8 January: Barbados Music Awards, Barbados
For such a relatively small player on the world stage, Barbados can boast a huge musical legacy, and these annual awards honour that talent. This is where Rihanna made her debut in 2006, and Livvi Franc and Shontelle have also played at the ceremony. As well as the red carpet, A-list celebrities and limousines, the event also gives members of the public the opportunity to see these artists perform under one roof.
• Check it out at: www.iticketsbarbados.com
 
25 January - 8 February: Blues Fest, St Vinvent & The Grenadines
Enjoy some cool sounds from St Vincent and The Grenadines as the seventeenth Mustique Blues Fest takes centre stage. The festival always begins with a sunset performance – a perfect event for families to gather and enjoy some great music at the legendary Basil’s Bar. Last year’s line-up included London blues legend Dana Gillespie and Grammy Award winner Joe Louis Walker.
• www.basilsbar.com

2 - 7 February: Caribbean Baseball Series, Dominican Republic
Catch some top-class baseball from the Dominican Republic as teams from the winter leagues of Mexico, Venezuela, Puerto Rico and the host nation compete at the Quisqueya Stadium. The first event was held in 1949 and it’s a great chance for the stars of the future to get noticed by the topAmerican teams, as the event is screened in the USA. 
• www.godominicanrepublic.com
 
26 February: The Annual Hare & Tortoise Swim, Antigua
Get some exercise, have some fun and raise money for a good cause by taking part in the annual Hare & Tortoise Swim organised by ‘The Anchorage’, English harbour since 2007. This exciting competition is for all ages from eight to 80 and covers a distance of approx 3/4 mile from Catamaran Marina to Pigeon Beach. For safety, Antigua & Barbuda Search & Rescue, Antigua Yacht Club Monitors & lifeguards are in attendance, and every year, trophies & prizes are presented to 1st & 2nd place in the 13 categories: All funds raised go to a great local charity – last year this was the St John Hospice for the care of the terminally ill in Antigua.

23 - 25 March: International Rolex Regatta, St Thomas
The International Rolex Regatta has been hosted by St Thomas Yacht Club since 1974 and is regarded as the jewel in the crown of the Caribbean spring regattas. Last year more than 700 sailors in 77 teams battled it out on Pillsbury Sound, completing distance courses that explored the local cays and islands. There are loads of great vantage points for interested spectators and the musical entertainment is fun too!
• www.rolexcupregatta.com

Plus... more important dates not to miss!
January (date TBA)
Le Marin Fair, Martinique
January 1
New Year’s Day Parade, St Kitts and Nevis
January 1
New Year’s Day and Parade, Antigua
January 2
Carnival Last Lap Parade, St Kitts and Nevis
January 6
Three Kings Day, St Croix, US Virgin Islands
January 16-22
Open Squash Championship, Barbados
January 18
Martin Luther King Jr. Day, US Virgin Islands
January 21
Errol Barrow Day, Barbados
January 21
Mount Gay Round Barbados Race, Barbados
January 25-29
Spice Island Billfish Tournament, Grenada
January 26-29
Bequia Music Festival, St Vincent and The Grenadines
January 27-31
Port Louis Sailing Festival, Grenada
February (date TBA)
Water Island Classical Music Festival, St Thomas, US Virgin Islands
February 7
Independence Day, Grenada
February 11
Antigua Valentine’s Sailing Festival, Antigua
February 14
Annual Celebration of Love, St John, US Virgin Islands
February 12-19
Holetown Festival, Barbados
February 18
Mardi Croix Parade, St Croix
February 19-24
Procigar Festival, Dominican Republic
February 20-21
The Real Mas, Dominica
February 24-26
South Grenada Regatta, Grenada
February 24-26
Tobago Carnival Regatta, Tobago
February 25
Hare and Tortoise Swim, Antigua
March (date TBA)
St John Blues Festival, St John, US Virgin Islands March (various dates), La Vega Carnival, Dominican Republic
March 1-4
St Maarten Regatta, St Maarten
March 10
Punta Cana Carnival, Dominican Republic
March 17-23
Holders Opera Season, Barbados
March 26-April 1
BVI Spring Regatta, Tortola, British Virgin Islands