Category: Riding on Vacation

Tobago: An Episode of ‘As the Island Turns’

On By jeanieelizabethIn Riding on VacationLeave a comment

The year after Barbados, we visited Tobago.

Tobago wasn’t heavily developed. It was quiet, tropical, and known for its beautiful beaches.

At that time, it was the preferred holiday destination for European men traveling with their mistresses the week between Christmas and New Years.

This was not disclosed during the booking process. We discovered it shortly after arriving.

The entire hotel was full of glamorous young women in impossibly short, designer dresses and men who appeared delighted by the arrangement.

It felt less like checking into a Caribbean resort and more like accidentally walking onto the set of a soap opera.

And then there was us. The only two people at the hotel who weren’t part of the cast.

The resort itself was beautiful. The property stretched across expansive grounds overlooking a private beach, and the food was Michelin worthy.

Had the story ended there, Tobago would have been remembered as a peaceful Caribbean getaway.

It did not.

The Dress Code

The most entertaining part of each day wasn’t the beach.

It was dinner.

Every evening, distinguished gentlemen appeared for dinner accompanied by remarkably beautiful young women whose dresses seemed to contain approximately the same amount of fabric as a cocktail napkin.

It was a trend: there was a severe fabric shortage.

Necklines ignored traditional engineering principles.

David and I would sit quietly at dinner watching the nightly parade while trying very hard not to stare.

We failed frequently.

By the second evening, I had stopped studying the menu and started studying the crowd.

By the third evening, I had stopped photographing the scenery and started gathering evidence.

I carried my camera everywhere — dinner, beach, pool bar.

The absurdity never ended, and I knew no one back home would believe me without proof.

At one point, I hid behind a dinner napkin to take a photograph.

Not because I was a spy.

Because I anticipated future credibility issues.

The Breakfast Buffet Triangle

One morning, we innocently headed toward the breakfast buffet.

Three different women were circling the same man like contestants on a tropical reality show.

One handed him a plate.

One poured his orange juice.

One glared at the other two.

I just wanted a croissant.

The Human Diffuser

David went to get drinks while I relaxed by the pool with a novel.

Before I could blink the pool water from my eyes, one of the resort’s more enthusiastic guests appeared beside my chair.

Without warning, he produced a bottle of perfume and attempted to apply it directly to my chest.

As though he were performing some sort of sacred Caribbean blessing ritual.

My reflexes reacted before my brain.

I waved him off. “What?! Eww, no. Wrong woman, Romeo — go find your girlfriend.”

He shrugged and disappeared.

I resumed reading.

A few moments later, I glanced at the table beside my chair.

The perfume bottle was sitting there.

I had no idea whether he forgot it, left it intentionally, or considered it part of his presentation.

I stared at the bottle.

The bottle stared back.

David returned with our drinks.

“Did I miss anything?”

“Just a playboy making the rounds.”

David nodded.

By that point, it felt less like conversation and more like a status update.

The Poolside Incident

Apparently, I wasn’t the only source of confusion.

A gentleman settled into the lounge chair beside mine and immediately moved it close enough for us to share an atmosphere.

A few moments later, an attractive woman in oversized sunglasses stormed over and began yelling at him.

While pointing at me.

Although I didn’t understand the language, the message seemed fairly clear. Who is she?!

I pointed toward David.

“I’m with him.”

The woman stormed away.

The man jumped into the pool.

We relocated to the bar.

Sometimes retreat is the best strategy.

Witnesses Remained on Scene

New Year’s Eve arrived with excellent food, beautiful weather, and a level of entertainment that nobody could have anticipated.

The hotel hosted a New Year’s Eve dinner under the stars.

Tables surrounded the pool.

Champagne flowed.

Live music played.

Everything was lovely.

Until someone’s wife arrived.

What followed involved shouting, pushing, hair-pulling, and a level of public relationship management that would have required several therapists and at least two attorneys.

As someone interested in photography, I felt an obligation to document the unfolding chaos.

As a spectator, I didn’t want to miss a second of it.

As a woman enjoying a perfectly good chocolate dessert, I was also concerned about preserving my front-row seat and avoiding flying debris.

It was a difficult balancing act.

David and I exchanged a glance.

The kind married couples develop after years together.

An entire conversation without a single word.

Should we leave?

Absolutely not.

We picked up our dessert forks and continued watching.

At that point, we were emotionally invested.

Besides, it seemed rude to leave before the conclusion.

Beyond the Resort

We didn’t spend the entire week observing resort guests and wondering what spectacle might unfold next.

Mornings were often spent on the golf course, with afternoons reserved for exploring the island.

The concierge booked us on a rainforest excursion that involved bouncing through the island in a 4×4 before hiking to a waterfall hidden beneath the jungle canopy.

We wandered through local villages, traced the curve of the coastline, and discovered that Tobago’s real magic wasn’t in the resort, but in the people, the beaches, the rainforest, and the unhurried rhythm that shaped everyday life.

That exploration led me back to the beach for a horseback ride.

My guide, Michael, was calm and friendly — the kind of steady presence that seemed woven throughout the island.

It was booked as a group ride but ended up being just the two of us. We started with a bareback walk along the shoreline before easing into the warm Caribbean water.

My horse’s name was Mango, a name she’d earned from her obsession with the fruit. Evidently, she pulled mangoes straight from the tree behind her pasture. She also loved bananas — peel and all — which seemed perfectly suited to her personality.

Mango moved through the water with easy confidence, even as we ventured into deeper blue where the horses could swim. Her rhythm was steady, unbothered, almost meditative.

For an hour, the island stopped feeling chaotic.

No unexpected spectacles.

Just a horse, a quiet guide, warm water, and a stretch of Caribbean coastline.

Finally, Tobago showed me its softer side.

Alice, We Need to Talk

We flew home on New Year’s Day.

As our plane lifted off from Tobago, I found myself thinking about sweet, old Alice.

In Barbados, she enthusiastically recommended her three favorite Caribbean islands.

Barbados had given me a pharmaceutical taxi and a machete-wielding fruit vendor.

Tobago had turned out to be a front-row seat to an international soap opera.

I was beginning to wonder about Alice.

I couldn’t decide whether she was oblivious to the chaos around her, or simply so accustomed to Caribbean madness, that none of it seemed noteworthy.

Either way, I realized that Alice had left out a few key details.

Part of the Riding on Vacation Series

Barbados — The Beach Ride and the Pharmaceutical Taxi

On By jeanieelizabethIn Riding on VacationLeave a comment
View overlooking the Sandy Cove at Coconut Creek Hotel

Barbados was a long-standing bucket-list island, so we finally booked a stay at Coconut Creek in St. James, a small cliff-top hotel on Barbados’ west coast.

A staircase wound down to the beach below, where sailboats rested on the sand waiting for the day’s first drift into the calm Caribbean water.

The hotel had a cricket-themed bar—a reminder that in Barbados, cricket wasn’t just a sport. It was part of the culture.

It was at Coconut Creek that we met a lovely woman named Alice. Every summer, she left Britain behind and went island-hopping through Barbados, Tobago, and Antigua.

Alice spoke about the islands with the confidence of someone who had explored the Caribbean for years. She described each one in detail, carefully explaining their differences and charms. More importantly, she made it clear that these weren’t simply places she enjoyed visiting—they were, in her opinion, the three best islands in the Caribbean.

At the time, we listened politely and tucked her recommendations away.

The Beach

The sandy cove had its own rhythm — warm sand and the fading footprints of early morning beach walks.

The Cricket Club

Cricket was everywhere in Barbados, so it wasn’t surprising that Coconut Creek had its own Cricketeers Bar.

One afternoon, while enjoying a Red Stripe, David struck up a conversation with Kevin, the bartender, about cricket. It quickly became apparent that he knew far more than the average tourist.

When Kevin learned about David’s cricket accomplishments in Wales, his eyes widened. He immediately reached across the bar to shake his hand and promptly served him another Red Stripe.

In Barbados, that was apparently the cricket equivalent of being recognized by royalty.

A small pair of trophy bats still hang on my wall. They remind me of the athlete David was, and the path he never got to finish.

Life changes direction in ways we never expect. An illness ended his professional cricket career, but he went on to earn his PhD in Physics.

A single moment can change everything you once took for granted.

The Beach Ride

Every island we visited had its own personality, and Barbados was no different.

We booked a beach trail ride with a local stable and took a taxi across the island.

The guide was an American named Chuck, and I was paired with a palomino named Nugget.

The ride itself was incredible—a beautiful stretch of deserted beach where the horses walked through the sand and surf at a relaxed pace.

Everything about it felt peaceful and sun-washed, the kind of experience that makes you wonder why you don’t simply stay in the islands forever.

After the ride, Chuck offered us a ride back to the hotel.

I climbed into his car still floating somewhere between beach bliss and heat exhaustion when I noticed pills.

Everywhere.

In the cup holders.

On the floorboards.

Rolling across the console during turns like loose change.

The vehicle looked less like transportation and more like a pharmaceutical scavenger hunt.

Eventually, curiosity got the better of David seated in the back seat.

“What are all these pills?” He asked.

Chuck never blinked.

“Uppers, downers … help yourself.”

I considered this generous offer for exactly one second.

“Yeah, that’s going to be a hard pass.”

He offered no further explanation.

We asked no further questions.

We simply continued toward the hotel while assorted mystery tablets migrated around the car like tiny tourists.

Machete Dude

Barbados seemed determined to keep me slightly on edge.

When I got out of Chuck’s vehicle, I made the mistake of stopping to photograph a colorful roadside fruit cart.

I captured one quick photo, but the vendor turned just as I was about to snap a second shot.

Before I could lower the camera, he waved the machete and began enthusiastically explaining—with dramatic hand gestures—that photographs apparently required payment.

At that point, I decided the fruit cart no longer needed documenting.

I consider that one of my better travel decisions.

Island Treasures

I always looked for unique art while traveling through the Caribbean, and Barbados did not disappoint.

I wandered into a small studio filled with beautiful hand‑dyed batiks, each one more vibrant than the last.

I purchased three batiks, and this colorful fish still hangs on my wall today — a little burst of island color that never lost its magic.


The Island and I had Words

Barbados was lovely.

The beaches were beautiful. The people were welcoming. 

But everywhere I turned, some new form of chaos seemed to be waiting.

At some point, I concluded that Barbados and I simply weren’t in sync.

The island was trying very hard to provide a relaxing Caribbean vacation.

The Final Verdict: Barbados failed to make the repeat list.

We mutually agreed to give it a few years and see other people.

Part of the Riding on Vacation Series


Swimming with Horses in Palma Sola Bay… Anna Maria Island

On By jeanieelizabethIn Riding on VacationLeave a comment
📷: Ava Schultz Photography

I retired my personal horse, Rosie, from strenuous riding in her early twenties. An abused rescue, she had earned an early retirement package.

I would still hop on her bareback for a slow wander around the property, but I no longer “rode” her — not in the walk‑trot‑canter, trail‑miles sense of the word. To me, that defines riding.

What we did in her later years was simply keep each other company. Rosie was perfectly content in retirement; her only real complaint in Florida was the relentless swarm of flies who seemed personally offended by her existence.

Like most of my friends with senior horses, I shifted to riding rentals — the natural extension of staying in the saddle while honoring the limits of a horse who had already given so much.

So when I happened upon Florida Beach Horses on social media, I knew this would be my next riding adventure. 

I spent the night in Lakewood Ranch and drove to the meet location the next morning with the kind of nervous excitement that usually means you’re about to do something memorable.

As I crossed the causeway into Anna Maria Island, I spotted the horses hitched under a shade tree, tails flicking lazily in the warm air.

I parked in a sandy pull-off, checked in, and was paired with Buddy — mildly irritated, fully opinionated, but tolerant because he loved his job.

The Sand & Surf Ride began along the shoreline, each horse and rider moving in quiet formation. The bay lay still as glass, the sun already spilling gold across the water, while Buddy carried me forward with the calm certainty of a familiar task.

📷: Ava Schultz Photography

Back at the start, the saddles came off for the surf portion. The water was chest‑deep and the guides easily walked the horses out to a sandbar where we formed a circle. One by one, we stood on our horses’ backs, the bay glittering around us.

Then came the skiing.

📷: Ava Schultz Photography

We slipped into the water and grabbed hold of the horse’s tails as the guides mounted up.  A reminder floated back to secure my suit, though there was no real concern —only trust, and the strangeness of what was about to happen.

And then Buddy moved.

A surge and suddenly I was being drawn through the bay like a thread through silk—four hooves carving motion through water, turning effort into flight.

Next came swimming on horseback, in water just deep enough for the horses to lift into that slow, powerful float. They knew their job and followed the lead horse willingly. You don’t fall off a horse riding bareback in water — the buoyancy keeps you right where you need to be.

The final stretch was a race to shore. As we approached the shallows, Buddy started blowing bubbles like a mischievous child. It made me smile. His ears were pinned so I couldn’t tell if he was pleased the swim was over—or quietly disappointed it had to end.

📷: Ava Schultz Photography

The sun was shining. The water was warm and salty. It was the kind of day that doesn’t feel real until it becomes memory.

My next hiking and riding trips were to the Appalachian Mountains, Assateague, and Monument Valley, but those were unfortunately canceled due to unforeseen circumstances.

There are no guarantees in life, only moments —all we can do is enjoy the ride we’re on.

📷: Ava Schultz Photography

After the ride, I continued across the causeway still thinking about Buddy — the steady rhythm of his stride through the water.  It was a feeling — a quiet confidence a rider earns from a new experience.

I pulled straight into the parking lot at Holmes Beach and settled on the outdoor patio of Anna Maria Beach Café with fish tacos and an iced tea.  

Holmes Beach has soft, powdery white sand and shallow, turquoise waters. The beach spans seven acres of dunes, palms, and sea grapes. 

One unexpected thing I noticed on Anna Maria Island — and eventually became slightly obsessed with — was the island’s apparent competition for most entertaining mailbox.

Not normal mailboxes.
AMI mailboxes.

Dolphins leaping from posts.
Manatees the size of small kayaks.
Flamingos balancing beside driveways like permanent lawn guests.

Some looked hand-painted. Others looked like full art projects someone absolutely took too seriously in the best possible way.

At some point I realized the mailboxes were quietly telling the story of the island itself — playful, sun-faded, slightly eccentric, and completely unconcerned with being fashionable.

I started photographing them the way other people photograph sunsets.

Because on Anna Maria Island, apparently even the mailboxes have beach personalities.

Dinner was at the Sandbar Restaurant known for its toes-in-sand dining and sweeping gulf views. 

I was intrigued by The Doctor’s Office, a clever restaurant and bar in Holmes Beach.  I decided to stop in for a glass of recovery — a virgin Hibiscus Pom Margarita.

The bartender referred to my order as a ‘placebo’.  This is one of the most entertaining restaurant concepts on the island. The menu reads like a medical chart written by someone with a sense of humor: Culinary Prescriptions, First Aid, Initial Consultations, Taco Therapy, and Emergency Care.

The interior was eclectic — part vintage doctor’s office, part moody cocktail bar.  There was an eye chart on a ledge and a skeleton with a pink stethoscope propped in a corner, looking like he’d stayed for one drink too many.

Shopping on the island feels the same way — relaxed, local, and diverse — with little boutiques scattered throughout Anna Maria Island and along Bridge Street, where wandering around somehow becomes part of the entertainment.

Outside one boutique, exuberant parrots greeted me with a full‑volume chorus of chatter and whistles — tiny, feathered chatterboxes gossiping like they were on their third mimosa and absolutely living for the drama. 

That’s part of AMI’s charm.

Not flashy. Not manufactured. Just beach bars, quirky restaurants, bicycles leaning against fences, and a community that collectively decided life works better in sandals.

Apparently the cure for an ordinary week involves one beach horse, fish tacos, mailbox flamingos, and a prescription for Taco Therapy.

Part of the Riding on Vacation Series