Half Moon Resort, Montego Bay, Jamaica.
Half Moon Resort in Jamaica offers a must-do experience — horseback riding and ocean swimming. This is a reflection, and a return, ten years in the making.
In 2015, my teenage daughter and I visited Half Moon Resort just before her college send-off. We had a week full of exciting activities, balanced with relaxation and quality time together before embarking on the next chapter of our lives. During that week, we both experienced the thrilling ocean horseback swim.
For the past ten years, I’ve been dreaming of returning. The swim of a lifetime, as I called it, kept surfacing in my mind — and a voice in my head kept saying, “You have to go back.” Most people can relate to how life moves forward, and other things, other people, other life-changing events take priority. Sometimes, going back to a cherished experience just doesn’t happen.
Last year I tried to convince family members to join me, but they had other places they wanted to go. I reached out to my daughter about returning together, but finding a window she could take off from work never materialised. Going by myself wasn’t something I’d initially considered — but as life kept moving and the desire to return refused to leave my thoughts, I finally decided to take a few days and go back.
With so much time lost during the pandemic, loved ones gone, personal illness, children growing up and moving on with their own lives, and being ten years older, I decided I wouldn’t put this trip off one more year.
Two months shy of exactly ten years, I returned to the resort — this time on my own. What I took away is that being open-minded about a dream ten years in the making is everything. With an open mind and a willingness to build new memories while cherishing the old ones, you can revisit a perfect trip if you accept that it will be the same, but different. Knowing it would be different without my daughter, and going with an open heart, allowed me to once again truly enjoy and relax at Half Moon — and take that exhilarating ocean swim on horseback.
Half Moon Resort beachfront, Montego Bay.
As I pulled up to the resort, the memories came flooding back. The hotel had undergone a significant renovation and change of ownership, but the changes were subtle, and the resort I remembered appeared in front of me just as I’d left it.
As is always the case in the Caribbean, the weather sometimes has a mind of its own. I got lucky with no rain, but the wind had other plans — and it was predicted to grow stronger as the week went on. If I was going to take my horse swim, ten years of dreams in the making, it had to happen the very next morning.
I had made myself a commemorative book of my article from ten years ago and brought it with me — partly to show the hotel staff, but mostly to reread my own thoughts and impressions from that first trip. As I read it for the first time in a decade, I was struck by how immediately my own words pulled me back into the moment, and by the profound power words have to capture a feeling frozen in time:
“On the count of three, we are all going to reach for the manes and pull ourselves up onto our horse’s back. The horses will step onto the seabed momentarily and stand up. Are you ready? Here we go, one, two, three — Grab! shouted our Jamaican guide, or more importantly, the person to whom I had entrusted my life for the last ten minutes while swimming on horseback three hundred yards off the beach in Jamaica’s Caribbean Sea. As we reached the beach after a short trot through the breaking waves, I was smiling from ear to ear, still unable to fully grasp what we had just done. I have ridden on many beaches all over the world, along shorelines, cantered at the water’s edge with splashing hooves and sand spray — but never a ride like this. Absolutely incredible.”
Rereading those words, I was filled with an excitement that transcended imagination for what awaited me the next morning. I felt a little nervous about the wind — and admittedly, about whether my swimsuit would survive the return to shore — but I held onto hope that the ride would still be possible. As I closed my eyes that night, I realised it would be the last night I’d ever have to dream about this ocean swim. Tomorrow, I would finally get to experience it again.
The Swim
Into the Caribbean: the ocean horseback swim at Half Moon.
Ten years earlier, the water had looked like reflecting glass — flat, still, perfect. The morning I returned, the wind had whipped up rolling waves as far as the eye could see. If we were going to go, we needed to go now.
I was slightly more nervous than I expected to be, without my daughter by my side. My guide could sense me tensing up as the waves started to break at our feet. I made a decision: I was going to commit to this completely. A few big waves weren’t going to turn me around.
In the most perfectly timed cliché imaginable, my guide started singing — and it was exactly what I needed. His voice carried with the wind as he sang Bob Marley’s iconic reassurance — that gentle, unshakeable promise that every little thing is going to be all right. I joined him. It almost made me forget the waves, the stingrays, the sharks — and just be present: alive, on a horse, back in the Jamaican sun and sea. And in that moment, riding into the waves, I believed it completely.
My hair got wet this time. I had to work harder to stay with the horse and not let the waves separate us. I also felt, for the first time, the reality of being ten years older — despite my confident “what’s ten years?” attitude going in. But it was worth every moment. It gave me a renewed sense of self, the inspiration to revisit my bucket list, and a reminder that I am still very much the maverick risk-taker I’ve always been. I felt invincible. I did it. It was a rougher ride this time — but I did it.
I texted my family when I got back to my room to let them know I had survived and that I’d be spending the rest of the week on the safe and uneventful beach. They were relieved to hear it.
The Rest of the Week
Founder’s Cove, Half Moon Resort.
I kept my promise. I spent the rest of the week taking peaceful early-morning walks before the resort stirred to life, riding the resort bikes up and down the property — stopping to browse the shops or photograph something that caught my eye. I swam in the pools and in the calmer ocean in front of Founder’s Cove, sheltered from the wind, and retreated to my porch in the afternoons to read, the sound of waves unending just twenty feet away.
I took a flower-making class, had fabulous dining experiences at the resort’s restaurants — some favourite Jamaican staples like jerk chicken and oxtail, and several wonderful evenings at Delmare, their award-winning seafood restaurant with Italian influences, set right on the white-sand beach at Eclipse. Dramatically appointed with local artwork and open to the Caribbean breeze, Delmare is the kind of restaurant that earns its reputation. The freshest catches — red snapper, grouper, shrimp — grilled in a charcoal Josper oven, alongside house-made pastas and a risotto that changes daily. It won Restaurant of the Year at the Jamaica Observer Table Talk Food Awards in 2021, and it’s easy to see why. Reservations are required and it books up — do not leave it until the last night. The trip wouldn’t have been complete without a visit to the spa, and specifically their over-the-water bungalow massage — something else I’d been dreaming about for ten years. With the shutters open, the sheets billowed with each gust of wind, the sound of them mixing with the sound of the sea below. The ocean was visible through the floorboards if I opened an eye. Pure heaven.
The staff was as warm and professional as I remembered. I had lovely conversations reminiscing about my stay ten years earlier, and they made me promise not to wait another decade before coming back. I promised them I’d try.
The over-the-water spa bungalows, Half Moon Resort.
A birthday retreat and a gift to myself. A swim I was lucky enough to experience twice in a lifetime. A revisit to the past, a pause to restore, and a renewed energy to move forward with the next chapter. Unafraid. Clear-minded. Focused. Happy.
So take the trip. Don’t wait. It gave me so much more than the ocean swim I’d spent ten years dreaming about. I remembered what I love, rediscovered who I am, and got clear on what I want from my life — horses, travel, old friends and new ones, and strength, inside and out.
My return trip was different from my first. But I came away with wonderful new memories, new connections, and the satisfaction of surviving yet another ocean swim on horseback. I will absolutely return to Half Moon Resort — and I can promise you, it won’t take another ten years.
Plan Your Visit
Half Moon Resort
Location: Rose Hall, Montego Bay, Jamaica
Airport: Sangster International Airport (MBJ) — approximately 15 minutes by car
Property: 400 acres, two miles of private white-sand beachfront. Jamaica’s highest-rated resort by Forbes Travel Guide
Accommodation: 210 rooms and suites plus 19 private villas, across three resort experiences: Eclipse at Half Moon, Villas at Half Moon, and the newly renovated Hibiscus
Website: halfmoon.com
The Equestrian Centre
Director: Trina deLisser — international show jumper, retired FEI judge, and animal welfare activist with nearly 40 years at Half Moon
Ocean Swim (Surf & Turf): Beach ride with horseback ocean swim. Riders must be 8 or older. Wear a swimsuit under your riding clothes; long pants and closed-toe shoes required for the ride portion. Advance booking strongly recommended — this experience fills quickly
Other activities: Beginner and experienced trail rides, private dressage, jumping and polo lessons, Positive Empowerment groundwork sessions, and Pony Park for children under 6
Hours: Monday to Saturday. Contact the centre to arrange timing
Website: horsebackridingjamaica.com
Contact: reservation@halfmoon.com
In collaboration with Half Moon Resort, Montego Bay.