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Anguilla: Event calendar for an alluring break


13 June, 2023


31 August, 2023


Moonsplash Music Festival: The Moonsplash Music Festival in Anguilla is a vibrant and captivating event that showcases a diverse line-up of local and international musicians. Held against the backdrop of the picturesque Anguilla island, attendees can immerse themselves in a celebration of music, culture, and the breathtaking Caribbean ambience.

Where: Rendezvous Bay, Anguilla

When: Annually, mid March

Anguilla Culinary Experience: The Anguilla Culinary Experience is a delectable journey for food enthusiasts, showcasing the island's vibrant culinary scene. Renowned chefs, both local and international, come together to create unforgettable gastronomic experiences, highlighting the flavours of Anguillian cuisine with a sprinkling of global influences.

Where: Anguilla

When: Annually, early May

Anguilla Day: An annual celebration of the Island's culture, heritage, and national pride. This festive occasion brings together locals and visitors alike for a day of vibrant parades, lively music, traditional dances, and delicious local cuisine. From colourful displays of Anguillian traditions to spirited festivities, Anguilla Day provides a joyful atmosphere that allows everyone to embrace and appreciate the island's rich history and cultural identity

Where: Anguilla

When: Annually, May 30th

Anguilla Summer Festival: An electrifying celebration of music, culture, and Caribbean traditions. This vibrant festival spans several days and features lively parades, colourful costumes, calypso music, soca performances, and exhilarating boat races. Visitors can immerse themselves in the vibrant atmosphere and experience the rich cultural heritage of Anguilla during this unforgettable summer extravaganza.

Where: Sandy Grounds & Meads Bay, Anguilla

When: Annually, early August

Anguilla Cup: The Anguilla Cup is a prestigious sailing regatta that takes place in the azure waters surrounding the captivating island of Anguilla. Sailors from around the world come together to compete in a series of exhilarating races, testing their skills against the beautiful Caribbean Sea. This thrilling event combines the excitement of sailing with the allure of Anguilla, creating an unforgettable experience for participants and spectators alike.

Where: Anguilla

When: Annually, early November

Villas in Anguilla with astounding views:

Villa Triton

From the breathtaking ocean views to its lavish and thoughtful architecture, Villa Triton is definitely a remarkable residence. Overlooking the glistening Caribbean Sea from an elevated vantage point on Little Harbour with the towering mountains of St Martin as a backdrop, you simply couldn't ask for a better view.

Where: Little Harbour, Anguilla

Round Rock Estate

Savour all Anguilla's splendour from the modern Round Rock Estate, situated in the picturesque Rendezvous Bay region, which offers a fantastic selection of beaches and facilities. At its forefront, a large heated swimming pool overlooks the glittering sea. Seating areas within the pool allow you to bathe in its warm waters while enjoying a refreshing cocktail.

Where: Rendezvous Bay, Anguilla

Ani Estate

Perched on the very edge of the land, Ani Estate is nestled amidst the rugged cliffs of Anguilla, surrounded on all sides by the glittering Caribbean Sea. Boasting total privacy and stunning panoramic views of the vast ever-changing horizon, Ani Estate is an island getaway like no other.

Where: Little Bay, Anguilla

The onefinestay experience

Here at onefinestay, we specialise in bespoke vacations. Whether you’re after relaxation, adventure or simply looking to discover the awe-inspiring beauty of Anguilla, we’ve prepared a selection of exclusive concierge services to ensure that your break is as memorable as it should be. From private chef hire to at-home spa experiences, you’ll be given these options when you book your stay with one of our Travel Advisors. Everything is taken care of before your arrival, so you can simply turn up and unwind!

Tempted by an alluring break to Anguilla?