48 Hours in Grand Cayman

Travel Features Grand Cayman
48 Hours in Grand Cayman

The Cayman Islands might bring to mind an image of disembarking a cruise to lounge on white-sand beaches spilling into the endless shades of teal water, but Grand Cayman is so much more than a single port on a weeklong itinerary. While the souvenir shop-lined streets of Georgetown are filled with cruise passengers during the day, the town empties at night, making it a quiet destination for those staying on the island. While cruising is a convenient way to see the Caribbean, consider spending a weekend on Grand Cayman to experience all the island has to offer. Just a two and a half-hour flight from Atlanta, the world’s busiest airport, the Cayman Islands are the perfect warm-weather weekend retreat.



2:00 p.m.

The beauty of flying into Grand Cayman is that the island is only 22 miles long. This means the transfer from the airport to Seven Mile Beach, which hosts most hotels like the Grand Cayman Marriott Beach Resort, is no more than 15 minutes. Once you arrive and check-in, drop your bags in the room and change into your bathing suit.

Non-motorized water sports equipment such as kayaks and stand-up paddleboards are provided by the hotel, so hit the water to get moving after the flight. The outdoor pool or the beachfront lounge chairs are also great options for unwinding and soaking up some rays in the afternoon upon reaching the tropical climate. Don’t forget to swing by the poolside bar for a stiff drink to jump-start a weekend of relaxation.


6:30 p.m.

In the late afternoon, meet Red Sail Sports outside of the lobby for a transfer to their dock to board a luxury 65-foot catamaran. After a half-hour sail to reach the shore of Rum Point, climb the ladder down to the waist-deep water and wait for the stingrays to glide toward you. Though they still have their barbs, the animals are harmless and quite friendly. The staff will teach you all about the animals while you hold them, pet them and watch them swim all around their home affectionately known as Stingray City. After an hour or two, the crew will sail back toward the dock with a stop to watch the sunset over light snacks. Order a White Tip from the bar to enjoy a local brew that helps conserve and protect whitetip sharks in the region.

Once on land again, make your way to The Wharf for dinner. The oceanfront restaurant serves delicious, fresh seafood as well as other internationally-inspired dishes. Try to get a waterfront table to watch the school of tarpon swimming at the edge of the restaurant.



9:00 a.m.

Enjoy a leisurely breakfast and coffee before heading out to the poolside Red Sail Sports office to check-in for a Waverunner snorkel session. The staff will provide you with a lifevest, fins, a mask and your own jet ski to skim across the breaking waves to some of the island’s best coral reefs. Arriving at a safe distance, cut the engine and pull on your fins before jumping into the water. Colorful fish swim all around, purple fan coral waves from the ocean floor and brain coral sits below too. This fast-paced and lively morning is an exhilarating start to the day. After moving between two or three coral reefs, return back to the room to shower off and don activewear before heading to Rum Point.


Rum Point feels like a million miles away in its secluded corner of the island. It’s a favorite spot of locals and visitors alike and makes for a picturesque lunch. Take a seat at a Rum Point Club beachfront picnic table and order a banana or mango smoothie for a refreshing pick-me-up alongside a salad or sandwich.

After recharging for a bit and enjoying the view at lunch, meet up with ECO Rides in East End. This quiet, historic district is home to beautiful scenery and ocean views which are best seen while cycling Queens Highway. Take your camera and plenty of water as there are tons of photo opportunities. If you’re lucky, a blue iguana—which is a protected species—will cross your path on the way to the Crystal Caves. The caves were just discovered, excavated and opened for tours in 2016, so this hidden sight is a pristine trek away from the crowds and resort areas.

6:00 p.m.

After hours of easy cycling in the sun, freshen up and head to The Brasserie for dinner. A local favorite, this restaurant is actually located in a business park and is one of the island’s two farm-to-table eateries. The chef works closely with the farmer (who is also his wife) to prepare thoughtful dishes from their raised gardens’ crops. The grounds have everything from a red banana tree and coffee tree to papaya trees and fresh greens. Order anything that features their local starfruit or coconut, but the truffle grilled cheese is drool-worthy.



9:00 a.m.

Rise early with an espresso and fresh juice from the lobby’s Anchor&Den before venturing out to the beach for one last sandy morning. Go for a swim and lounge on the anchored off-shore floats or pick up a paddleboard for a relaxing morning workout. There’s plenty of time to enjoy the beach and ocean one last time before showering off, packing and heading for the airport.

11:00 a.m.

Check-out and bid farewell to Marriott’s Beach House Experience, which keeps visitors feeling at home and entertained with many interactive opportunities, and transfer to the airport. Most flights are not until mid- to late-afternoon, so stop by Caymana Bay shopping center to pick up souvenirs like locally-inspired books for children or Cayman sea salt for cooking back home. The tropical destination is so much more than a single cruise port, and a visit to the island itself exposes a whole new side of the Cayman Islands to those who come to stay.


Molly Harris is a freelance journalist. You can often find her on the highway somewhere between Florida and North Carolina or taking life slow in Europe.

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