Race Calendar – All Events in Date Order

Race Calendar – All Events in Date Order

Jan
29
Thu
2026
Caribbean Multihull Challenge
Jan 29 – Feb 1 all-day
Feb
13
Fri
2026
Jolly Harbour Valentine’s Regatta @ Jolly Harbour Yacht Club
Feb 13 – Feb 15 all-day
Mar
5
Thu
2026
St. Maarten Heineken Regatta @ St. Maarten Yacht Club
Mar 5 – Mar 8 all-day
May
12
Tue
2026
WindWard 500 Race Series
May 12 all-day
Nov
20
Fri
2026
Jolly Harbour Yacht Club Annual Regatta
Nov 20 – Nov 22 all-day
Jan
23
Sat
2027
Pineapple Cup Montego Bay Race @ Montego Bay Yacht Club
Jan 23 – Jan 29 all-day
Feb
4
Thu
2027
Caribbean Multihull Challenge
Feb 4 – Feb 7 all-day
Feb
12
Fri
2027
Jolly Harbour Valentine’s Regatta @ Jolly Harbour Yacht Club
Feb 12 – Feb 14 all-day
Mar
4
Thu
2027
St. Maarten Heineken Regatta @ St. Maarten Yacht Club
Mar 4 – Mar 7 all-day
May
11
Tue
2027
WindWard 500 Race Series
May 11 all-day
Nov
19
Fri
2027
Jolly Harbour Yacht Club Annual Regatta
Nov 19 – Nov 21 all-day
Feb
3
Thu
2028
Caribbean Multihull Challenge
Feb 3 – Feb 6 all-day
Feb
11
Fri
2028
Jolly Harbour Valentine’s Regatta @ Jolly Harbour Yacht Club
Feb 11 – Feb 13 all-day
Mar
2
Thu
2028
St. Maarten Heineken Regatta @ St. Maarten Yacht Club
Mar 2 – Mar 5 all-day
Nov
17
Fri
2028
Jolly Harbour Yacht Club Annual Regatta
Nov 17 – Nov 19 all-day

© Caribbean Sailing Association 2018