Naniki Music Festival (mid-Jan). Three days spanning jazz, R&B, reggae, and more, in the hills of Surinam, Barbados.
△ Havana International Jazz Festival (mid-Jan). Jazz aficionados flock for nine days of performances by music legends.
DISCOVER A Year in the Caribbean
△ Trinidad Carnival (last week). Fanciful costumes highlight this week of sensual festivities known as the biggest street party on earth. Port of Spain, Trinidad.
DISCOVER A Year in the Caribbean
St. Thomas International Regatta (late-Mar). Three days of world-class competition and shoreside excitement. St. Thomas, Virgin Islands.
△ Festival Casals (mid-Mar). Classical music festival in honor of founder and classical musician Pablo Casals. San Juan, Puerto Rico.
DISCOVER A Year in the Caribbean
△ Antigua Sailing Week (last week). Serious sailors compete in this prestigious week-long event known for equally serious partying.
Rara Festival (Easter week). Voudou-infused carnival parades highlighted by trumpet-like bamboo instruments and flamboyantly painted celebrants. Jacmel, Haiti.
DISCOVER A Year in the Caribbean
△ Dia de los Trabajadores (1 May). Half-a-million people flood through Plaza de la Revolución for Workers’ Day. Havana, Cuba.
Saint Lucia Jazz & Arts Festival (first half of May). The Caribbean’s premier jazz festival draws top international artists for two weeks of performances. Saint Lucia.
DISCOVER A Year in the Caribbean
△ Pineapple Festival (early Jun). All things pineapple, from cooking contests to plaiting the pineapple pole, provide a good excuse to party. Gregory Town, Eleuthera, The Bahamas.
DISCOVER A Year in the Caribbean
△ Reggae Sumfest (mid-Jul). A six-night line-up of iconic reggae performers starts and ends with a beach party like no other. Montego Bay, Jamaica.
DISCOVER A Year in the Caribbean
Carriacou Regatta (first week). Four days of sailing competitions and live entertainment. Grenada.
△ Crop-Over Festival (June-Aug). A six-week revelry, marking the end of sugar cane harvest, ending in carnival. Georgetown, Barbados.
DISCOVER A Year in the Caribbean
△ Caribbean Sea Jazz Festival (mid-Sep). Oranjestad pulsates to cool funk, soul, and jazz by maestros from George Benson to Chaka Khan. Aruba.
DISCOVER A Year in the Caribbean
△ World Creole Music Festival (last week). World-class Caribbean and international performers celebrate their music over three days and nights. Dominica.
Dominican Republic Jazz Festival (last weekend). Jazz legends such as Chuck Mangione and David Sánchez are regulars at this jazzfest. Dominican Republic.
DISCOVER A Year in the Caribbean
△ Pirates Week (first two weeks). Light-hearted revelry as locals and visitors make like Jack Sparrow with mock invasions, costume contests, and fireworks. Cayman Islands.
DISCOVER A Year in the Caribbean
Junkanoo (last week). The Bahamas’ most cacophonous street extravaganza includes a carnival parade led by flamboyantly adorned dance troupes. Nassau, The Bahamas.
△ Parrandas de Remedios (last week). Spectacular home-made fireworks highlight this bombastic carnival pitting two sides of town against one another. Remedios, Cuba.