side of the island is the ultimate weekend hangout for visitors and locals alike. Imagine a fine, white beach and rather shallow water that makes it ideal for kids, dotted with shacks, serving incredible Creole food, tables and benches in the sand, hammocks, palm trees, and umbrellas for shade. The Rum Point Club offers changing rooms and every kind of equipment for diving and snorkeling, so you don’t even need to bring your own. Ample parking is available nearby. Don’t miss a visit to the Wreck Bar to take pics of two huge wooden signposts, one that indicates the direction of other places in the world and the other with the names of hurricanes.

Sip a mudslide, the famous cocktail made from vodka, Kahlua, Bailey’s Irish Cream, and chocolate syrup, and enjoy the sunset.

Stingray City on the coast of Grand Cayman island.

3. Stingray City

Stingray City is a group of sandbars located 25 miles offshore in the North Sound. It’s a favorite gathering point of the majestic stingrays, which you can swim with and play in water that’s only three feet deep. They may look forbidding, but they are friendly and harmless creatures -- unless you frighten them or step on them when getting off the boat. This is an experience of a lifetime. Note that you need a boat to take you there and will want to make a reservation in advance.

George Town, the capital of the Caymans.

4. George Town

George Town, the capital, is one of the most popular cruise ship stops in the Caribbean. If you happen to arrive on a cruise ship, you are right in the center of the shopping district. Financial services are one of the main sources of income in the Caymans, and you’ll see plenty of banks, law firms, and accountants. There is just one main road that follows the curving shoreline. Be careful when crossing roads in the Caymans -- they drive on the left.

In the heart of George Town, you find the colorful National Museum. You’ll learn about Columbus, who discovered the island in 1503 and named it Las Tortugas because of the huge amount of turtles he found there. The museum also introduces the island’s pirate past and information about Isaac Bodden, the island’s first-recorded permanent inhabitant (born in 1661), and much more.

Rum and the Caribbean are inseparable and, for great insight into this relationship, visit the Cayman Spirits Co. for a tour including some very special tasting.

If the emeralds are out of your reach, there is always Pure Art Gallery and Gifts, where you’ll find an amazing array of local art, from paintings to jewelry made from beads and semi-precious stones.

Queen Elizabeth II Botanic Park on Grand Cayman island.

5. Queen Elizabeth II Botanic Park

For an experience that combines natural beauty, history, and culture, just follow Frank Sound Road to North Sound until you arrive at the Queen Elizabeth II Botanic Park. You can spend an hour or half a day exploring the formal gardens with their abundance of tropical flowers and trees. Watch parrots and have tea (this is, after all, a British Overseas Territory) in the lovely tea house. Go to the lake and look out for the unique blue Cayman iguanas, of which there are plenty. There also is an orchid show and many nooks and crannies to delight a nature lover’s heart. You can either go by yourself or join a guided tour.

The Cayman Turtle Center on Grand Cayman island.

6. Turtle Center

We mentioned that Columbus named the island Las Tortugas when he first landed here, and turtles (tortugas in Spanish) are the main subject of the wonderful Cayman Turtle Centre.

What started in 1968 as a project to breed green sea turtles to later release them into the sea turned into a vast adventure which now includes the breeding of parrots (Ralph and Rosie were the first), plus other birds, iguanas, sharks -- in short, much of the wildlife and sea life associated with Grand Cayman.

Located along Northwest Point Road in West Bay, the center is a lagoon where you can swim with turtles and enjoy many other activities.

The Mastic Trail on Grand Cayman island.

7. Mastic Trail

Here is a rather uncommon nature experience, suitable only for the fit and relatively experienced hikers among you. The Mastic Trail is the only designated hiking trail in the Caymans, a two-mile path through various ecosystems including mangrove swamps, dry forest, grassy savannah, and some rocky terrain, too. It starts near Bodden Town in the eastern part of the island and is reached along Park Sound Road. The trail is not a loop, so unless you arrange transport at the other end, you have to walk back. The trail is named after the mastic tree, an endangered tree that was used for shipbuilding and is nearly extinct on the island. Apart from the great variety of vegetation, birds populate the trail as well as snakes, but luckily they are not poisonous. If you are afraid of snakes, don’t go. This is a no-facilities, no-nothing trail, so in addition to sturdy hiking shoes, bring water.

Best Restaurants On Grand Cayman

Food in the Caymans is based on rice, spices, seafood, roots, and vegetables. Conch stew is essentially the national dish (conchs are sea snails), and conch fritters and soup are also popular. Other favorites are the super spicy jerk chicken, coconut shrimp, jonnycakes (dumplings), shredded beef, and the heavy and sweet cassava cake, which is served as a dessert.

For the best conch stew and other local dishes (including breakfast items) head for the charming Over The Edge restaurant in Old Man Bay.

We already mentioned the Cayman Cookout. Even if you can’t make it to the event in January, the Ritz Carlton Resort on Seven Mile Beach where it takes place is an excellent venue for conch and lobster dishes.

When in George Town, you don’t want to miss a local hotspot for the best jerk chicken: Sam’s Quality Jerk and More.

The best and freshest lobster can be found at Deckers on Seven Mile Beach.

For the ultimate Caribbean food and drink experience, head to the thatched, open-air bar and restaurant simply called My Bar at Sunset House just minutes from George Town.

Pro Tips

  • You’ll be happy to know that Grand Cayman is flat. With the exception of the Mastic Trail, the over-50s aren’t subjected to great physical effort when it comes to getting around. If you rent a car, remember to drive on the left!
  • Time permitting, make your way to Cayman Brac and/or Little Cayman. Cayman Brac -- a nature lover’s paradise with limestone caves, shipwrecks, bluffs, and plenty of wildlife -- is much less visited and rougher than Grand Cayman. Beaches, excellent diving sites, and coral reefs distinguish the quiet island of Little Cayman.
  • There are no ferries between Grand Cayman and the sister islands, but Cayman Airways offer daily flights to get you there.