COVID Escape: Grand Cayman

Sam Elsamman
5 min readDec 19, 2020


As Thanksgiving approached we decided that enough was enough. Did we really want to continue on in New York where restrictions would get worse as the cold weather and holiday season approached or could we plan an escape? Leaving friends and family behind was sad, but practically speaking, we could not in good conscience spend time with them so we made the decision to head down to one of the few COVID free-zones in the world — The Cayman Islands.

The Caymans eradicated COVID early on with draconian lockdowns and effectively closing the island to outsiders. Now it is COVID free and remains that way because of strictly enforced 14 day quarantines upon entry. So once your 14 days are up you are in a world that you have not seen for almost a year — no masks, no restrictions, just people having a good time and enjoying the relaxed lifestyle of pristine beaches and fabulous places to eat and drink.

As of October 2020 the island started a phased reopening focusing on returning residents, property owners, participants in their Global Citizen program, where people work remotely from the Cayman islands and in some cases longer stay visitors that are considered on a case-by-case basis.

The journey was a bit more work than just booking a vacation. We booked our flights with Cayman Airways, who at present are the only authorized carrier into Grand Cayman. They have flights from Miami and London so we had to transit via Miami. With flights booked, we applied on the Travel Cayman portal for government authorization to travel. Authorization came 3 days later and we were good to go.

The arrival process couldn’t be smoother. We received a bracelet and phone to ensure that we honored the terms of our quarantine. After a COVID test and the normal customs and immigration checks, we were whisked off to our condo at Plantana on Seven Mile beach. We had ordered groceries online from Hurleys that were already unpacked and in our fridge and cabinets. Two really slick apps (Bento and Let’s Eat) get you quick deliveries from the top restaurants on the island. The first night we had amazingly fresh ceviche from Agua and a few days later some very authentic tacos from Casa 43. Wine and spirits can also be ordered online.

Units at Plantana have a screened in porch so you can sit outside to sun or just enjoy the views of the beach or the lush gardens. A 14 day quarantine is a serious matter but with Netflix, plenty of electronic toys and some regular exercise within our unit the days passed in no time.

On the 15th day we were taken to a testing location, given a COVID test and by that evening we got the good news that we could cut off the wristband and were now free to enter the Cayman bubble. It was late so we took a walk around the property to admire the Christmas lighting knowing that tomorrow we could head out in earnest to enjoy our new found freedom.

Grand Cayman is a unique destination in the Caribbean. It has some of the most beautiful beaches in the world yet is a real community where locals live and work in harmony with tourists. It is missing the large economic disparities found in many parts of the Caribbean making for a very relaxed and tension-free experience wherever you go. After a year of fretting over COVID it was the perfect antidote

Having been to the Caymans many times, we were in no hurry to pursue the usual attractions such as swimming with stingrays or snorkelling the colorful reefs or the Turtle farm where we last visited with our young nice. Instead we craved normalcy and headed over to Camana Bay, a modern waterfront mall where people live, work, shop and dine to take in a movie. The theatre has luxurious seats with side tables for you wine. Then we settled into what would be our new lives for the months to come.

The cost of living is higher in Cayman because everything has to be imported and given that there is no income tax, the import duties are an important source of revenue. The Cayman dollar is pegged to the US dollar at 1.2 which makes things appear to be closer to what they cost in the US. Food shopping is a pleasure with stores such as Kirk Market are reminiscent of a Whole Foods. The quality is superb with a fantastic selection of fresh local fish as well. Once a week a farmers market sets up at Camana Bay with a selection of fresh local vegetables. For those wanting to splurge on prime meats a new butcher, Carnivore has opened, featuring top cuts of meats.

Grand Cayman is really a comfortable environment and we are glad we made the choice to wait out the rest of the pandemic there. Life feels normal again.



Sam Elsamman

Retired technology entrepreneur who loves to hike, travel, cook and write music.