Poker Run 2026 Anguilla: The Caribbean's Ultimate Adrenaline-Fueled Boat Party

The coral-fringed paradise of Anguilla sets sail for its most thrilling boating event as the Poker Run 2026 takes over the island's coastline on Saturday, August 8, 2026, at 9:00 AM, during the 52nd Anguilla Summer Festival (Carnival & Boat Racing). This one-day adrenaline-fueled adventure is one of the island's most exciting boating events, where participants hop between famous beaches, beach clubs, and coastal stops around Anguilla, collecting poker cards at each location while enjoying pop-up poker games, spectacular boat views, DJ entertainment, local food, rum punches, and friendly competition against the stunning backdrop of Anguilla's turquoise waters and white-sand beaches. The event kicks off bright and early in Sandy Ground, beach hops to David's Beach Club in Crocus Bay, Leons and Meads Bay, and concludes with a massive raft-up party at Little Bay, where boats anchor in a huge circle for the ultimate end-of-day celebration with prize giveaways and final poker card draws.

The 2026 Anguilla Summer Festival runs from Friday, July 10 to Sunday, August 9, 2026, with the Poker Run serving as a beloved staple of the festival that brings together boaters, beach lovers, and party-goers for one of the Caribbean's most exciting boating events. The event features pop-up poker games at every stop, with participants collecting cards number three, five, and the final card before the big prize giveaways. Whether you're a seasoned boater, a beach enthusiast, or just here for the party, the Anguilla Poker Run is an unforgettable experience that showcases the island's maritime culture, celebration spirit, and year-round Caribbean bacchanal.

"The Anguilla Poker Run is an unforgettable experience that showcases the island's maritime culture, celebration spirit, and year-round Caribbean bacchanal."

Anguilla's Premier Boating Adventure

The Poker Run in Anguilla is a one-day boating event that combines speed, competition, and party atmosphere into one unforgettable island experience. Participants start at Sandy Ground, beach hop around the island collecting poker cards at each stop, and join in epic contests while enjoying pop-up poker games, amazing local food and drinks, DJ entertainment, and friendly competition all while soaking up the stunning views of Anguilla's coastline.

• Date: Saturday, August 8, 2026 (one-day event)
• Start Time: 9:00 AM at Beaches and Coastlines of Anguilla
• Location: Beaches and Coastlines of Anguilla (multiple beach stops)
• Starting Point: Sandy Ground (8:30 AM registration, 10:00 AM departure)
• Festival: 52nd Anguilla Summer Festival (Carnival & Boat Racing)
• Festival Period: July 10 to August 9, 2026 (month-long celebration)
• Stops: Sandy Ground, David's Beach Club (Crocus Bay), Leons and Meads Bay, Little Bay (raft-up finale)
• Activities: Pop-up poker games, beach contests, DJ entertainment, food and rum punches, prize giveaways
• Ending: Raft-up party at Little Bay with final poker game and big prize giveaways

August 8: Beach Hopping & Poker Action

The 2026 Anguilla Poker Run takes place on Saturday, August 8, 2026, with the day structured around multiple beach stops, poker card collections, contests, and a final raft-up celebration. The event kicks off at Sandy Ground at 8:30 AM with poker hand registration, wristband distribution, and participation flags, then departs at 10:00 AM sharp to begin the beach hop around the island.

Poker Run 2026 Schedule:

8:30 AM – 9:00 AM (Registration at Sandy Ground):

• 8:30 AM: Poker hand registration begins at Sandy Ground
• Wristbands: Distribution of participant wristbands
• Flags: Participation flags flying high
• Preparation: Boaters prepare for departure, crew members gather

10:00 AM (Departure from Sandy Ground):

• 10:00 AM: Event officially starts, boats depart Sandy Ground
• First Stop: Begin beach hopping around Anguilla's coastline

Stop One: David's Beach Club (Crocus Bay):

• Location: David's Beach Club in Crocus Bay
• Activity: Pull card number three while the crowd cheers on the legendary slip and slide
• Contests: Beach contests, slip and slide competition
• Food and Drinks: Local food, rum punches, and refreshments available

Stop Two and Three: Leons and Meads Bay:

• Location: Leons and Meads Bay
• Activity: Lunch, rum punches, and card number five
• Final Pop-Up Poker Game: The final pop-up poker game happens here before big prize giveaways
• DJ Entertainment: DJ music and beach party atmosphere

Final Stop: Little Bay (Raft-Up Party):

• Location: Little Bay
• Activity: Raft-up party, boats anchor in a huge circle
• Final Celebration: Ultimate end-of-day celebration
• Big Prize Giveaways: Final poker card draws and major prize awards
• Music: DJ entertainment continues through the celebration

New Feature for 2026:

New this year, pop-up poker games at every stop add an extra layer of excitement and competition to the event. Participants collect cards at each location, building their poker hand throughout the day, with the final card drawn at the raft-up party at Little Bay before the big prize giveaways.

Iconic Anguilla Locations

The Poker Run in Anguilla is structured around the island's most famous beaches and beach clubs, creating a route that showcases the stunning coastline and world-class hospitality of Anguilla. Each stop offers a unique experience, from legendary slip and slide contests to beach party atmospheres and massive raft-up celebrations.

The Four Key Stops:

1. Sandy Ground (Starting Point):

• Location: Western Anguilla, famous white-sand beach
• Role: Registration and departure point for the Poker Run
• Features: Crystal-clear waters, beach clubs, restaurants, bars
• Time: 8:30 AM registration, 10:00 AM departure
• Nearby: Sandy Ground Beach Club, Meads Bay (10 minutes), The Valley (15 minutes)

2. David's Beach Club (Crocus Bay):

• Location: Crocus Bay, northeastern Anguilla
• Role: First beach stop with card number three collection
• Features: Legendary slip and slide contest, beach party atmosphere
• Activities: Slip and slide competition, card drawing, local food, rum punches
• Nearby: Crocus Bay Beach, Island Harbour (15 minutes)

3. Leons and Meads Bay:

• Location: Meads Bay, western Anguilla
• Role: Second beach stop with lunch, rum punches, card number five
• Features: Luxury beach clubs, world-famous beach, sunset views
• Activities: Final pop-up poker game, lunch, DJ entertainment, beach party
• Nearby: Carimar Beach Club, Four Seasons Resort Anguilla, Shoal Bay East

4. Little Bay (Raft-Up Finale):

• Location: Little Bay, secluded beach in Anguilla
• Role: Final stop with raft-up party and big prize giveaways
• Features: Secluded beach, perfect for raft-up celebration
• Activities: Boats anchor in a huge circle, final poker card draw, prize awards, DJ music
• Nearby: Body Bay, secluded coastal areas

Why These Beaches Matter:

Each stop on the Poker Run represents one of Anguilla's most iconic beach locations, from the world-famous Sandy Ground to the luxury Meads Bay and the secluded Little Bay. The route showcases the island's diversity, from bustling beach clubs to quiet, secluded shores, giving participants a comprehensive tour of Anguilla's coastline.

The Anguilla Summer Festival

The 2026 Anguilla Summer Festival is the 52nd edition of Anguilla's most vibrant annual celebration, running from Friday, July 10 to Sunday, August 9, 2026, with the Poker Run serving as a beloved staple of the festival. The event sits right at the end of the festival calendar, on Saturday, August 8, 2026, just before the Champion of Champions Boat Race and Splash III on Sunday, August 9, 2026, which marks the festival's official closing ceremony.

2026 Festival Schedule Leading to Poker Run:

• July 10, 2026: Village-Rama (festival kickoff)
• July 11, 2026: Calypso Semi-Finals
• July 12, 2026: Miss Tiny Tott Pageant
• July 18, 2026: WASTED Cooler Festival
• July 26, 2026: Peter Perkins Boat Race / Miss Anguilla Pageant Part I
• July 29, 2026: Opening Night & Fireworks Display
• July 30, 2026: Jr. Calypso Monarch / Soca Monarch
• July 31, 2026: Wet Fete
• August 1, 2026: South Valley Community Street Festival / Band Clash / Ban-O-Rama
• August 2, 2026: Boat Race / Carnival at Leons / Prince & Princess Show
• August 3, 2026: J'ouvert Morning / Sir Emile Gumbs Boat Race / Caribbean Beach Party
• August 4, 2026: Boat Race / Miss Talented Teen Pageant
• August 5, 2026: Eyes Wide Shut / August Thursday / Beach Party & Boat Race / Senior Calypso Monarch
• August 6, 2026: Grand Parade of Troupes
• August 7, 2026: Constitution Day (public holiday)
• August 8, 2026: Poker Run / Leeward Islands Calypso Monarch
• August 9, 2026: Champion of Champions Boat Race / Splash III (11 AM - 5 PM, Sandy Ground)

The Poker Run is positioned as one of the festival's most anticipated events, drawing boaters, beach lovers, and party-goers from across the Caribbean and international markets. The festival attracts visitors who want to experience the island's culture, music, boat racing, and festive atmosphere all at once.

Travel Tips for Poker Run 2026

Getting to Anguilla:

• Anguilla (AXA) has no international airport; travelers must fly to Princess Juliana International Airport (SXM) in St. Maarten (15-minute flight or 30-minute ferry)
• Ferry services: Regular ferries from St. Maarten to Blowing Point Ferry Terminal in Anguilla
• Private flights: Seaplane and charter flights from St. Maarten to Wallblake Airport (AXA)
• Travel time: 15-minute flight or 30-minute ferry from St. Maarten

Where to Stay During Poker Run 2026:

Sandy Ground / Meads Bay area (closest to start and finish):

• Sandy Ground: Beachfront properties with easy access to Poker Run starting point
• Meads Bay: Luxury resorts including Carimar Beach Club and Four Seasons Resort Anguilla, 10 minutes from Sandy Ground
• The Valley: Capital town with budget and mid-range accommodations, 15 minutes from Sandy Ground

Other areas:

• Shoal Bay East: World-famous beach with luxury resorts, 20 minutes from Sandy Ground
• Crocus Bay: Near David's Beach Club, 15 minutes from Sandy Ground
• Body Bay: Secluded beach with boutique hotels, 15 minutes from Sandy Ground

Best Areas to Stay:

• Sandy Ground: Closest to Poker Run starting point, with beachfront properties and easy access to all stops
• Meads Bay: Luxury resorts with ocean views and 10-minute drive to Sandy Ground
• The Valley: Central location with capital town accommodations and easy island access

Practical Tips:

• Book accommodation early: August is peak festival season, and hotels fill quickly during the Poker Run
• Reserve boat spots early: If you plan to participate, book your boat or entry with organizers before the event
• Bring cash: Eastern Caribbean Dollars (XCD) and USD are both accepted; USD widely accepted
• Dress for the beach: Swimsuit, sunscreen, hat, sunglasses, and comfortable shoes are essential
• Stay hydrated: Tropical heat requires plenty of water, especially during outdoor beach events
• Plan for transportation: Rent a car or use taxis to get between beach stops if you're not on a boat
• Check registration times: Arrive at Sandy Ground by 8:30 AM for wristbands and registration
• Get travel insurance: Highly recommended to protect your investment in festival travel
• Join the party: Whether boater or spectator, the Poker Run is open to all participants and viewers

Anguilla Beyond the Poker Run

The Poker Run is just one of many reasons to visit Anguilla in July–August 2026. The coral island offers year-round attractions and activities:

• Grand Parade of Troupes: Saturday, August 7, 2026 (11:00 AM, The Valley Streets)
• Champion of Champions Boat Race: Sunday, August 9, 2026 (11:00 AM - 5:00 PM, Sandy Ground Beach)
• J'ouvert Morning Parade: August 3, 2026 (The Valley Streets to Sandy Ground Beach, 5:00 AM)
• Culturama Boat Races: August 2–7, 2026 (four days of thrilling boat races at Sandy Ground and Meads Bay)
• Festival Del Mar Anguilla: Biennial celebration of the sea with live music, swimming competitions, and boat races in Island Harbour
• Shoal Bay East: World-famous beach with powdery white sand and turquoise waters
• Meads Bay: Luxury beach with Carimar Beach Club and Four Seasons Resort
• Rendezvous Bay: Secluded beach with dramatic sunset views
• Scuba diving: World-class dive sites including coral reefs and shipwrecks
• Snorkeling: Protected marine areas with sea turtles and tropical fish

July and August are ideal times to visit Anguilla, with warm weather, fewer crowds than peak winter season, and the beginning of the optimal summer travel window for Caribbean island-hopping. The Poker Run adds a unique boating and party experience to any visit.

An Event That Defines Anguilla's Maritime Spirit

The Poker Run 2026 is one of Anguilla's most thrilling boating events and a beloved staple of the 52nd Anguilla Summer Festival (Carnival & Boat Racing), taking place on Saturday, August 8, 2026, at 9:00 AM, at the Beaches and Coastlines of Anguilla, with registration at Sandy Ground at 8:30 AM and departure at 10:00 AM sharp, marking one of the island's most adrenaline-fueled adventures that combines speed, competition, and party atmosphere into one unforgettable island experience. This one-day boating event features participants beach hopping around the island collecting poker cards at each stop, joining in epic contests while enjoying pop-up poker games, spectacular boat views, DJ entertainment, amazing local food and drinks, rum punches, and friendly competition all while soaking up the stunning views of Anguilla's coastline, with stops at David's Beach Club in Crocus Bay (card number three, slip and slide contest), Leons and Meads Bay (lunch, rum punches, card number five, final pop-up poker game), and a massive raft-up party at Little Bay (boats anchor in a huge circle for the ultimate end-of-day celebration with big prize giveaways and final poker card draws).

The event is described as one of the Caribbean's most exciting boating events, bringing together boaters, beach lovers, and party-goers for an adrenaline-fueled experience that showcases Anguilla's maritime culture, celebration spirit, and stunning coastline. Whether you're a seasoned boater, a beach enthusiast, or just here for the party, the Anguilla Poker Run is an unforgettable experience that combines speed, competition, fun, and excitement around the island. New this year, pop-up poker games at every stop add an extra layer of excitement and competition, with participants collecting cards number three, five, and the final card before the big prize giveaways at the raft-up party at Little Bay.

"Book your trip to Anguilla for August 8, 2026, to experience the ultimate Caribbean boating adventure."

Book your trip to Anguilla for August 8, 2026, to experience the ultimate Caribbean boating adventure. Arrive early for registration at Sandy Ground by 8:30 AM, join the beach hop to David's Beach Club, witness the legendary slip and slide contest, sample local Caribbean cuisine and rum punches, experience the DJ entertainment and beach party atmosphere, and celebrate at the raft-up party at Little Bay with big prize giveaways. The Poker Run sits right at the end of the Anguilla Summer Festival 2026 (July 10 to August 9), inviting you to be part of the island's most exciting boating event at the beaches and coastlines of Anguilla.

Frequently Asked Questions

When is the Poker Run 2026 in Anguilla?
The Poker Run 2026 takes place on Saturday, August 8, 2026, at 9:00 AM, during the 52nd Anguilla Summer Festival running from July 10 to August 9, 2026.

Where does the Poker Run 2026 take place?
The event takes place at the Beaches and Coastlines of Anguilla, with stops at Sandy Ground (starting point), David's Beach Club in Crocus Bay, Leons and Meads Bay, and Little Bay (raft-up finale).

What is the Poker Run in Anguilla?
The Poker Run is a one-day boating event where participants beach hop around the island collecting poker cards at each stop, joining in contests, pop-up poker games, DJ entertainment, food, rum punches, and friendly competition while enjoying Anguilla's stunning coastline.

How do I get to Anguilla for the Poker Run?
Fly to Princess Juliana International Airport (SXM) in St. Maarten, then take a 15-minute flight or 30-minute ferry to Anguilla. Ferry services run from St. Maarten to Blowing Point Ferry Terminal in Anguilla.

What should I bring to the Poker Run?
Bring swimwear, sunscreen, hat, sunglasses, comfortable shoes, cash (XCD or USD), water, and a camera. Arrive at Sandy Ground by 8:30 AM for registration and wristbands.

What is the raft-up party at Little Bay?
The raft-up party at Little Bay is the Poker Run's final stop, where boats anchor in a huge circle for the ultimate end-of-day celebration with the final pop-up poker game, big prize giveaways, and DJ entertainment.

Verified Information at a Glance

• Event: Poker Run 2026 Anguilla (Anguilla Summer Festival - Poker Run / Leeward Islands Calypso Monarch)
• Category: Boating Event / Beach Party / Poker Competition / Summer Festival Event / Maritime Adventure
• Date: Saturday, August 8, 2026 (one-day event)
• Start Time: 9:00 AM at Beaches and Coastlines of Anguilla
• Registration: 8:30 AM at Sandy Ground (poker hand registration, wristbands, flags)
• Departure: 10:00 AM sharp from Sandy Ground
• Location: Beaches and Coastlines of Anguilla (multiple beach stops)
• Festival: 52nd Anguilla Summer Festival (Carnival & Boat Racing)
• Festival Period: July 10 to August 9, 2026 (month-long celebration)
• Starting Point: Sandy Ground (western Anguilla, famous white-sand beach)
• Stop One: David's Beach Club in Crocus Bay (card number three, slip and slide contest)
• Stop Two and Three: Leons and Meads Bay (lunch, rum punches, card number five, final pop-up poker game)
• Final Stop: Little Bay (raft-up party, boats anchor in huge circle, big prize giveaways, final poker card)
• New Feature 2026: Pop-up poker games at every stop
• Activities: Pop-up poker games, beach contests, slip and slide, DJ entertainment, food, rum punches, prize giveaways, raft-up party
• Description: "One of the Caribbean's most exciting boating events"
• Gateway Airport: Princess Juliana International Airport (SXM), St. Maarten; 15-minute flight or 30-minute ferry to Anguilla
• Best Areas to Stay: Sandy Ground, Meads Bay, The Valley, Shoal Bay East
• Nearby Events 2026: Grand Parade of Troupes (August 7), Constitution Day (August 7), Champion of Champions Boat Race (August 9)