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How to Carnival, Anguilla Style

It’s no secret the Caribbean knows how to party; anyone who frequents the Notting Hill carnival can clarify it’s an infectious weekend. Nothing however beats the mind-blowing experience that is the real thing, which I discovered firsthand this summer in Anguilla.

The Anguilla Summer Festival is 18 days of beach, boats and bacchanal, with a vibrant schedule of live music, boat racings, pageants and parades under the Caribbean sun. Occurring on the island for a quarter of a century to celebrate Anguilla’s emancipation, its roots are found in the decades of old traditional August Monday fairs, Bazaars and the old time Christmas festivities, which features many African influenced cultural expressions of island life. The Anguilla Summer Festival Committee aims to revive traditional art forms and blend with the modern to create a cultural extravaganza; they certainly seem to be doing something right…

Boat Racing

While there are over two weeks of festivities, the culmination of events takes place on August Monday, the first Monday of the month, which officially as a celebration in 1940 with the island’s national sport, boat racing. Two of the most pristine beaches, Sandy Ground and Meads Bay, are packed with spectators, binoculars glued to their faces, while trying to get through traffic on any kind of high ground which is nigh on impossible as everyone on the island jostles for a view of their favourite teams.


An undoubtable highlight of the Anguilla Summer Festival, J’Ouvert Monday capitalises on the talent of local musicians and artists to create the ultimate street jam. Starting pre-dawn, in the darkness of the capital The Valley at 4.30am, revellers start to gather, ready to march through the island all the way to the beachfront town of Sandy Ground. A parade of trucks are stacked with 10 metre high sound systems, live bands, DJs and MCs, creating the start of 24 hours of soca music street jams, beach parties and raves.

The fun doesn’t stop when you reach the beach however, as Sandy Ground is transformed from a tranquil tropical paradise to a full on party, with boats from across the Caribbean lined up and the water thronging with visitors ready to party. A huge beachfront stage provides ample entertainment and the air is thick with smoke from the dozens of beach barbecues, offering up freshly grilled crayfish and racks of juicy ribs, washed down with plenty of rum punch. This is is a day of serious partying.

Eyes Wide Shut

If J’Ouvert wasn’t quite enough, Eyes Wide Shut is the ultimate day break fête. Kicking off at 1am and finishing at 11am, this live music one-nighter attracts partygoers from all across the Caribbean. Visiting for a pre-breakfast session at 7am (bolstered by a rum punch of course…), we caught the headliner Machel Montano – a soca artist from Trinidad – who drew crowds from as far afield as Dominica, St Kitts & Nevis, Jamaica and Barbados as well as neighbouring St Maarten. Watching the sun come up over a field of confetti-strewn Caribbean revellers puts even Glastonbury in the shade.

The Pageants

Of course, it wouldn’t be the season without a pageant or two. The Miss Anguilla Pageant and bathing suit competition, Prince & Princess Pageant Jr. & Senior calypso Ms. Talented Teen, all take part throughout the festival, with the crowned winners taking pride of place at the very head of the Grand Parade of Troupes, the biggest event in the Summer Festival Calendar.

The Grand Parade of Troupes

The culmination of the summer’s festivities, this visual spectacular, sees troupes from all over the island come together on the last Friday of the Summer Festival to parade through the streets of The Valley. Costumes are nothing short of spectacular, painstakingly handmade by local creators and bedecked with jewels and feathers, dripping in embellishments. Flamboyant is the only word to describe this, with each troupe taking on a different theme, as ear-splitting sound systems take to the streets ahead of their dancers to ignite the senses.

It’s one of the most incredible ways to experience Anguillian culture (the Anguilla Tourist Board invited us to take part in their troupe for this year’s carnival). With a handmade costume created to my measurements, I took to the streets with the troupe under blistering 35 degree sunshine, loaded up with my camera and a drinks bottle filled with ice cold rum punch; somewhat helpfully, a refreshments truck behind our troupe ensured everyone stayed hydrated (albeit with more rum than water…) throughout the day. Hours of parading ensued, and while it was a long – and loud – day, it was an experience I will never forget.

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