July 30th - Peter Perkings A Class Boat Race // Talented Teen Competition

Anguilla Summer Festival - Grand Parade of Troupes (sponsored by Motorworld)

The Grand Parade of Troupes is a signature event of the Anguilla Summer Festival. Motorworld confirmed as title sponsor (announced June…

August 3rd - Carnival Kick Off

Anguilla Summer Festival - Caribbean Beach Party

All-day beach party and concert at Sandy Ground Beach, starting at 12 PM. Features sun, sea, and sounds of the Caribbean. Follows…

Sir Emile Monday A Class (Sandy Ground)

Anguilla Summer Festival - Miss Talented Teen

Youth talent competition at Landsome Bowl Cultural Centre at 8:00 PM. Young performers showcase skills and creativity in a spirited…

Anguilla Summer Festival - Miss Anguilla Pageant: Crowning Glory

Miss Anguilla Pageant Part II at Landsome Bowl Cultural Centre at 8:00 PM. Five contestants compete for the title: Akema Carty,…

Boat Racing Watch Party — Season Closing Race

Anguilla Summer Festival - Eyes Wide Shut

The ultimate daybreak fete at Sandy Ground Field, starting at 1:00 AM. Celebrates into the morning hours with continuous music and…

Aug 7th - J'Ouvert // August Monday Boat Race & Beach Party

Aug 8th - A Class Boat Race // Miss Anguilla

Anguilla Summer Festival - Poker Run

A high-stakes adventure on the seas along the beaches and coastlines of Anguilla, starting at 9:00 AM. Features poker, fun, competition…

Aug 9th - A Class Boat Race // Senior Calypso Competition

Champion of Champs A & B Class (Sandy Ground)

Aug 11th - Grande Parade of Troupes

Aug 13th - Champion of Champion A & B Class Boat Race

The Anguilla Cup

International Tennis Federation-sanctioned event in November. Features world-class tennis, exhibition matches, junior and senior…

Special Movember Brunch

Rum Punch Sundays at Scilly Cay

Sunday Funday at Leon’s

Social Sundowners at Celeste Terrace

Taco Tuesday at Bar Soleil

Sprocka at Straw Hat

Tokyo Bay Asian Celebration

The Meads Bay BBQ

Vere Musiq at Sunset Lounge

Sexy Saturdays

The Anguillita Rum Journey

Mexican Fiesta at Breezes

DJ Sugar at Madeariman

Kick back on the sand and enjoy some "sweet beats." Join DJ Sugar for a relaxed evening of music and dining at one of Anguilla's…

12th Avenue Live at Sunset Lounge

Elevate your Sunday evening at the Four Seasons. Experience an unforgettable night with 12th Avenue, performing live against the…

Late Night with DJ Tights

Get ready to dance the night away! DJ Tights takes over Lit Lounge for a high-energy Sunday night session featuring special cocktails…

Live Jazz Night at Uchu

Experience luxury and melody at Belmond Cap Juluca. Enjoy a sophisticated Live Jazz Night at Uchu, paired with world-class service and a…

Vere Music at Sunset Lounge

Start your weekend with good vibes. Vere Music kicks off the weekend every Friday at Sunset Lounge with hit songs and great energy!

The Final Course: A 5-Course Murder Mystery at Savi Beach Club

Awaken your inner sleuth with an intriguing murder mystery and five-course dinner at Savi Beach Club on Meads Bay Beach. Professional…

Cape Air & NCBA Beach BBQ + Bartending & Chef Mystery Basket Battles

The grills will be hot and the drinks cold at the Cape Air & NCBA Beach BBQ + Bartending & Chef Basket Battles at the Anguilla Great…

An Evening at Karaya – Coastal Cocktails & Cuisine with Guest Chefs Oliver Poilevey, Sam Handwerger & Timothy Dean + Chef Carrie Bogar

Celebrate the start of ACE 2026 at seaside Karaya on Shoal Bay West. Savor substantial, Mediterranean-inspired passed hors d’oeuvres…

All Rum Leads to Rome – An Immersion in Roman Cuisine at Zemi Beach House

First you'll retreat to the sanctuary of Zemi Beach House’s artisanal bar, The Rhum Room, for a private tasting. Sip selected rare,…

Salt Chef’s Table Experience at Four Seasons Resort Anguilla

Join us for a captivating ten‑course Chef’s Table experience that traces the evolution of Anguillian cuisine from the island’s west to…

Wine-Pairing Dinner at Jacala with Grands Vins de France & Cyril Meuley of Boisset La Famille des Grands Vins

Chef Proprietor Alain Laurent of Jacala is partnering with Nathalie Le Sénéchal of Grands Vins de France Anguilla and Cyril Meuley of…

Sunset Champagne Catamaran Sail with Calypso Charters

TICKET SALES ARE NOW CLOSED FOR THIS EVENT Join Calypso Charters' experienced crew and your boat mates for an unforgettable sunset sail…