Every year, we explored a different island — until Antigua made us want to stay.

We were booked at the Divi Anchorage Resort on Dickinson Bay between Christmas and New Year’s — one of those places you fall for instantly and start planning the return trip before the first one ends.

The Divi was located steps from the Caribbean, and the views were unreal — turquoise water by day, orange-pink sunsets at dusk, and the sound of the sea at night.

Two of our favorite places along Dickenson Bay were Miller’s on the Beach and Warri Pier. Miller’s served two-for-one cocktails for happy hour. Their pina coladas were outrageously delicious any time of the day. 

I booked a private trail ride at the St. James’s Club.  At least three people at the breakfast buffet asked me where to go riding on the island.

I arrived at the stable early and waited for the guide. In the distance, I saw a young man on horseback heading toward me, ponying two beautiful, palomino Quarter Horses.    

Andrés looked like he’d stepped straight off the cover of a magazine — long blond hair pulled into a ponytail, an easy smile, and the relaxed confidence of someone who had spent most of his life in the saddle.

The ride began on dusty trails winding through the hills behind the resort, the kind of landscape where the air smells faintly of sunbaked earth and salt drifting in from the sea.

Somewhere along the trail, Andrés casually mentioned he was an Argentinian polo player. Because apparently, this was no longer a normal trail ride.

We rode through the hills talking about horses, riding, and island life until he asked, almost offhandedly:

“Have you ever played polo?”

I laughed and told him no.

“We’ll have to fix that,” he replied.

At the end of the ride, we returned to the stable where Andrés untacked the horses. Then, he offered me a leg up onto his horse and hand-walked us down to a quiet stretch of empty beach.

I could never quite figure out why his white shirt needed to be unbuttoned half the ride — but I wasn’t exactly complaining. It was, without question, top-tier island eye candy.

Waiting there beside the surf was a polo mallet and ball.  I quickly surmised that this was Andrés’ practice field.

And just like that, my trail ride became my first polo lesson.

Because I already rode and had good balance, I picked up the basics quickly. My mallet connected more than once, knocking the ball down the beach while the horse surged forward beneath me.

I was feeling very proud of myself when Andrés decided we were moving into advanced instruction.

What happened next still feels slightly unreal.  He swung up behind me like this was something he did every day.

Somehow, he managed to guide the horse, steady me in front of him, and drive the polo ball down the beach at a full gallop all at the same time.

We flew across the sand in sharp, sweeping turns while the surf exploded around the horse’s legs.

I remember laughing one second and hanging on the next, convinced I was either starring in the most outrageous travel adventure of my life—or about to become an international incident in Antigua.

It was exhilarating.
Wild.
Completely out of my comfort zone — but absolute perfection.

The lesson ended with a long bareback gallop through the shallows, the horse splashing effortlessly along the edge of the Caribbean surf.

Dining with the Stars

Antigua turned out to be exceptional in more ways than one — my first polo experience and an unexpected brush with celebrities.

Staying in one of the beach cottages at the Divi that week was Shari Belafonte and her husband, Sam Behrens, along with their extended family.

They had the long dining table beside ours for the entire week. At first everyone politely nodded over morning coffee and dinner service, but by the third day, we were greeting each other like old vacation friends. They could not have been nicer. 

At one point, I accidentally called Sam ‘Jake’ — the name of his General Hospital character. The reaction was instant: the whole table erupted in laughter, Sam included.

I was mortified, but Shari leaned over, still laughing, and said, ‘Oh, that happens all the time. He’ll answer to just about any name.'”

The Divi hosted a New Year’s Eve party in the open-air dining pavilion overlooking the sea. Music drifted across the water, champagne glasses appeared before midnight, and at one point Shari ended up teaching half the resort how to do the Electric Slide.

Antigua became more than a vacation destination. It felt like a second home and we returned often.

Each visit, I rode the horses at St. James’s Club until the stable closed.  I hiked trails through the hills above English Harbour, spent evenings at Nelson’s Dockyard, and watched sunsets from Shirley Heights. Those beautiful Caribbean places always felt timeless.

My favorite place to visit was Harmony Hall. It combined everything Antigua did well — the setting, the food, and that relaxed Caribbean atmosphere. The old sugar mill buildings and the waterfront location gave it a very different feel from the beachfront destinations.

The gallery there had a strong reputation — especially for Caribbean artists and colorful island-inspired work.

Harmony Hall has since closed in its original form; for many visitors it was a signature Antigua lunch destination. The drive out along the east coast and then sitting there overlooking Nonsuch Bay was part of the island experience.

One encounter that stayed with me was meeting artist, Katie Shears, at Seahorse Studios. A California transplant, Katie told me she had first arrived in Antigua on a sailing trip — and never really left. Before building her life on the island, she had worked as an animator for Hanna-Barbera. I left her studio carrying two of her wildlife prints, and they still hang on the walls of my home — small reminders of a place that quietly worked its way into my life.

Somewhere between the rhythm of the waves and the steady gait of the horse, Antigua became an important chapter in our story.

It slowly stopped feeling like somewhere we visited and started feeling like somewhere we belonged.

Part of the Riding on Vacation Series