Caribbean Entertainment Events for January 2026
- 1 hour ago
- 4 min read
January 2026 kicks off the Caribbean entertainment calendar with high-energy fetes, cultural festivals, live music, food experiences, and nature-driven adventures. From Jamaica’s all-white parties and reggae festivals to Trinidad’s Carnival warm-up events, plus international music and lifestyle festivals across Barbados, Curaçao, St. Barths, and the Dominican Republic, the region comes alive right from the first day of the year.
Whether you’re chasing dancehall vibes, soca fetes, reggae festivals, or immersive island experiences, here’s your ultimate guide to Caribbean entertainment events happening in January 2026.
Caribbean Entertainment Events for January 2026: Festivals, Fetes, Music & Culture Across the Islands
Jamaica: New Year’s Energy & Reggae Culture
SANDZ – All-White Edition
📅 January 1, 2026
📍 Stadium East, Kingston
One of Jamaica’s most anticipated New Year’s Day events, SANDZ delivers premium all-white aesthetics, top DJs, and nonstop dancehall and reggae energy.
Sunrise Day Soiree
📅 January 1, 2026
📍 Kingston, Jamaica
An early-morning New Year celebration blending music, fashion, and sunrise vibes for partygoers who want to start the year on a high note.
White & Briight Festival Jamaica
📅 Saturday, January 3, 2026 | 9:00 PM
📍 Jamaica National Stadium
A signature all-white festival experience combining music, fashion, and high-octane party energy.
Rich Lifestyle: Tropical Paradise – All-White Edition
📅 Friday, January 2, 2026 | 9:55 PM
📍 Sugarock Lagoon, Jamaica
An upscale tropical party experience set against scenic waterfront views, featuring premium vibes and fashionable crowds.
Rebel Salute Music Festival
📅 Saturday, January 17, 2026
📍 Plantation Cove, Jamaica
One of the Caribbean’s most respected reggae festivals, Rebel Salute celebrates roots reggae, Rastafarian culture, and conscious music.
Trinidad & Tobago: Carnival Season Begins
Junior Panorama Finals
📅 Sunday, January 18, 2026
📍 Trinidad and Tobago
A celebration of youth steelpan excellence, showcasing the next generation of Trinidad’s national instrument.
Soka in Moka 2026
📅 Sunday, January 4, 2026 | 6:00 PM
📍 Trinity College, Moka Estate Road
An all-inclusive Carnival fete featuring music by Johnny Q Sound Company, food, drinks, and premium soca vibes.
French Toast: Breakfast & Bacchanal Fete
📅 Sunday, January 4, 2026 | 6:00 AM
📍 Queen’s Hall, Port of Spain
A sunrise breakfast party blending Carnival energy with food, drinks, and early-morning bacchanal.
Mical Teja: MAS – The Experience
📅 Sunday, January 11, 2026 | 5:00 PM
📍 Queen’s Hall, Port of Spain
A cultural showcase highlighting Carnival rhythms, performance, and the artistry of Mical Teja.
CRUIZIN Down D Islands
📅 Saturday, January 24, 2026 | 8:30 AM
📍 Departs from various locations, Trinidad & Tobago
A daytime cruise event combining music, social vibes, and island scenery.
Booze & Bacchanal: The First Jam
📅 Saturday, January 24, 2026 | 10:00 AM
📍 St. James, Port of Spain
A high-energy Carnival jam known for lively crowds and nonstop soca.
Carnival Pop-Up – Night Market Edition
📅 Friday, January 30, 2026 | 3:00 PM
📍 Queen’s Hall, Port of Spain
🎟️ Free Entry
A vibrant marketplace featuring fete wear, jewelry, local products, and live music.
Jadel – Live Performance & WORK
📅 Friday, January 30, 2026 | 8:00 PM
📍 The Sound Forge, Port of Spain
A soca-powered live performance paired with the high-energy WORK event.
Cruise With The Saints
📅 Saturday, January 31, 2026 | 7:00 PM
📍 C3 Marina, Port of Spain
An evening cruise event combining music, drinks, and social vibes on the water.
Evolve 2026: Food & Drink Experience
📅 Saturday, January 31, 2026 | 6:00 PM
📍 Chase Village, Trinidad & Tobago
A premium culinary event featuring over 30 gourmet dishes and top-tier drinks.
International Caribbean Events
Fuikdag
📅 Sunday, January 4, 2026
📍 Fuik Bay, Curaçao
A massive floating party where attendees arrive by boat with floaties, drinks, and island vibes.
St. Barths Music Festival
📅 January 9–19, 2026
📍 St. Barths
A multi-day celebration of music and arts featuring performances across the island.
Cayman Cookout
📅 Starting Wednesday, January 14, 2026
📍 The Ritz-Carlton, Grand Cayman
A world-class culinary festival bringing together celebrity chefs, fine dining, and luxury experiences.
Barbados Sailing Week
📅 Starting Thursday, January 15, 2026
📍 Barbados Cruising Club
A major sailing event blending sport, social activities, and island nightlife.
Barbados Flower & Garden Festival
📅 January 16–19, 2026
📍 Speightstown, Barbados
A colorful festival celebrating horticulture, art, and local culture.
Island Exodus
📍 Dominican Republic
A lifestyle and party experience combining music, travel, and beachside energy.
ADN Bachata World Festival
📅 Thursday, January 29, 2026 | 9:00 PM
📍 Puerto Plata, Dominican Republic
A global celebration of bachata music, dance, and Dominican culture.
Flow Fest Punta Cana
📅 Thursday, January 29, 2026 | 8:00 AM
📍 Punta Cana, Dominican Republic
A wellness-meets-music festival featuring fitness, lifestyle, and entertainment.
Ongoing Nature & Cultural Experiences
Live Steel Drums & Street Food Tours – Guided cultural experiences with hotel pickup
Turure Water Steps (Trinidad) – Free natural pools and waterfalls
Main Ridge Forest Reserve Hikes (Tobago) – Explore the oldest protected forest in the Western Hemisphere
Scarlet Ibis Sunset Tours – Boat tours to witness Trinidad’s iconic national bird
January 2026 proves that the Caribbean doesn’t ease into the new year — it bursts into it. With Carnival season ramping up, reggae and dancehall still dominating, and lifestyle festivals spreading across the islands, this is one of the best months to experience Caribbean culture in full motion.
Stay tuned to Caribbean E-Magazine for event recaps, travel guides, and exclusive entertainment coverage all year long.
Which January event are you planning to attend? Share this guide and let us know.