- Fiestas de la Calle San Sebastián, January
- Carnival, Trinidad, February
- Jacmel Carnival, Haiti February
- Reggae Sumfest, July
- Crop-Over Festival, July
New Year’s is celebrated with huge gusto in the Caribbean. Resorts are full, and people are partying. Weather across the region is balmy, although there is the odd cool day in the north.
Triumph of the Revolution
Cuba celebrates the New Year, the revolution and the nation’s birth. Sure there are speeches – often long ones – but this is really an excuse for people to take to the streets with a passion.
Festival San Sebastián
Puerto Rico’s famous street party, Fiestas de la Calle San Sebastián, draws big crowds to Old San Juan for a week in mid-January. There are parades, dancing and much more.
Día de los Reyes
Across Puerto Rico, Día de los Reyes on 6 January toasts the three kings and is the high of a two-month-long extravaganza of Christmas celebrations. Many towns have festivals in their plazas,
Carnival is a huge event in many Caribbean countries, where it is tied to the Lenten calendar. No country has a bigger Carnival than Trinidad, which prepares all year for its exuberant explosion.
Bob Marley Birthday Bash
The love for the sound that plays in beach bars worldwide brings fans to the Bob Marley Museum in Jamaica on Bob Marley’s birthday, February 6, and kicks off Jamaica's reggae month.
Master of the Ocean
Called a ‘triathlon of the waves,’ this thrilling competition has the world’s best windsurfers, kitesurfers and surfers going board to board on Playa Encuentro in the Dominican Republic during the last week in February.
A week of celebration, the Holetown Festival marks the anniversary of the first English settlers’ arrival on Barbados.
Republic of Fun
The Dominican Republic celebrates its Carnival with great fervor every Sunday in February, culminating in a huge blowout in Santo Domingo on the last weekend of the month or the first weekend of March. Santiago hosts an international careta (mask) competition.
St-Barth’s five-day Carnival includes costumes, street dancing and a grand finale at Shell Beach.
Martinique’s Carnival Buzz
Fort-de-France, Martinique, explodes with Carnival energy in the five days running up to Ash Wednesday.
Party Puerto Rico
Ponce’s Carnival festivities are some of the best on Puerto Rico and are a chance to see traditional masks, music and lots of drunken parades.
Parading in Dominica
Dominica’s Carnival takes over Roseau for two days leading up to Ash Wednesday, with a costume parade among its highlights.
ABCs of Carnival
Jacmel in Haiti is known for its fantastic papier-mâché masks, which are made for the wild street theater for one of the Caribbean's best Carnivals.
It’s the biggest party in the Caribbean. Trinidad spends all year gearing up for its legendary, pre-Lent street party, with steel-pan bands, blasting soca and calypso music, and outrageous costumes. Ecstatic revelers indulge their most hedonistic inclinations as they welcome in Carnival.
Lovers of the golden-brown cane spirit shouldn’t miss this festival of drink, food and culture, which draws rum producers from across the Caribbean and Latin America to Nassau’s Fort Charlotte.
It’s high season throughout the Caribbean. On Barbados, American college students invade for spring break. The late-winter influx of visitors is greeted by lovely weather everywhere.
St Patrick’s Week
It’s not a day, it’s a week on Montserrat. There’s a lot of Irish heritage here so the day o’ green has always been huge. Costumes, food, drink, dance and concerts by the much-lauded Emerald Community Singers are highlights.
In March and April, thousands of American college students descend on Montego Bay in Jamaica for all-day, all-night bacchanalia. Other huge destinations are St Thomas in the US Virgin Islands and San Juan.
At this Anguilla music festival, reggae greats gather for late-night jam sessions.
Maricao Coffee Festival
Puerto Rico's annual Maricao Coffee Festival has demonstrations of traditional coffee-making and local crafting. The mountain backdrop is sublime, and the air fills with the scent of roasting beans.
Easter signals more Carnivals. High season continues but the winds of change are blowing. Rates begin to fall at resorts. Temperatures are climbing in the south but the Caribbean is mostly dry.
Bonaire’s harvest festival is held in the small town of Rincon in early April. This is only proper as Rincon was the historic home of the slaves who were brought to the island to make salt and harvest food. The celebrations include traditional dance and food.
Antigua Sailing Week
The Caribbean’s largest regatta, Antigua Sailing Week follows the Antigua Classic Yacht Regatta and involves a range of sailing and social events around Nelson’s Dockyard and Falmouth Harbour.
The Grenadines may be the most boat-friendly region in the Caribbean, with natural moorings throughout. And Bequia is the star of the Grenadines so it makes sense that St Vincent & the Grenadine’s top sailing event is here.
Curaçao’s ‘Feast of the Harvest’ features parades replete with folk music and dancing on Easter Monday. People in rural areas go a little nuts, and for them it outclasses Carnival.
Oistins Fish Festival
On the southern coast of Barbados, the Oistins Fish Festival commemorates the signing of the Charter of Barbados and celebrates the skills of local fishermen. It’s held over Easter weekend and features boat races, fish-filleting competitions, local foods and dancing.
The Easter Carnival in Kingston brings people into the streets for music and an impressive costume parade (www.jamaicacarnival.com). Huge, as you'd expect.
The two-week Sint Maarten Carnival, on the Dutch side, outclasses its counterpart on the French side. Activities begin in the second week after Easter.
Family Island Regatta
This regatta draws hundreds of yachts to Elizabeth Harbour, in the Bahamas, during the last week of April.
Carriacou Maroon & String Band Festival
Held late in the month, this music festival draws hordes of partiers from Grenada for big-drum music and dancing, string bands, Shakespeare Mas, and every other Carriacou tradition at venues around the tiny island.
Tobago Goat Racing
Easter means goat racing in Tobago, when the seaside stands in Buccoo are packed with spectators taking in the uproarious spectacle of thoroughbred goats and their on-foot ‘jockeys’ dashing for the finish line.
May sees the last of the Caribbean's carnivals, as the temperatures start to get hotter and hotter.
Cayman Islands' answer to Carnival is a week-long festival of music and masquerade parades – for adults and children alike – during the first week in May.
June remains dry and relatively storm-free. Like May, it’s not a peak time for visitors, except the savvy ones who value dry, sunny days and low hotel rates.
St Kitts Music Festival
Top-name calypso, soca, reggae, salsa, jazz and gospel performers from throughout the Caribbean pack into Basseterre’s Warner Park during this three-day music festival. Reserve a room way in advance.
A busy month! Summer holiday crowds start arriving, as do the very first tropical storms of the hurricane season. There’s another tranche of Carnivals and other special events.
Beginning in mid-July and running until early August, the Crop-Over Festival is Barbados’ top event and features fairs, activities and a parade.
The big mama of all reggae and dancehall festivals, held in late July in Montego Bay Jamaica, this event brings top acts together for an unforgettable party. Even if you’re not attending, you’re attending – the festivities tend to take over MoBay.
St Lucia Carnival
St Lucia’s biggest show takes place in Castries.
St Vincent’s Carnival and biggest cultural event for the year, Vincy Mas, is held in late June and early July.
Saba Summer Festival
Saba’s Summer Festival runs for one activity-filled week in late July.
Sint Eustatius celebrates for 10 days in late July, with music and local food.
Santiago de Cuba throws Cuba’s oldest, biggest and wildest celebration in the last week of July.
Santo Domingo Merengue Festival
Santo Domingo hosts the Dominican Republic’s largest and most raucous merengue festival. For two weeks at the end of July and the beginning of August, the world’s top merengue bands play for the world’s best merengue dancers all over the city.
BVI Emancipation Festival
Held on Tortola, the nation’s premier cultural event features beauty pageants, horse racing and ‘rise and shine tramps’ (3am parades led by reggae bands). The celebration marks the end of slavery (1834).
The summer high season continues and you can expect the first real storms of the hurricane season, although mostly that means heavy rains as opposed to big blows.
Anguilla Summer Festival
Anguilla’s 10-day-long Summer Festival takes place around the first week of August and is celebrated with boat races, music, dancing and more.
Grenada’s big annual event may be later than most islands’ but that doesn’t dim its festivities. The celebration is spirited and includes calypso and steel-pan competitions, costumed revelers, pageants and a big, grand-finale jump-up (nighttime street party).
The famous Antigua Carnival celebrates the country's emancipation from slavery during 10 days of merriment starting in late July, culminating with a grand parade on the first Tuesday in August. Calypso music, steel bands, masked merrymakers, floats and street parties all add to the excitement.
Crowds are down and the weather tends to be wet. This is the low season and it might be a good time to rent a beach house for a month and write that book.
Martinique Heritage Days
Martinique’s Journées du Patrimoine (Heritage Days) celebrate local culture and history principally through the opening of buildings to the public that are normally closed.
Dominica comes to the rescue of what is otherwise a quiet month (other than a few passing squalls). Some family-run businesses close for the month.
World Creole Music Festival
Dominica’s ode to Creole music attracts big-name Caribbean music and dance acts, and food vendors sell much spicy goodness.
Sea & Learn
For two weeks in October Saba becomes a learning center for scientists and enthusiasts who take part in activities from helping out on a shark research project to learning how to use tropical plants to make medicinal teas.
Hurricane season has mostly blown itself out and Christmas decorations are going up. Baseball season arrives in the Dominican Republic.
Livin in the Sun
Some of the hottest DJs from around the planet hit the decks at locations across Anguilla and out on Sandy Island during this three-day beat-filled festival in mid-November (www.livininthesun.com).
Ceremonies are held on November 16 to commemorate the date in 1776 that Sint Eustatius became the first foreign land to salute the US flag after the revolution.
Route du Rhum
It only happens every four years (next up: 2018) but the Route du Rhum sailing race (St-Malo to Pointe-à-Pitre; www.routedurhum.com) is a huge deal on the island of Guadeloupe. Book rooms a year or more in advance and prepare for one long party.
This wildly popular family-friendly extravaganza on Grand Cayman features a mock pirate invasion, music, dances, costumes, games and controlled mayhem. Book hotels in advance or you’ll be out on your booty.
St Kitts Carnival
Carnival is the biggest event on St Kitts. It starts in mid-November, kicking into high gear for two weeks of music, dancing and steel pan on December 26.
High season begins mid month and incoming flights are full. Rates are up and everything is open. Down backstreets Carnival prep is reaching fever pitch on many islands.
The Bahamas national festival starts in the twilight hours of Boxing Day (December 26). It’s a frenzied party with marching ‘shacks,’ colorful costumes and music. Crowds prepare much of the year for this Carnival-like happening.
Foxy’s New Year’s Eve Party
Hundreds of boats show up in Jost Van Dyke’s harbors on December 31. Every beach bar at this end of the British Virgin Islands is hopping.
A three-day gathering near Negril, Jamaica celebrating the best of Rastafari culture, from reggae and I-tal food to the Ganjamaica grower's cup (the latter sponsored by the Jamaican Ministry of Tourism).
No matter which Caribbean island you land on, you’ll quickly discover one thing: everybody loves to party. Any time of year, come rain or shine, you’ll find plenty of live music, dancing in the streets and countless reasons to celebrate.
Preparing for the Caribbean’s biggest street party is a year-long affair in Trinidad. Steel-pan and calypso competitions, elaborate costumes, mud-covered revelers, and blasting soca music.
Junkanoo, the Bahamas
A frenzied party of dance, music and colorful costumes rolls into Nassau on Boxing Day (December 26). This is the Bahamas’ high-energy national festival, where many marchers compete fiercely to put on the best performance.
Crop-Over Festival, Barbados
This big festival in Barbados marks the end of the sugarcane harvest. Over three weeks, beginning in mid-July, there are calypso competitions, fairs and more, finishing with a costume parade and fireworks on Kadooment Day in August.
Pirates Week, Grand Cayman
What with the pirate craze that’s swept the US, this extravaganza on Grand Cayman inspires many a trip south. Mock battles, planks that get walked and a booty of bad pirate jokes are among the pleasures.
Reggae Sumfest, Jamaica
Reggae and Dancehall fans alike gather in Montego Bay for Jamaica’s top reggae festival, held in July.