Complete Caribbean Events Calendar for 2025: Festivals and Regattas

1• Barbados Sailing Week:   mid-January (events around Jan 10-22, 2025). A coastal racing series culminating in the Mount Gay Round Barbados Race. Expect daytime coastal racing, social nights, and shore-side parties in Bridgetown and Carlisle Bay. The event is organized by the Barbados Cruising Club; entries include one-design and handicap classes.

• Junkanoo (Bahamas) : New Year parades / Boxing Day / selected weekend parades   Junkanoo runs in pockets across the Bahamas through the winter and summer, with the major parades on New Year’s Day and Boxing Day. Street parades start in the early hours and are percussion-driven pageants with costumed bands.
February – March (Carnival season across many islands)

• Trinidad & Tobago Carnival:   Trinidad’s main Carnival weekend fell on Monday, March 3 and Tuesday, March 4, 2025 (the Monday and Tuesday before Ash Wednesday). The season includes calypso and soca contests, Panorama (steelpan) finals, fetes, and the Parade of Bands in Port-of-Spain. Plan for major road closures and very busy hotels.
 
• Dominica Carnival (Real Mas) :  generally aligns with regional carnival timing (early March). Dominica’s events emphasize traditional masquerade and sunrise road parades.
 
• St. Maarten   Heineken Regatta :  early March (March 6–9, 2025 in 2025). A four-day regatta with competitive racing by international crews, and an active social schedule and island parties that attract both sailors and on-shore visitors.
April - May (sailing and jazz season)
 
• Antigua Sailing Week:   late April into early May (April 26 – May 2, 2025). One of the Caribbean’s premier regattas: long offshore races, coastal courses, and a large international fleet. Social events in St. John’s include prizegivings and daily shore-side gatherings.
 
• BVI Spring Regatta & Sailing Festival:   typically in the spring (in 2025 the main regatta and festival activity took place around late March / early April). Events include the Round Tortola race, island invitational races, and nightly regatta village programming.
 
• Saint Lucia Jazz & Arts Festival:   late April into early May (late April – May 2025, with island-wide programming across Pigeon Island, Rodney Bay and Soufrière). The festival mixes international acts with regional performers and includes smaller venue shows as well as headline concerts.
June
 

• St. Kitts Music Festival:   late June (June 26–28, 2025). Three nights of music spanning soca, reggae, R&B and international headliners at Warner Park in Basseterre. The festival combines large stadium shows with smaller island events.

• Various smaller island festivals: and boat gatherings begin to pick up as the summer season approaches.
July
 
• Reggae Sumfest (Jamaica)   mid-July (July 13–19, 2025). Jamaica’s largest music festival, centered in Montego Bay, combining artist nights, beach parties, and special tribute nights. Expect mainstage nights and daytime fan events.
 
• Local midsummer carnivals and cultural events across islands (smaller parades and concerts).
August
 
• Barbados   Crop Over   the multi: week Crop Over season reaches its finale on Kadooment/Grand Kadooment Day (first Monday of August   August 4, 2025). Crop Over runs as a season of parties, calypso and soca competitions, markets and the big masquerade parade that closes the festival. The National Cultural Foundation oversees the program of events.
 
• Grenada   Spicemas (Spice Mas) :  mid-August (key mas/parade days in August 2025, with J’ouvert and Fancy Mas scheduled mid-August). Spicemas includes competitions, street parades, and island concerts.
 
• Many islands hold secondary carnival or cultural festivals in August, a busy month for masquerade and food events.
September - October
 
• Hurricane season note  these months sometimes host postponed events or scaled-down programming if weather interferes; many organizers schedule contingency plans.
 
• Some  one-off regattas, challenger cups, and late-season sailing rallies occur as trade-wind conditions remain favorable.
November - December
 
• Christmas / New Year music and parades   several islands hold cultural parades and festivals in December (including Junkanoo pop-ups across the Bahamas outside the major Boxing Day/New Year’s parades).
 
• End-of-year sailing rallies and holiday events   many marinas host year-end parties and informal regattas tied to the holiday period.

How to use this calendar (quick planning notes)

1.Always confirm the date with the event organiser before booking flights. Carnival and festival dates are traditionally fixed relative to religious holidays (e.g., Carnival before Ash Wednesday) but specific parade or regatta dates and race days are set by local organisers and occasionally change.

2.Book early for headline events. Top carnivals, Reggae Sumfest and Antigua Sailing Week sell out hotels and charters early. For sailing events, reserve berths and marina space as soon as entries open.

3.Consider travel logistics. Carnival parades often close roads; allow extra time for transfers and check shuttle options. For regattas, double-check marina facilities and sister event schedules (many regatta teams race back-to-back at several islands).

4.Health and safety. Carry proof of vaccination or travel insurance that covers event cancellations. Keep an eye on weather forecasts during the June-November hurricane season, especially for water events.

5.Local customs and ticketing. Many festivals run ticketed headline nights plus free community events. Check local tourism boards and official festival pages for verified ticket outlets to avoid scalpers.

Selected quick reference (major events & 2025 dates)

• Trinidad & Tobago Carnival  March 3-4, 2025.

• St. Maarten Heineken Regatta  March 6-9, 2025.

• BVI Spring Regatta  late March / early April 2025 (main week reported around Mar 31–Apr 6, 2025).

• Antigua Sailing Week  April 26 - May 2, 2025.

• Saint Lucia Jazz & Arts Festival  late April – early May 2025.

• St. Kitts Music Festival  June 26–28, 2025.

• Reggae Sumfest (Jamaica)  July 13–19, 2025.

• Barbados Crop Over (Grand Kadooment)  Grand Kadooment (final parade) on August 4, 2025.

• Grenada Spicemas  main mass days in August 2025.

• Junkanoo (Bahamas)  major parades on Boxing Day and New Year’s Day; additional weekend parades throughout the year. 

The 2025 Caribbean festival and regatta calendar shows how deeply culture and sea life define the islands’ rhythm. Each month offers something distinct   from the sound of steelpan and soca during Carnival season to the sight of sails crowding Antigua’s harbors. These events aren’t just attractions; they represent living traditions that connect communities and visitors through music, competition, and shared celebration.

Travelers planning a Caribbean trip in 2025 can use this calendar to match their interests with the right season   Carnival for energy and color, the sailing circuit for sport and camaraderie, or summer festivals for island music and food. No matter when you visit, the region’s mix of regattas, parades, and music festivals ensures that every month delivers a genuine cultural experience and a reason to return.