Every year in August, at the heart of the Anguilla Summer Festival, the Anguilla Poker Run brings the island to the rhythm of engines and music. More than just a nautical competition, this event symbolizes the passion of the people of Anguillais for the sea, unity and conviviality. Over the years, it has become a highlight of the summer season and a showcase for the local maritime heritage.
An original concept combining luck and sharing
The Anguilla Poker Run takes up the idea of the poker run popularized by bikers and yachtsmen: sail from one point to another, draw a card at each stop, and form the best possible hand.
In Anguilla, the spirit is different: speed doesn’t matter. Participants stop at each beach to take a break, share a meal, listen to music and chat. The randomness of the game mingles with human warmth, and each stopover becomes a party in its own right.
Year after year, the event attracts crews from Anguilla and neighboring islands such as Saint Kitts, Nevis, Antigua, Saint Martin, Saint Barthélemy, Tortola and Saint Thomas. The whole island rallies to welcome this day on the water, synonymous with friendship and shared passion.
Wendell "Bonty" Herbert, the face of the Anguilla Poker Run
Behind this adventure lies Wendell “Bonty” Herbert nicknamed Mr. Poker Run . Since 2016, he has led the organization of the event with the same energy and passion.
In an exclusive interview with Richès Karayib, he talks about the birth of the project:
“In 2016, a man was admiring my boat in Sandy Ground and said to me: why don’t you take part in the poker run in the Virgin Islands? I’d never heard of it.”
“I went home, watched the Leverick Bay Poker Run on YouTube, and I was bluffed. I thought, I can do something like that here.”
But in Anguilla, the concept has taken on a very special twist:
“Over there, they just collect the cards and leave. Here, I’ve changed the format: you draw your card, but you stay to celebrate, with contests and entertainment.”
The first edition brought together around thirty boats. Today, the event regularly attracts more than a hundred boats, proof of its growth and deep roots in local culture.
A history of resilience
Since its beginnings, Anguilla Poker Run has gone through many phases. Even during the pandemic, Wendell Herbert found a way to keep the tradition alive:
“During the COVID, when everything was closed, we were able to keep it, because we were at sea. We did it on the north coast, with no stopovers ashore.”
This determination illustrates the deep bond between the people of Anguilla and their marine environment.
Over time, the event has also spread throughout the region. Wendell Herbert launched a Poker Run in St. Kitts, in tribute to his parents who died at sea in 1994.
“I started in 2022, on Father’s Day.”
For him, this initiative is more than just a competition. It’s a way of honoring memory, creating links and passing on a legacy.
A highlight of the Anguilla Summer Festival
The Anguilla Summer Festival, also known as the Anguilla Summer Festivalis held every year between late July and mid-August. It’s the island’s biggest popular festival, featuring music, dance, boat races and cultural events. The Anguilla Poker Run takes pride of place, alongside traditional regattas, the Calypso Monarch and a parade of costumed troops.
The event usually takes place on the Saturday of the Festival devoted to nautical activities, often around August 9 or 10. The start takes place at Sandy Ground, the heart of Anguilla’s maritime life, where crews gather in the morning for the briefing and the first distribution of cards.
The route: a festive loop around the island
The circuit varies from one edition to the next, but follows the same spirit: sailing around the island, stopping off at several emblematic beaches. The most frequent stops are Crocus Bay (Da’Vida Beach Bar), Island Harbour, Rendezvous Bay and Meads Bay, sometimes with a fifth stop on Scrub Island when weather permits.
Each stop is an opportunity to enjoy a heavenly setting and a unique atmosphere. Local DJs provide the entertainment, while participants take time for refreshments and entertainment.
As Wendell Herbert sums it up: “Five stops, five beach parties.”
Safety and respect for the sea
Even if the day is all about fun, the organizers remind us each year of the strict rules: speed limits, respecting distances, zero waste, and compulsory safety equipment (life jackets, VHF radio, fire extinguishers). These measures are supervised in collaboration with the Royal Anguilla Police Force and local maritime authorities.
The event also has an educational dimension, raising awareness among young people and visitors alike of the importance of preserving the coastline and coral reefs, Anguilla’s true natural treasures.
A proud moment for the whole island
Today, the Anguilla Poker Run is much more than just a race. It’s a contemporary tradition that unites generations, attracts visitors and reinforces the sense of belonging to an island community united by the sea.
Each edition is a reminder of the extent to which Anguilla remains true to its identity: that of a proud island, open to other Caribbean territories, and deeply attached to its maritime heritage.
