Island Escapes with a Twist: Hidden Islands That Host Unique Sporting Events 

From Volcano Runs to Pony Swims: Wild Sports on Hidden Islands

Going for an island escape is not only about the turquoise waters and swimming with the sea turtles. It is also about going on an adventure, learning more about the local culture, and diving deeper into the island vibe. 

There are many islands all around the world that feel like paradise, with a mix of adrenaline, jaw-dropping scenery, and culture, far from the tourist traps we are used to on some of the commonly visited islands. 

So, if you are someone who wants to explore new things and is open to new ideas, maybe visiting an island with rich culture and unusual events is the perfect way to spice up your adventure. But how to know if an island has a unique culture?  

Well, you can always look at some of their most popular events throughout the year. These events perfectly highlight their culture, and it is something worth visiting if you want something new.  

This got us thinking, what are some of the hidden islands that host unique sporting events?

Orkney Islands' International Island Games

Okay, Scotland might not be the first thing that comes to mind when you think about tropical adventures, but for someone who wants something new and doesn’t mind the lack of warm weather and beaches, this is the perfect place to visit.

The Orkney Islands are a wonder of Viking history tucked in the rugged cliffs. But what’s so special about these islands?

Well, every two years, they host the International Island Games, which is a week-long festival where athletes from 24 island communities like Guernsey and Bermuda battle it out in 12 sports.

Yes, it’s like they have their own Olympic Games, anything from archery to triathlon. The good thing is that the 2025 edition is set for July this year, and they expect close to 2,000 competitors.

It is definitely something new and unexpected, from the location to the number of competitors and sports.

Chincoteague's Pony Swim Spectacle

Next, we go off Virginia’s coast to Chincoteague Island, which is famous for its wild ponies. Yes, the island is full of small and cute ponies. But how did they even get here? Well, historians tell us that they are descendants of shipwrecked Spanish horses.

So, what do you do when you have an island full of horses? Race them? - Well, they have other ideas.

How about a horse swimming competition? Yes, you’ve heard that right. Every July, they host the Chincoteague Pony Swim, where a herd of 150 ponies swim across the Assateague Channel to auction foals for the local fire department.

Just because this is a unique event, it draws many spectators every year. There are some reports that 40,000 spectators were watching this event last year (which is more than some horse racing events).

The good thing is that the competition (which horse finishes first) isn’t really important, as long as all of them make it across safely.

Bequia's Beach Horse Derby

Bequia, a tiny Caribbean jewel in St. Vincent and the Grenadines, is all turquoise bays and no stoplights. Every August, it hosts the Bequia Beach Horse Derby, a barefoot race along Friendship Bay, where local riders gallop retired Thoroughbreds on sand, dodging waves.

It is just like the Preakness Stakes, only on the beach and with less safety equipment. So, if you missed the Preakness Stakes results, maybe it is time to head over to Bequia and watch a beach horse race.

All you need to do is fly to St. Vincent, ferry to Bequia, and stay at Bequia Plantation Hotel. Pack flip-flops and a hat. This derby’s a salty, carefree sprint that screams Caribbean heart.

Pico Island's Volcano Trail Run

Pico, a volcanic speck in Portugal’s Azores, boasts the tallest peak in the country, Mount Pico. Every June, it hosts the Pico Volcano Trail Run, a 25km race across black lava fields and misty vineyards, a UNESCO World Heritage site.

Runners climb 1,000 meters, dodging volcanic rocks, with 300 participants in 2024, per event logs. The theme’s raw endurance, mirroring Pico’s rugged beauty.

Fly to Pico via Azores Airlines from Lisbon, book a stone cottage in Madalena, and pack trail shoes. Post-race, sip local wine and spot whales offshore. This run is for those who crave adventure with a side of island charm.

Saba's Stairway to Heaven Climb

Saba, a tiny volcanic dot in the Caribbean Netherlands, is nicknamed the “Unspoiled Queen” for its lush cliffs and quiet vibe. Every November, it hosts the Saba Stairway to Heaven, a race up 3,000 stone steps from the harbor to Mount Scenery’s peak, an 887-meter climb.

About 100 runners joined in 2024, gasping through rainforest trails with ocean views. The motive’s sheer grit, testing your legs and lungs.

Bequia's Easter Regatta

Bequia, a 7-square-mile gem in St. Vincent and the Grenadines, is a sailor’s haven with no traffic lights. Every Easter, it hosts the Bequia Regatta, a four-day sailing race where 50 yachts, from local sloops to sleek catamarans, compete around turquoise bays.

The 2024 event drew 1,000 spectators, with beach parties and calypso music. The motive’s nautical heritage, celebrating Bequia’s boat-building roots.

Fly to St. Vincent, then ferry to Bequia, and stay at a guesthouse like Gingerbread Hotel. Bring sunscreen and dance moves. This regatta’s a sun-soaked, salty blast that captures island life.