Why Cayman Islands:
The Cayman Islands are a collection of 3 islands south of Cuba and west of Jamaica. They are a self-governing British territory. The largest island (where 99% of tourists go) is Grand Cayman. The islands are best known for being a tax haven, whatever that means.
I saw a JetBlue sale to various non-stop destinations from New York City. One of those destinations was the Grand Cayman. After doing some research, I realized that the island is very small and that I felt I could see most everything in 2 days. So, I booked the flight out on JetBlue and the return the next evening on Cayman Airways.
I quickly learned that the Cayman Islands are extremely expensive. The cheapest hotel appeared to be $250 US per night! After some serious research, I found an unlisted hostel called Major Rod which only charged $75 per night for a room. I booked my room via Whatsapp.
January 22, 2022: One Strange Island
The flight from New York´s JFK airport to Grand Cayman took 3 hours. As we landed, I could see a bright blue shimmering lagoon! Sure beats New York in January!
Once on the ground, I approached the immigration booth. The man, who seemed friendly enough, seriously questioned my motives for coming to the Cayman Islands. He started asking me lots of questions. Why only one night? Why are you not staying in a resort? What is the phone number of the hostel? What is your job? Why have you visited all these unusual countries?
They apparently have never met a budget traveler before.
After 20-minutes and a lot of chatter with his supervisor, the officer let me in.
As I was renting my car, the skies opened, and it started to rain hard. I figured that this would be a typical 15-minute tropical downpour. But it was not. The rain would continue for most of the day.
The entire western side of Grand Cayman contains the vast majority of the population of the Cayman Islands. There are different neighborhoods and towns, but in reality, it really is all one urban area. After stopping for a Tortuga Rum Cake, I got lunch in a “local” restaurant. There is no true local cuisine, so I ordered Jamaican jerk BBQ ribs.
Next, it was time to get my COVID test to come home. The Cayman Islands have been strict with COVID. Visitors have only been allowed in without a quarantine for 2 weeks. The current protocols require visitors to take antigen/lateral flow tests every 3rd day. To accommodate this demand, there are COVID testing sites are everywhere. As I was only in the Cayman Islands for 2 days, I did not need one for Cayman Rules. However, the US did require a test. I got mine at the Westin hotel, right on the beach. The hotel was nice, but nothing special. I suppose what made it nice was that it was only 3 stories tall instead of a high rise.
It was still raining pretty hard, so I drove over to Camana Bay, a center of the Cayman Island´s immense finance industry. Companies register in the Cayman Islands due to the nearly non-existent corporate taxes and ease of conducting business. More than 100,000 companies are headquartered here, more than the population of the islands. For this reason, the Cayman Islands are the 5th largest banking center in the world with over $1.9 trillion in holdings in 250-ish different banks. Every financial institution you can think of has an outpost in the Cayman Islands. In my short walk around the shopping center, I saw Ernst & Young, Royal Bank of Canada Aon, Scociabank and PWC.
The two industries of finance and tourism account for over 70% of the territory´s GDP in normal times. The presence of the financial industry has made the Grand Cayman the wealthiest island in the Caribbean by a longshot.
Much of the finance business is done in the new Camana Bay shopping center. It is a beautiful outdoor mall except most of the tenants are financial companies.
I stopped into one of the restaurants and grabbed a Caybrew beer to wait out the rain. I sat next to 4 very sunburnt British men wearing tropical resort vacation attire. They were talking finance. I find it very funny that a great deal of the financial chaos in the world is conducted by sunburnt British men in a suburban shopping mall.
The rain was starting to let up, so I drove north. After a disappointing stop at a black limestone formation called Hell, I entered Barker´s National Park. This is the only piece of natural land on the western side of Grand Cayman. There were no signs that I was entering the national park except the road turned to dirt.
After 15 minutes of cruising around, I pulled over on the side of the road and walked to an empty beach. It was so beautiful!
I continued to the point at the very end of the island, which had many mangrove trees. I loved the open dirt roads!
On the way back to town, I stopped at Cemetery Beach, a particularly scenic stretch of Grand Cayman´s world famous Seven-Mile-Beach (which is actually only 6.3 miles long). The sand is a perfect white color. I can imagine that on a nice day, this would be the perfect spot to spend a day.
I then drove to the hostel, which is called Major Rod. I was greeted by a British man who runs the place. He told me that immigration called him when I was waiting to get my passport stamped. They asked him about my nationality, job and why I was coming to the Cayman Islands. Wow!
The man also said that the hostel dorms are full with out of work hospitality workers. They are all out of money and are paying on credit. Wow!
He ended up giving me a discount on my room since I wanted the dorm but had to stay in the private room.
I then drove into the main city of St. George, which is also the port of call for cruise ships. However, due to COVID restrictions, the Cayman Islands are not currently allowing cruise ships, so it is a ghost town. The jewelry shops and overpriced uninspiring restaurants found at cruise ports all over the Caribbean are all closed. Only the Hard Rock Café was open. It was surreal to see such an empty town.
On the outskirts of town, I found a Trinidadian restaurant. Trinidad has one of the best cuisines in the world: it is a fusion of Indian, West African and European food . I ordered a curry conch roti. I would call this a fusion food since conch is not typically part of the Trini diet.
The waitress was from Honduras but spoke with a perfect Trini accent, which I found funny. The lady said that the Cayman Islands have lots of Hondurans – especially from the English-speaking Bay Islands- as Honduras is only a 45-minute flight away. But the Cayman Islands are truly a diverse place. People come from all over the world come to work in the Cayman Islands. Both the hospitality and finance industries draw from a global talent pool. Additionally, because the Caymans have the highest standard of living in the Caribbean, they draw many people from other islands – especially the English-speaking islands.
It was now 7pm and there was nothing to do in town. So, I drove back to the hostel. On the way, I saw a bar packed with people. I decided to park and go in. There was a band playing 90´s and early 2000´s covers (think Green Day and Black Keys) on a platform over the ocean! The bar was full of an international crowd. The bartender was Australian, but they were playing NFL on the TV. The Cayman Islands do not have a crazy night life but at least there is something.
January 23, 2022: Stingray City
After a breakfast of avocado toast, it was time for the day´s big activity: Stingray City, a sandbar where humans can interact with wild stingrays. Stingray City is considered the Cayman Islands´ top attraction.
Multiple companies run boat trips to Stingray City, which is located far offshore. Most tours last between 3-4 hours and include a few other stops. As many cruise passengers typically go on Stingray tours, they are reasonably priced. I paid $30 Cayman dollars (about $36 USD) for the 3-hour tour.
It was a bit difficult to find an operator going during the ideal times, but after emailing numerous companies, I found a boat left at 9:30. My boat included a family from Kansas City, an American male nursing influencer living in Brazil here for a medical procedure, his girlfriend from Texas, and a couple from Trinidad here on a work trip.
After a 30-minute boat ride, we reached a coral reef where we could snorkel. The water was clear and very warm. There were plenty of fish! The reef itself wasn´t so colorful but it was still very enjoyable.
The boat continued for 10 more minutes to Stingray City itself. The sandbar is only a meter deep. As the boat pulled up, about a dozen stingrays encircled us. While the stingrays are technically wild, they have been used to humans feeding them for 40 years. Therefore, they rely on the boats for food. This has raised numerous ethical concerns about Stingray City.
On a typical day over 1,000 tourists visit Stingray City. However, during the pandemic, that number dropped to zero. The Cayman Islands government forced the Stingray City companies to feed the stingrays. They have only recently been able to start giving tours again. The day I was there, there were just 2 boats of tourists.
Just as we docked, the guide jumped into the water and said hello to all his “girlfriends”. As the island music played, he went over an gave each one a kiss and a piece of squid. He then invited us all into the water.
One by one, he picked up a stingray and made us kiss her for good luck. Then he let the stingray massage our backs.
Before heading back, we stopped briefly at a beach with sea stars. Then, it was a 30-minute ride back to the harbor.
The Stingray City experience was surreal and unique. I always enjoy petting the stingrays at aquariums, but to swim with them?! Wow! This was by far the best part of my trip.
It was then time to head home. I drove to the airport and flew back to New York. There was no exit immigration.
The Cayman Islands are different from the other Caribbean islands. The finance industry has created a unique dynamic of extremely wealthy people from all over the world. Because the island is inherently wealthy, they can be pickier with the tourists they choose to have – aka only have super wealthy tourists and cruise passengers who are limited to a tiny sliver of the island and don´t spend the night. This is not a place for a budget traveler.
The highlight of the island was undoubtedly Stingray City. The beaches were gorgeous, but every Caribbean Island has nice beaches.
The food was good but did not feel unique to the islands. Rather, there were high quality cuisines that I can find easily in other places.
The look and feel of the islands remind me of a quieter, more diverse Florida. But many of the houses – especially in the south – could have been plucked straight out of Fort Lauderdale.
In short, I am glad I went, but feel no need to go back. I saw plenty in 2 days. An ideal, comprehensive trip would have taken one more day to see the eastern side of the island and a 4th day to scuba dive. Other ideas to extend are the domestic flights to the two other Cayman Islands: Cayman Brac and Little Cayman.