Anguilla Summer Festival – Boats, Beaches and Bacchanal!

Anguilla Summer Festival is the most anticipated event of the year! A ten day Caribbean Carnival with boat races, costumes, parades, parties and live music.

August 1st, 2019

August 11th, 2019

Days to start

What is carnival in Anguilla?

anguilla summer festival

Anguilla Summer Festival is the biggest holiday on the island and is even more celebrated and beloved then Christmas! Anguilla’s Summer Festival is a cultural extravaganza and this year will celebrate a 45 year tradition of boats, bacchanal and beach parties that engulf the island every summer!

The Anguilla Summer Festival is a typical Caribbean emancipation celebration. Its roots are in decades of African influenced old traditional Monday fairs, Bazars and old time Christmas festivities, which features many cultural expressions of island life.

Anguilla Summer Festival is a typical reflection of contemporary Caribbean Carnivals. By day the celebrations are filled with beach parties, boat racing, concerts and dancing in the street. The nights are filled with parties, concerts and a whole extravaganza of carnival activities!

When Is The Anguilla Summer Festival?

The Anguilla Summer Festival is always held annually around the first Monday in August which is known as August Monday or Emancipation Day. The 2019 Anguilla Carnival will take place from August 1st -11th, 2019. Pre-carnival activities and the beginning of the Anguilla Summer Festival will start as early as July 14th, 2019.

Beaches, Boats, & Bacchanal! ✅ #AnguillaSummerFestival is the most anticipated event of the year in #Anguilla! Don’t miss this unique ⭐ #CaribbeanCarnival Click To Tweet

Where is Anguilla Summer Festival?

Anguilla, which means Eel, is a British overseas territory located in the Caribbean. It’s one of the most northerly of the Leeward Islands in the Lesser Antilles, sitting east of Puerto Rico and the Virgin Islands and north of Saint Martin.

Sandy Ground and Meads Bay are also where a lot of the carnival activities like the boat races and beach parties. Other carnival activities like the parades will be held in the Valley which is the capital of Anguilla and located in the middle of the island and home to approximately 600 of the island’s residents reside.

What is the difference between Anguilla Carnival and Anguilla Summer Festival?

anguilla summer festival

Carnival in Anguilla is also called Anguilla Summer Festival. Anguilla Summer Festival is more of a collective name that encompasses all summer pre-carnival events that kick off in in early July with and run until the end of summer. Anguilla Carnival the first Monday in August, which is celebrated as Emancipation Day!

What is the History of Anguilla Summer Festival?

The first August Monday celebration occurred back in 1940. It started as a boat race and continued to evolve over the years into one of the biggest beach parties in the region. Anguillans’ love for Boat racing developed from their natural love and dependence of the sea for basic survival.

Anguilla was a failed plantation for the early British settlers due to the almost desert terrain. The very early settlement mission was abandoned for more fertile lands like St Croix, BVI and Cancun. This turned Anguilla into a strange and unique colonial sociological situation absent of chattel slavery that was common on the other Caribbean islands.

The high frequency of droughts in Anguilla forced the locals to have an intimate dependence on the sea to subsidize for what the land didn’t offer. The failed plantation economy and severe economic conditions forced the Anguillan men to seek employment in the prosperous overseas cane fields.

They depended on the sea for their livelihood and their voyages across to the Dominican Republic is where the skill of Boat racing and art of boat building developed. Every time they would depart to and from Santo Domingo, soon turned into a fiercely contested race.

How to they celebrate Anguilla Summer Festival?

anguilla carnival

The Anguilla Summer Festival is celebrated with boats, beach parties and bacchanal. Some of the highlights of carnival are the boatraces, J’ouvert, Grand Parade of the Troupes, kiddies’ parade, Miss Anguilla Pageant and bathing suit competition.

There is also lots of live music shows and competitions like the the Soca and Reggae Night and the Leeward Islands Calypso Monarch competition. As well as the Prince & Princess Pageant Jr. & Senior calypso competition and Ms. Talented Teen. There is plenty of revelry and merrymaking, delicious local food and drinks, and the rum is free flowing.

2019 Anguilla Pre- Carnival Events

2019 Anguilla Summer Festival Schedule

anguilla carnival

Anguilla Boat Race Season

Boat racing is Anguilla’s lifeblood and national sport. Unlike most of the Caribbean islands where cricket is the main national sport, boat racing in Anguilla is higher in popularity than cricket as the favourite national pastime.

May through August is Boat Race season in Anguilla! It is a gripping display of sailing skills that most islanders have a keen interest in because every single village has its own boat and team to support. The sport evolved from when Anguillans had to find work on other islands and would race each other home on working schooners.

During the Anguilla Summer Festival, boat racing is a key part of the carnival action. The Anguilla Round the IslandBoat Race is one of the biggest spectacles in the Anguilla. The Boat races test the stamina of the competitors and even the spectators. Numerous party boats follow the distinctive sailing boats as they tackle the gruelling course, battling out for the win. 

Two of the islands most pristine and tranquil beaches Meads Bay and Sandy Ground are the main venues for the Boat races. Thousands of boat racing fans and enthusiasts come out to watch the races which are accompanied by lots of live music, food and drinks.

Boat races are held in three categories A, B & C. The Class A is the most popular boat races and are done on larger crafts – 28ft in length and can hold 14. These boats are open hulled and are probably the only open hull traditional sailboat around.

Anguilla Carnival – August Monday

August Monday is always the first Monday of August the biggest day of Anguilla Carnival. All other events that occur during the Anguilla Summer Festival line-up is planned around August Monday. It is the focus of Anguilla Carnival. August Monday is a full day which begins at 5am where thousands start celebrating.

The main attraction on August Monday is the famous “August Monday Boatrace” which begins at 1pm. When the race is over, the party doesn’t stop there it continues on until 1 am the next morning! So it begins at 5am Monday and continues until 1am Tuesday morning! It’s a big day plan on taking a few naps on the beach throughout the day to keep your energy high!

J’ouvert – Anguilla’s Biggest Party!

anguilla summer festival

For those not familiar with Caribbean Carnival, J’ouvert is a morning parade that begins before daybreak and is the traditional opening act for most Caribbean Carnivals. In Anguilla it’s one of the highlights of carnival season more so than the costumes parades. It is a showcase for local artists and musicians who compete for title of “Road March Champion”.

Kicking off around 5am, around 9000 revellers gather together in the pre-dawn darkness to begin a six hour march from The Valley, to the beachfront of Sandy Ground. Along the way there is loads of drinking, dancing and non-stop soca tunes. Everyone is invited to join in the fun! There nine judges who crown the Road March Champion and the winning band gets an $8000 price.

Once the road march reaches their destination the fun continues! The party continues on with live music from local and international bands performing for over 12 hours. Party boats are docked along the shore line and the beach is filled with people drinking, dancing, swimming and lots of merrymaking!

August Monday Boat Race

The main attraction on August Monday is the famous August Monday Boatrace! It begins from Sandy Ground at 1PM. The boats must race around the island, and it lasts most of the afternoon. The first races are just qualifying ones to determine which boats will compete in the Champion of Champions Race which is held on the final Sunday of Carnival week. 

Anguillans are very passionate about the August Monday boatraces! Because the majority of Anguillans will have a boat that they are associated with. Everyone follows the race closely! Many will even track the boats from land with their cars and binoculars in hand. You can also hop on a party boat which follow the race from the sea.

When the race is over the party still continues on! The party on the beach continues on until the early morning. So August Monday is one full day! Especially for those that begin their party at 5am and continue on for almost 24 hours straight!

August Tuesday & August Wednesday

anguilla summer festival

The next day there is another boatrace as well as a Seafood Festival in Island Harbour that starts at 10AM until evening hours. It is often called a mini-Festival del Mar. There are three bands that will play throughout the day, and the most delicious fresh seafood BBQs taking place all over the island. In the evening is the senior Calypso Competition which is a hugely popular carnival event!

On Wednesday afternoon, is another boat race takes place at Blowing Point which also counts towards the Champion of Champions race. In the evening is the Miss Anguilla Queens Pageant it is one of the more anticipated shows on the stage during Carnival week. The pageant includes a costume and swimsuit competition which is to show strength of self, in a competitive environment.

August Thursday

For those sailors who are disappointed with their Wednesday race results, they don’t have to fear because on August Thursday is the Meads Bay boatrace. Meads Bay is the place to be on this day and while the boatrace sets off there are loads of food trucks set up around the island as well as lots of live music.

Another highlight of the Anguilla Summer Festival is the daybreak fete – Eyes Wide Shut, which is an early morning beach party that takes place at Sandy Ground and features leading local and international artists.

August Friday – Parade of the Troupes

anguilla summer festival

Friday is another highly anticipated carnival day and certainly the most colourful day of carnival! Anguilla which is known as the Rainbow City becomes even more colourful today! It’s the second and final Road March called The Parade of Troupes. Beginning at midday it is a fun event for the whole family! Anyone is welcome to watch and even join in on the dancing.

It is a flamboyant, vibrant and colourful celebration as the troupes dance through The Valley streets. The troupes are made up of different villages around the island of Anguilla and they make the streets come alive with music, colour and dance! The troupes are also judged on their costumes, their performance, and colour and overall best troupe is selected!

The Anguilla Tourist Board has created a series of incredible costumes, that were inspired by the theme ‘Rainbow City’, whose cascading hues aim to reflect the Anguillan culture, people, experiences, flora and fauna.

The different pillars of the “Rainbow City” experience are depicted through the 3 Anguillan sections – Spellbound, Hanami and Enchanted. Spellbound reflects the Anguillan Spirt.  Hanami affirms the pride and strength the Anguillan people. Enchanted signifies the power, strength and royalty of the Rainbow people!

August Saturday

On Saturday is the Poker Run, which is an all-day event that attracts up to 100 boats, who make four stops at Da Vida’s, Island Harbour, Rendezvous Bay and Meads Bay. Each stop features a different beach party, loads of games, competitions, music, food, drinks, dance contests. The winning poker hand receives $5000.

On Saturday night the Leeward Island Calypso Competition is held at the Landsome Bowl. Calypso is a huge part of Anguillan culture, so don’t miss this final competition!

August Sunday – The Champions of Champions Boat Race

The very last day of Carnival is when the Champion of Champions boatrace final is held. The winner from each race during carnival week will compete in this final to find out who will become the official Champion of Champions! Sandy Ground is packed with avid boat lovers and it is a fabulous closing to the Anguilla Summer Festival! 

On Sunday, Sandy Ground is sure to be packed with people one last time for the year. Yet, it is more peaceful than August Monday, and a nice end to the Anguilla Summer Festival. After carnival is over, then the island of Anguilla returns to its serene, quiet self!

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How to get to Anguilla?

Getting to Anguilla is very easy! Most guests choose to fly to St. Maarten – SXM Princess Juliana International Airport, and then arrive in Anguilla via sea-shuttle, ferry or air transfer. This is actually the easiest and most direct way to get there. While Anguilla has an airport AXA its more expensive to fly their directly and the ferry only takes 20 minutes, which is faster than waiting at airport.

Several US cities have a direct flight to St. Maarten and there are even direct flights to SXM from Paris and Amsterdam. The only places with direct flights to Anguilla are from Puerto Rico, St Barts and St. Maarten. The flight from St. Maarten to Anguilla only takes 10 minutes, leaves 3 times a day and costs about $100. While it isn’t the quickest or most convenient way, it will certainly offer some breathtaking views!

Check out flight costs here.

Where to stay in Anguilla?

This is a hard question to answer because in Anguilla there is no good side or bad side to the island! It just depends on what you are looking for from your vacation. The West End is the more resort like part of the island.

The East End is less developed and more relaxed. Many of the high end restaurants are located in the West End or Sandy Ground (mid-island) area. All over Anguilla are stunning beaches. The more popular ones are Rendezvous Bay, Shoal Bay and Meads Bay.

Check out some accommodation options here.

How to get around in Anguilla?

Anguilla is only 16 miles long and 3 miles wide, so it is actually pretty easy to get around. There is only the one main road which runs the entire length of the island and takes approximately 30 minutes to drive from one end to the other. There are numerous smaller roads that lead off the main road to provide easier access to different beaches, villages, coves and attractions.

There is no public transport in Anguilla because of its small size there simply isn’t a need. Getting around Anguilla by car is the most popular method of transport and cars can easily be rented. You can also get a taxis, bike or even just walk around the island. As Anguilla is governed by British law be aware that you must drive on the left! The speed limit on the island is 30mph making driving a pretty relaxing experience, and there is no need to rush.

Renting a car will give you the freedom to explore the island at your own pace and discover different beaches along the way. If you rent a car in Anguilla you will need to have a valid driving licence as well as purchase a temporary Anguilla licence. This licence costs $20 USD and is available for purchase through most car rental companies.

Check out car rental costs here.

What to do and see in Anguilla?

anguilla carnival

Anguilla is a sliver of paradise! The shape of the island is what inspired its name which derives from the Spanish word for eel! Anguilla has 33 pristine beaches with gorgeous white sand and crystal blue sea. Anguilla is said to be super authentic as the locals won’t sell their soul to tourism. Cruise ships are kept away and you won’t see an open-top bus in sight.

Savvy travellers love to visit Anguilla during this time of year because not only will they get to experience balmy sea breezes, calm waters and great weather but also during carnival they can just be immersed in all the local cultural events.

Anguilla is known as the ‘Wreck Diving Capital of the Caribbean’ because there are nine shipwrecks that were deliberately sunk in the surrounding waters. So scuba diving and snorkelling is a must do! While there isn’t to much to explore in The Valley, its close to lots of landmarks like Copper Hole (large blow hole),  The Dolphin Lagoon at Meads Bay, The Old Fort at Sandy Hill and Pitch Apple Hole (prehistoric cave).

There are so many fabulous places to eat in Anguilla, where Caribbean flavours have been combined with American and European to create new interesting flavours, in fact the Eel is said to be “the culinary capital of the Caribbean.”

For more information about tours, things to do, sightseeing tours, day trips and more click here.

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