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.

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.

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.

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.

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