Note: There is a diving video later on in this post

My trip to the Caribbean began as an “Escape from New York.” I don’t recommend last minute decisions to fly out of the Northeastern US immediately prior to a major snowstorm warning, yet that’s what I did. 7am flight booked from JFK to Grand Cayman direct, I set about trying to find myself a car to take me from Westchester to the airport. Everything for the next morning was fully booked. It seemed I had no way to make it to the airport. Fortunately, around 1am I finally found an independent driver to take me. Three hours later we were off, driving through the pounding snow. 

The plane managed to take off after a small delay for de-icing the plane. Not long afterwards, a plane skidded off the runway at Laguardia and shut that airport down for the day. Nonetheless, I had escaped from New York.

Those who have been there would know the Cayman Islands are expensive. I’d been once before in 2009 for my cousin’s wedding. It was a beautiful homemade affair at the Governor’s Mansion (her dad, my uncle, was then the Governor of the Cayman Islands) where my sister, my cousins and I decorated the gazebos and dinner tables with homemade crafts. I learned the word “thule” for the first time here, but we’d all grown up together making dioramas and haunted houses as summer holiday projects in England and in Japan, so we were used to this–but I’ve gone off on a tangent. The Caymans are expensive, and I thought I’d explore another section of the island, further away from 7-Mile Beach, and booked a place on the Eastern end of the island, a 45-minute drive away—big mistake, as it would turn out.

Upon landing I knew I wanted to get a dive in—I’d never had the chance to dive the Caymans’ famous clear waters and I’d been socked in by 4 months of winter in Toronto. Landing just after noon I found a place that offered a 2pm one-tank dive so I went straight for that. A one-tank dive with equipment rental in Grand Cayman costs over $100 if you add tips—like I said, it’s not cheap. Nonetheless I went straight from the plane to pick up my rental car, then straight on to the dive shop 10 minutes later. The great thing about Grand Cayman is how close the airport is to the sea. Luggage still in my car, I was fresh off the plane and on to the boat. I could only get the one dive in because I had a flight out to Cuba the next day and there is a safety protocol for not diving too close to an upcoming flight.

One giant stride entry and straight into the warm Caribbean waters. It was like tonic for my frozen, miserable soul. The dive itself was unremarkable. I dealt with the typical foggy rental mask, and there weren’t a lot of large creatures to see. One turtle made a half second appearance in the distance before swimming away. Otherwise, there were a few interesting shrimp hiding in the coral, but overall it was lacking in impact. Nonetheless, I was perfectly happy. It had been a while since I’d gone diving and the water felt great.

On the off-chance that he might be down in the Caymans as he was a regular, I called up my friend Simon from my days on Wall Street and he was in fact down on the Island this day. He’d been working on his retirement transition from New York down to these turquoise waters and he was an avid diver. He is also an avid drinker, and predictably we met at a local watering hole in the late afternoon. From there we went to dinner with friends and family of his, and then returned to the bar for rock n’ roll bingo, which was a surprisingly fun game. We nailed a lot of the answers very quickly, but luck did not favor us when it came to lining up 5 in a row. At this point, there was no way I was driving anywhere, let alone 45 minutes over to the eastern side of the island. Like I said, a bad idea. Simon graciously let me stay at his lovely condo.

The next morning I awoke and groggily set about trying to book my night’s accommodation in Cuba. I presumed it would be fairly easy to find a casa particular (a room at a private house). As it turns out, I was wrong. Cuba was in the midst of its busiest tourist season on record due to the mad rush to get in before Obama’s detente led to a forever-changed landscape. 

Here I encountered two failures: one by me, one by Cayman Airways. The first: in my rush to hop down from Canada to New York to the Caribbean, I found that I had not yet put back my American bank card into my wallet. All I had was my Canadian one. Alas I was only able to take out $800 at the ATM in Grand Cayman before heading to the airport. I had a feeling that wasn’t going to be nearly enough for what I planned to do for my week in Cuba—I was right.

In the meantime, here’s a short video clip summary of my dive in Grand Cayman with Don Foster’s Dive Shop.

The second failure was that an hour before the flight was to leave, Cayman Airways employees berated us for not having cleared security, making snide comments: “These people think 1pm departure means 1pm at the gate.” Grand Cayman is a tiny airport. It was barely noon and we were already in the security line. What a joke. By 12:10 we were through immigration and they herded us like cattle on to the plane. I was using the airport WiFi to try to make arrangements for where to stay that night. I was awaiting an answer. I knew that once I got to Havana I’d have no internet or cell phone service whatsoever. But they would not let me wait just a few more minutes, so on to the plane we went and I went into digital darkness, unsure if I had managed to lock in my place or not. I went off the grid in the most abrupt manner. Of course, once we were all on the plane, Cayman Airways decided to hold the plane there at the gate for another hour and a half because one of their flights from Miami was late and it had many passengers on it who were looking to connect to Cuba. They wouldn’t let us back off the plane for obvious security purposes, so the frustration for all of the passengers who were yelled at and made to rush grew. The plane was too far to reach the weak WiFi signal. And to make matters worse, the airline ran out of Cuban visa cards, which would come to be an issue on the other end as well. But that’s another story— one which will come up soon in another post at a future date. Stay tuned!