The festivals worth planning a trip around. Dates follow their traditional pattern; confirm the exact days before booking travel.
Reggae Sumfest is the world's biggest reggae festival: a week of concerts in Montego Bay climaxing in two nights at Catherine Hall, with the biggest names in reggae and dancehall. It has run since 1993 and remains the genre's annual summit.
The main nights sell out; book Montego Bay accommodation early. The week also brings sound-system clashes, beach parties and street dances across the city.
Junkanoo is the Bahamas' great street parade: thousands of costumed revellers, goatskin drums, cowbells and whistles dancing through Bay Street from 2am on Boxing Day and New Year's Day. The costumes, built over months from crepe paper and cardboard, are works of art.
The groups (the Saxons, the Valley Boys, the Fancy Dancers) compete fiercely. Arrive early for a spot on Bay Street; the parade runs until morning.
Dominican Carnival is the Caribbean's most devilish: the diablos cojuelos (limping devils) of La Vega, in horned masks and mirror-covered costumes, parade every February Sunday, whipping vejigas (inflated bladders). La Vega's carnival is the oldest and wildest; Santo Domingo's Malecón hosts the national finale.
The masks are the art: papier-mâché demons in red, black and gold. February is high season; book the north and the capital early.
The San Sebastián Street Festival is Puerto Rico's biggest popular party: four days when Old San Juan's streets fill with hundreds of thousands of people, artisan stalls, live music on every plaza, and the cabezudos (big-headed puppets) parading. It honours Saint Sebastian, the city's patron.
It started in the 1950s as a neighbourhood fundraiser and is now the island's defining January event. Book Old San Juan accommodation months ahead; the crowds are enormous and joyful.
Crop Over is Barbados' harvest festival turned national carnival: six weeks of calypso, soca and rum climaxing in Grand Kadooment Day, the costumed street parade on the first Monday in August. It began in the 18th century as the sugar cane harvest celebration.
The season runs on soca: fetes every weekend, the calypso monarch competition, and the Bridgetown Market street fair. The final parade route runs along the Spring Garden Highway.
The Havana Jazz Festival (Jazz Plaza) is Cuba's premier music festival: founded in 1978 by Bobby Carcassés, it brings Cuban masters and international guests to theatres, clubs and open-air stages across Havana. Chucho Valdés, the festival's longtime president, usually plays.
Venues range from the Teatro Nacional to small Vedado clubs. January is Havana's best weather month; the festival is the best week of it.
Jamaica Carnival is the island's soca-and-dancehall answer to Trinidad: a week of fetes, J'ouvert and the Road March through Kingston, when thousands of costumed masqueraders dance behind music trucks. The modern carnival dates to 1989; the bands (Xodus, GenXS, Yard Mas) are now Caribbean-famous.
Road March Sunday is the main parade day, usually mid-April. Book Kingston accommodation early; the fetes sell out and the city fills.
The National Family Island Regatta is the Bahamas' oldest sailing race: since 1954, traditional wooden Bahamian sloops have raced in Elizabeth Harbour at George Town, Exuma, crewed by Bahamians with long pry boards for ballast. It is heritage as much as sport.
The races run over four days in late April, with Junkanoo performances, food fairs and parties ashore each evening. Anchor in Elizabeth Harbour for a front-row seat.
The Festival del Merengue is the Dominican Republic's national-dance blowout: two weeks of free concerts, dance displays and parades on Santo Domingo's Malecón, celebrating the merengue tradition that dates to the 19th century. The top merengue bands all play.
It runs from late July into early August, around the city's founding anniversary. The Malecón becomes a pedestrian party zone; hotels in Gazcue and the Colonial Zone put you in the middle of it.
Carnaval Ponceño is Puerto Rico's oldest carnival, documented since 1858: a pre-Lenten week of parades, music and dancing in Ponce's historic downtown, starring the vejigantes, the horned, brightly painted folkloric demons with their inflated vejigas.
It runs in the days leading up to Ash Wednesday, usually mid-February, closing with the Burial of the Sardine. The vejigante masks are folk art; the parades are free and participatory.
The Carnival of Santiago de Cuba is Cuba's biggest and most traditional: a late-July explosion of congas, comparsas and floats rooted in the 17th-century feast of Santiago Apóstol (July 25), fused with Afro-Cuban street culture and the July 26 national holiday.
The neighbourhood congas (Los Hoyos, San Agustín) parade with the Chinese cornet's unmistakable wail. Book Santiago accommodation months ahead: carnival week is the most-booked week in Cuban tourism.
The Oistins Fish Festival is Barbados' largest community festival: every Easter weekend, the fishing village of Oistins celebrates its fishing heritage with fish-boning contests, boat races, the greasy pole, craft stalls, soca and reggae, and the famous Friday fish fry supersized.
It has run since 1977. Easter is high season in Barbados; book the south coast early and arrive hungry.