Complete Caribbean Events Calendar for 2026: Festivals and Regattas

January 2026

Barbados Sailing Week

 • January 15–21, 2026 - One of the first major sailing events of the year, with coastal racing and the Mount Gay Round Barbados Race anchoring the schedule.

Grenada Sailing Week

 • January 25–30, 2026 - A key competitive regatta in Grenada and Carriacou that draws regional and international crews.

January - February 2026

Caribbean Multihull Challenge

 • January 29 – February 1, 2026- Multihull yachts open the Caribbean racing season from Sint Maarten / St. Martin.

February 2026

RORC Caribbean 600

 • February 23–27, 2026 - A premier offshore yacht race starting and finishing in Antigua, looping around 11 Caribbean islands over roughly 600 nautical miles. The 2026 race saw competitive finishes in both monohull and multihull divisions.

Carnival of Punta Cana (Dominican Republic)

 • February 20–21, 2026 - Dominican Republic carnival celebration featuring parades, music and local traditions.

March 2026

St. Maarten Heineken Regatta

 • March 5–8, 2026 - One of the Caribbean’s most established sailing regattas with multiple competitive divisions and shore events.

Superyacht Challenge Antigua

 • March 6–10, 2026 - Invitational superyacht racing in Antigua combining performance racing and social functions.

St. Barth’s Bucket Regatta

 • March 12–15, 2026 - High-profile superyacht regatta in St. Barthélemy attracting large yachts and crew.

BVI Spring Regatta & Sailing Festival

 • March 23–29, 2026 - Full week of races, including classic coastal and offshore competition around the British Virgin Islands. Dates were revised earlier in 2025 to this slot for logistical reasons.

SVG Sailing Week

 • March 29 – April 6, 2026 - Nine days of racing linking St. Vincent, Bequia and Canouan, plus cultural events ashore.

April 2026

St. Thomas International Regatta (STIR)

 • Late March / Early April 2026 - Multi-session racing event in the U.S. Virgin Islands with short course and island races.

Antigua Racing Cup

 • April 9–12, 2026 - A series of high-intensity coastal races just ahead of Antigua Sailing Week.

Antigua Sailing Week

 • April 22–26, 2026 - One of the region’s longest-running regattas combining competitive racing and waterfront activity.

Dominican Republic Carnival (Extended Season)

 • April 6–12, 2026 - Carnival takes place in multiple Dominican cities with parades and celebrations.

May 2026

Saint Lucia Jazz & Arts Festival

 • April 30 – May 10, 2026 - Music festival featuring international and regional artists.

Martinique Yole Festival (tentative)

 • May 12–16, 2026 - Traditional wooden boat race and cultural program in Martinique.

June – August 2026

Vincy Mas Carnival

 • June 26 – July 7, 2026 - Major carnival in St. Vincent & the Grenadines with soca music, street parades and local community events.

Note: Summer is generally quieter for major regattas; local racing and smaller cultural festivals operate on individual islands during this period.

October 2026

Aruba Regatta

 • October 18–20, 2026 (approx) - Sailing competition that also includes small boat classes.

Cannabliss SVG

 • Early October 2026 (dates TBC) - Festival focused on wellness, creativity and community workshops.

Diwali / Festival of Lights

 • October 2026 - Celebrated in Trinidad & Tobago, Guyana and other Caribbean communities; includes fireworks and cultural programs.

Halloween & Costume Celebrations

 • October 31, 2026 - Island-wide themed events.

November 2026

Golden Rock Regatta

 • November 6–10, 2026 (approx) - Regatta around St. Eustatius and nearby islands.

Curaçao Regatta

 • November 2026 (TBD) - Community sailing event with multiple boat classes.

Jazz & Music Festivals

 • November 2026 - Jazz and classical music festivals take place across the Bahamas, Dominican Republic and other islands.

Day of the Dead Observances

 • November 2026 - Cultural ceremonies in select islands.

December 2026

Antigua Charter Yacht Show

 • December 4–9, 2026 (approx) - Professional charter industry showcase.

Nine Mornings (St. Vincent & the Grenadines)

 • December 16–24, 2026 - Dawn-to-morning street music, food and ritual gatherings leading up to Christmas.

Christmas & Boxing Day Festivities

 • December 25–26, 2026 - Regional family and community events with parades and beach gatherings.

New Year’s Eve Celebrations

 • December 31, 2026 - Island-wide concerts, fireworks and countdown events.

Context and Notes for 2026

Regattas:

 The Caribbean sailing calendar starts early each year with offshore and coastal racing from January through April and tapers after autumn events. Confirm race notices and entry requirements with official regatta organisers before planning participation.

Carnivals and Festivals:

Carnival celebrations vary by island - some are tied to pre-Lenten schedules (February–March) while others align with local calendars. Cultural music festivals like Saint Lucia’s Jazz & Arts and community events like Vincy Mas provide experience beyond sailing.

Seasonality:

Major regattas avoid summer months due to hurricane risk and reduced trade winds. Local island festivals and smaller sailing events may fill this period.