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