Horseback Riding Adventures from LA to Montego Bay

My vision of starring in an equestrian themed couture campaign were dashed upon the realization that my initial horseback riding experience was more congruent with that of a spaghetti western!
03/05/2012 09:58 pm ET Updated Dec 06, 2017

I've always straddled the line between astonishment and deep bone curling fear when observing creatures of flight. Strikingly gorgeous in their stature, long legged grace and force, it is those precise qualities that thoroughbreds posses that cradled my fear of riding. Sure, most women have had fantasies of flawlessly taming and navigating a stallion through a rocky terrain -- complete with a razor sharp blazer, golden Ralph Lauren riding boots and shiny free flowing hair. I was no different.

My vision of starring in an equestrian themed couture campaign were dashed upon the realization that my initial horseback riding experience was more congruent with that of a spaghetti western! Growing up in the city of Los Angeles, California ranchers were not merely spotted on studio lots; their stables were simply a car drive away. Black and brown cowboys were not novelty items -- showcased during Wild, Wild, West elementary school assemblies -- they lived nearby, invested in stables, competed in local equestrian shows and hosted Western and English-styled riding lessons for young black girls, like me, who remained confident that if Pam Grier could boldly lasso her way to female empowerment, so could I.

Bumping our pre-teen obsession -- The Boys' late eighties smash "Dial My Heart" in her mom's Volkswagen Rabbit, my childhood comrade, Heather, filled me in on her riding adventures, the do's and don'ts for first time riders -- (Do #1 -- know that the horse will always have his eyes on you) and details about her posh Sweet Valley High-esque private school clique that racked up ribbons competing. Arriving at the ranch, Heather was treated like royalty. Promptly escorted from the car to the saddle of "Big Blue" she garnered applause for her poise while trotting, jumping and galloping to glory as I watched in amazement from afar. All of her pep talk was suddenly lost in translation, as "Big Blue" quickly became synonymous with the "Headless Horseman's" stallion to me -- way too big, much too monstrous and all too real! Handing me the bridle, I froze in fear. Shaking intensely, I bravely guided "Big Blue" along a dusty path, until he began bucking wildly (likely out of boredom). I instantly abandoned the beloved beast and high tailed it to the car -- running as fast as my denim Keds could take me, sweating profusely, not looking back.

After entertaining nightmares for weeks, I attempted to shatter my bronco anxiety by enrolling in a horseback themed riding camp, sponsored by my fearless Girl Scout troop. (Amazing what one would do for a glowing ribbon, badge or a merit of distinction). My attempt for reconciliation with Mr. Ed was cut short after witnessing a temperamental thoroughbred launch my fellow Thin Mint peddler from his back and into the woods during an afternoon practice. As our hyper pepped troop leaders encouraged us to "keep trotting" while they tended to her wounds, I silently concluded -- "I'm done... just done."

Throughout the years when I encountered horseback riding ventures, I either gently declined or outwardly faked it. Moons later, a date "surprised" me with his idea of a romantic outing- horseback riding through the mountains. Most would have swooned, I kindly asked to be led by a handler for the entire ride, mounting the horse in a12th century princess sidesaddle fashion -- with both legs on one side of the pony -- in case of the need for a quick getaway, jump and roll. Needless to say, that was our last date.

Reminiscent of the character Charlotte from Sex and the City, who tabled her terror of riding by boldly silencing her inner childhood chatter, I knew that the time would come for me to bow to "Big Blue." In the company of Ocean Style TV viewers, I met Pringle -- a former racehorse who now spends his days treating visitors to land and sea jaunts at the famed Half Moon Resort in Montego Bay, Jamaica. A retreat historically frequented by international royalty, John F. and Caroline Kennedy and in recent times -- Venus and Serena Williams, as the spring solstice blooms, Half Moon's stables are expected to bustle with activity. Given the unique opportunity to report on luxury travel and the lifestyle that it affords, provided a dynamic outlet to conquer my equestrian challenges.

Half Moon's promise? Whether you're experienced in the saddle or a first time cowgirl riding at Half Moon Resort in Montego Bay can take you from sheepish to a showstopper!