When it Rains, It Pours: Going Back to the Beginning in Grand Cayman

I was a little nervous about returning to the Cayman Islands.

First, I was nervous it might kill me a little to go back, because it’s such an emotionally charged spot for me. I spent a happy summer here with the love of my early twenties, a relationship that would eventually turn my heart and life inside out. I wondered if coming back might stir up old memories turned toxic with hindsight.

Then, I was nervous that getting there might actually kill me — like, all the way dead — to go back. The storm that had cast a literal cloud over my time in Roatán was following me across the Caribbean, and as I spent my final night in Central America holed up in the unglamorous transit hub of La Ceiba (not in my original plan, but with airports and ferries shutting down in Roatán I had to flee the island early to make my international flight), I obsessively followed weather reports, trying to determine if my plane would make it off the runway.

There are just two direct flights from Honduras to the Cayman Islands per week, and if mine didn’t take off, I’d miss Batabano — the festival that was bringing me back in the first place. Eager as I was to get out of La Ceiba, the rickety ride that had gotten me there was one of the most unnerving flights of my life, and I wasn’t looking forward to being in the air again.

The amazing news, ranked in order of amazingness: (1) My flight arrived in Grand Cayman safe and sound, if a little bumpy. (2) I got to spend a week with Heather, one of my favorite humans, and Sabai, one of my favorite canines. (3) The rain held off for Batabano, one of the most fun days of my year — a day you’ll be hearing a lot more about.

The less-than-amazing news? The rain came right after the last feather from Batabano was swept off the streets, and it didn’t relent for six days straight.

Day after day, we crossed our fingers for a few hours of sun. We hopped in the car to drive to Rum Point during a seeming bright spot only to turn around when we arrived to torrential downpour, we debated on weather or not to head to the beach when we saw a break in the clouds, we wondered if it was worth it to go diving when we’d spend the boat rides wet and freezing.

Time is the greatest luxury I’ve had on Grand Cayman, so I certainly can’t complain that I haven’t seen the island in all its sun-shiny beauty. I most certainly have. And luckily, girl talk and silly giggles aren’t weather dependent. But Heather and I are both certified vitamin-D addicts, and at this point it had been nearly two weeks since I’d seen the sun. Melancholy, mixed with memories, was setting in.

And then, something wonderful happened. On my final day on Cayman, the cloudy fog lifted and the sun came bursting out from its hiding place. The palm trees swayed a little prouder, the sand shone a bright white, and the water glistened the same turquoise as my favorite shade of pedicure polish.

Submerging myself, finally, in the ocean, I remembered — I remembered this island that played such a big role in my story.

I remembered beach days soaking up the sun with new friends. I remembered meeting my boyfriend — a label I’m so hesitant to affix these days, but was so innocently enamored with back then — after work to swim across Smith’s Cove. Driving up to the North Side on his days off to do crazy bounce dives off the wall with tanks thrown in the back of a truck. Nights out on all-you-can-drink pirate ships and in strip mall nightclubs, days working in the ocean, weekends showing the island to my family who eagerly made their way down in shifts to visit.

National Gallery of the Cayman Islands, the best cure for rainy day blues

I spent a happy summer here with my first real love, living in a tiny apartment — on this trip I went for a run past it, and was delighted to recall that this potassium lover once lived in a complex called Banana Walk — and getting around on his motorbike and my cheap bicycle. I went from a timid Open Water diver to a confident PADI Rescue Certified underwater videographer. I made friends that still play a massive role in my life today — Heather, my all time favorite travel buddy, Wim, who I’ve since watched get married, move to Hawaii, and become a mom, and Brian, a friend I urged to go visit Koh Tao, and someone who now makes that island feel like home no matter how long I’ve been away.

My old Cayman digs

I shouldn’t have been afraid to return to Cayman. The summer I spent here was a turning point, one massive leap towards a life of travel. You can’t hide from old memories, and I can’t look back on my past and cherry pick out parts that were unpleasant but brought me where I am today — which is somewhere pretty fantastic. I might have first come to Cayman for a relationship that took a lot from me, but I returned for the friends, the lessons, and the beauty that this place gave me. All it takes is one beautiful day to remember it.

Yup, we did attempt one dive — stay tune for the roundup for the funny story of how it failed

It’s amazing, everything you see when the sun comes out.

Next up, something a little lighter and brighter… Batabano!