2018 Anguilla Summer Festival Winners

After all the preparation, excitement and hardwork, the Anguilla Summer Festival winners are seen waving to spectators atop floats during the Parade of Troupes.

To witness this, visitors and Anguillians living abroad make their way to Anguilla to experience a high caliber of performances ranging from music to boat racing and see who will come out victorious.

Anguilla Summer Festival competitions

  1. Miss Venus Model Caribbean
  2. Miss Tiny Tott Pageant
  3. Wet Fete
  4. FLOW Soca Rave
  5. Soca Bandclash/Bandorama
  6. ANGLEC Junior Calypso Competition
  7. ANGLEC Senior Calypso Competition
  8. Miss Sotiabank Talented Teen
  9. Miss Anguilla Pageant
  10. Parade of Troupes
  11. Leeward Islands Calypso Competition
  12. Champion of Champions Boat Race

* no Prince & Princess in 2017

*no Tiny Tott Pageant in 2018

2018 Anguilla Summer Festival Winners

FLOW Soca Rave – Shea Shea (Groovy Monarch) & Mr. Decent (Power Monarch)


Prince and Princess Show – Adrian T Hazell Primary School

Soca Bandclash & Bandorama – Infusion XL (Winner of Bandclash) & Synergy (Winner of Bandorama)

Synergy Bandclash Anguilla Summer Festival
Synergy at Bandclash/Bandorama 2018

Scotiabank Talented Teen – Charisma Jones-Chin

Calypso Competition – Mighty Linger (Junior Monarch) & Mighty Springer (Senior Monarch)

Mighty Linger Anguilla Calypso
Mighty Linger

Mighty Springer Anguilla Calypso
Mighty Springer

Miss Anguilla Pageant – Miss Mikeela Skellekie

Grand Parade of Troupes – Exodus HD (Road March) & Players Troupe (Best Troupe)

Players troupe Anguilla Summer Festival
Players Troupe

Leeward Islands Calypso Competition – Queen Thalia

Past Anguilla Summer Festival Winners

2017 Anguilla Summer Festival

Ms Venus Model Caribbean – Shakira Pitt | St Kitts & Nevis

A native of St. Kitts, Ms. Shakira Pitt, was crowned at the Miss Venus Model Caribbean.

**No image at this time

Miss Tiny Tott Pageant – Kyanee Rogers

Miss Tiny Tott
Photo: Keiroy Browne Photography

Little Miss Kyanee Rogers best known for her bravery, talent, charisma and her priceless reactions, received the Tiny Tott title for 2017-2018.

Wet Fete – Pantha Vibes International (PVI)

PVI took home the title for Best Wet Fete song once again. Winning with their song, Wet Again.

FLOW Soca Rave – Big Rash | Groovy & Power Soca King

Big Rash Soca Rave Winner Anguilla Summer Festival Winners

The first time contender, Big Rash, rose to the top for the FLOW Soca Rave (formerly Soca Monarch) – winning both categories, Groovy and Power Soca. Taking the double crown title from the 2016-2017 Soca Monarch, Mr. Decent.

Soca Bandclash & Bandorama + Soca Toss up – Infusion XL

Infusion XL Bandclash Winner Anguilla Summer Festival Winners

For a second time, the Infusion XL band has been able to achieve a ‘clean sweep’ of all judged segments for the annual Soca Bandclash & Bandorama. They definitely shook their tambourines in celebration.

Junior Calypso Competition – Super Mario

Super Mario Junior Calypso Winner Anguilla Summer Festival Winners

The young calypsonian, Super Mario, is no stranger to the stage or winning. He was crowned the Junior Calypsonian – taking the title from Kaiso Nikky who did not defend her crown.

ANGLEC Senior Calypso Competition – Roxxy

Roxxy Senior Calypso Winner Anguilla Summer Festival Winners

Competing for the second time, the talented Roxxy was successful in defending her crown with her songs “Who’s Gonna Carry On?” and “Recycling”.

Miss Scotiabank Talented Teen – Deztynee Bryan

Miss Scotiabank Winner Anguilla Summer Festival Winners

Miss Deztynee Bryan made history for the 2017 Miss Scotiabank Talented Teen. It is evident that she astonished the audience as well as the judges when she secured the title of Miss Scotiabank Talented Teen 2017-2018.

Remarkably, she won all judged segments which is a feat seldomly accomplished.

Miss Anguilla Pageant – Dee-Ann Kentish-Rogers

Dee-Ann Rogers Miss Anguilla Winner Anguilla Summer Festival Winners

The articulate, well poised, Dee-Ann Kentish-Rogers, was named Miss Anguilla 2017-2018 after high-calibre performances from all four contestants.

She also won the Best Swimwear and Best Cultural Wear segments.

Grand Parade of Troupes, Road March & Best Troupe – Infusion XL & Players Troupe

The 2017 Summer Festival has been very favourable for Infusion XL – every time you think about Infusion XL, you think “clean sweep”. They have been successful in beating the four-time Road March Champions, Exodus HD.

Infusion XL Road March Winner Anguilla Summer Festival Winners

The largest troupe, Players Troupe with their theme, ‘Malliouhana: A Turtle’s Paradise’, centralised on Anguilla and its turtle population, coloured the streets for the Grand Parade of Troupes while bringing awareness to the need to protect our turtle species.

Players Troupe Parade of Troupes Winner Anguilla Summer Festival Winners
Players Troupe Parade of Troupes Winner Anguilla Summer Festival Winners

21st Leeward Islands Calypso Competition – King Zacari | Antigua

No stranger to calypso or the Leeward Islands Calypso Competition in Anguilla, the Antiguan veteran calypsonian, King Zacari, dethroned the Calypso Monarch 2016-2017, Roxxy.

**No image at this time

Poker Run – Unexpected

Poker Run Winner Anguilla Summer Festival Winners

The Captain & Crew of the boat, Unexpected, won best hand in the Poker Run and received the Grand Prize of US$5000 + Best Dressed Crew, US$200.

Champion of Champions Boat Race

Blue Bird (Class A) & Kedro’s Pride (Class B)

**No image at this time

2016 Anguilla Summer Festival

Miss Venus Model Caribbean

Alsanarda Hanley | St Kitts & Nevis

Winners 2016 Miss Venus Model CaribbeanMiss Alsanarda Hanley, a native of St Kitts & Nevis, came out victorious in the 2016 Miss Venus Model Caribbean. A lover of the performing arts and an Art Teacher, Miss Hanley felt at home on stage even though she was miles away from it.

Miss Tiny Tott Pageant

Ailyn Tavarez

Winners Miss Tiny Tott

A ‘tiny tott’ with a huge performance, Miss Ailyn Tavarez rendered the audience speechless with her poise and ability to own the stage through speech (in English & Spanish), talent and modeling her Children’s Cultural Wear and Princess Evening Wear.

FLOW Soca Monarch

Mr Decent (Power & Groovy Soca)

The FLOW Soca Monarch Competition is judged in 2 categories – Power Soca & Groovy Soca. Mr Decent was able to capture the crown in both categories. View snippet of his performance. A very talented and experienced artist, Mr Decent is famously known for his performances at Smokey’s and Pumphouse with the Musical Brothers.

Soca Bandclash/Bandorama

Infusion XL

A photo posted by Cleaner Mann (@kylonhull) on

The rain poured that day, but the people came out to support their bands and their bands did play! Ultimately, Infusion XL won with their exhilarating performance – capturing the title for both competitions for the first time!

Prince & Princess Show

Adrian T Hazel Primary School | Jauron & Reba

Winners 2016 Prince & Princess

It’s always a big thing when your past primary school has a competition. It’s and even bigger thing when your child is in that competition. Jauron & Reba had the support of man fans of the school and their ability to perform and take the win ATHPS.

Junior Calypso

Kaiso Nikki, Nakia Webster

Winners Nikki
Photo credit: Rudy Webster

She has been singing for quite some time but she’s still a junior and her performance of “The Nation’s Cry” afforded her the opportunity to wear the crown.

Miss Scotiabank Talented Teen

Miss Arielle Gaskin

Winners 2016 Scotiabank Talented Teen
Photo credit: Rudy Webster

Miss Arielle Gaskin, one of four competent, beautiful and talented competitors, became the reigning Miss Scotiabank Talented Teen with originality and poise.

Anglec Calypso Monarch Competition

Roxxy, Roxanne Webster

Winners Roxxy Calypso

Though this was her first time competing in the senior competition, Singing Roxxy is far from a stranger on the calypso scene. Her stellar performance of her songs “All I See” and “Tax Paradise” and comfort among seasoned calypsonians from Anguilla lead her to victory.

Miss Anguilla Pageant

Miss Carencia Rouse

Miss Anguilla Carencia Rouse
Photo credit: Malik Richards

Though the competition was tight, Miss Carencia Rouse became the reigning Miss Anguilla 2016 -2017. Also one of 3 recipients of the 2016 Chevening Scholarship in Anguilla, she will be leaving the island to pursue a Master’s Degree.

Parade of Troupes

Road March & Best Troupe | Exodus HD & Majestic Gems

Exodus HD went ’round the corner, round the bend” and they couldn’t catch them again as they won their 4th consecutive road march after being judge for J’ouvert and Parade of Troupes.

Winners Circle 2016 Anguilla Summer Festival

Majestic Gems painted the streets with the colours of many Caribbean islands. This year’s theme, “Islands United” showcased the deep sense of comradery experienced during Anguilla carnival.

20th Annual Leeward Islands Calypso Competition

Roxxy, Roxanne Webster

A photo posted by Roxxy (@roxxymusic) on

Another first for Singing Roxxy, coming out winner against calypsonians from across the region.

Champion of Champions Boat Race


And boy did those boats race! A season riddled with poor weather conditions came to a beautiful end with Satellite taking home the win for both “Boat of the Year” and “Champ of Champs” – this is our National Sport; until next year.

Praises also to the Contestants & Organizers

Though we have singled out those who have been awarded the title of winners in the various competitions, we must take some time out to thank all those who put so much into competing.

Without their efforts, there would be no winners, no competition and ultimately no Anguilla Summer Festival for us all to look forward to.

Upcoming Anguilla Summer Festival Events

Coming to the Anguilla Summer Festival? Here’s your Anguilla Carnival Checklist.

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