| Jun 5-7, 26 | US Sailing Instructor Course | Training | Meeting | (BWYC) | [evtlnk] |
| Jun 6-7, 26 | Candler Regatta ★ | Regatta | One Design | (StABYC) | [evtlnk][track] |
| Jun 6-7, 26 | NOYC High School Regatta | Regatta | Youth | (NOYC) | |
| Jun 6, 26 | Fleur de Lis | Regatta | Handicap,Offshore | (NOYC/LPWSA) | [evtlnk] |
| Jun 6-7, 26 | Navy Cup | Regatta | Handicap,Offshore,One Design | (NYC) | |
| Jun 6, 26 | Children's Hospital Charity | Regatta | Handicap,Offshore | (FYC) | |
| Jun 13, 26 | Great Circle Race | Regatta | Handicap,Offshore | (MYC) | [evtlnk] |
| Jun 13-14, 26 | BWYC SSF 1 | Regatta | Handicap,One Design | (BWYC) | [nor] |
| Jun 13, 26 | Race to the Coast/Sawgrass #1 | Regatta | Handicap,Offshore | (GYC/SYC) | [evtlnk][track] |
| Jun 13-14, 26 | Billy Bowlegs Regatta | Regatta | Handicap,Offshore | (FWYC) | |
| Jun 15-19, 26 | Hobie 14 Nationals | Regatta | Multihull,RegionalDistrictNationalWorld | (FWYC) | |
| Jun 19-21, 26 Father's Day | GYA Offshore Challenge Cup | Regatta | Handicap,Offshore | (GYC) | [reg][evtlnk] |
| Jun 19-21, 26 Father's Day | Round the Island | Regatta | Multihull | (FWYC) | |
| Jun 26-28, 26 | Gulfport to Pensacola | Regatta | Handicap,Offshore | (SYC) | [evtlnk] |
| Jun 27-28, 26 | USODA Horizon Clinic | Seminar | One Design,Youth | (FYC) | [evtlnk] |
| Jul 11-12, 26 | Meigs Regatta ★ | Regatta | One Design | (FWYC) | [evtlnk][track] |
| Jul 11, 26 | Bastille Day Regatta | Regatta | Handicap,Offshore | (NOYC) | |
| Jul 11-12, 26 | Horn Island Hop | Regatta | Multihull | (OSYC) | [evtlnk] |
| Jul 18-19, 26 | Summer Regatta ★ | Regatta | One Design | (MYC) | |
| Jul 25-26, 26 | Junior Lipton Regatta ★ | Regatta | One Design | (FYC) | [evtlnk] |
| Aug 1-2, 26 | Weatherly Regatta ★ | Regatta | Handicap,One Design | (GYC) | |
| Aug 8-9, 26 | Knost Championship ★ | Regatta | One Design,Women | (PCYC) | |
| Aug 15-16, 26 | Birthday Regatta | Regatta | Handicap,Offshore,One Design | (PCYC) | |
| Aug 22-23, 26 | Galloway GYA Sunfish/Laser Championship | Regatta | One Design,Youth | (GYC) | |
| Aug 22, 26 | Pam Sintes | Regatta | Handicap | (NOYC) | |
| Aug 22-23, 26 | Katrina Memorial | Regatta | Handicap,One Design | (OSYC) | |
| Sep 3-7, 26 Labor Day | Opti Week | Regatta | One Design,Youth | (PYC) | [evtlnk] |
| Sep 5-6, 26 Labor Day wknd | Sir Thomas J. Lipton Interclub Challenge ★ | Regatta | Meeting,One Design | (BWYC) | [reg][evtlnk] |
| Sep 5-6, 26 Labor Day wknd | Labor Day Regatta | Regatta | One Design,Multihull | (GMSC) | |
| Sep 12, 26 | Big Mouth | Regatta | Handicap,Offshore,One Design | (PBYC) | |
| Sep 12-13, 26 | Back to School Regatta/Dinghy Challenge | Regatta | One Design | (PontYC) | |
| Sep 13, 26 | Pink Ribbon Regatta | Regatta | Handicap,Offshore | (NOYC/SYC/LPWSA) | |
| Sep 14-25, 26 | Hobie 16 International Championship | Regatta | Multihull,RegionalDistrictNationalWorld,One D | (OSYC) | |
| Sep 18-19, 26 | Middle Bay Light Regatta | Regatta | Handicap,Offshore | (BucYC) | |
| Sep 18-20, 26 | GYA 420 Championship | Regatta | One Design | ||
| Sep 18-19, 26 | Hobie Wave Grand Prix | Regatta | Multihull,One Design | (GLYC) | |
| Sep 19-20, 26 | Rondinella | Regatta | One Design | (BWYC) | |
| Sep 19-20, 26 | BWCY SSF 2 | Regatta | Handicap,One Design | (BWYC) | [nor] |
| Sep 19, 26 | Great Lake Race | Regatta | Handicap,Offshore | (NOYC/SSYC/CSA) | |
| Sep 19, 26 | Bev Stagg Regatta | Regatta | Handicap | (NYC) | |
| Sep 26-27, 26 | Wadewitz Regatta ★ | Regatta | Handicap,Multihull,One Design,Youth | (FYC) | |
| Sep 26, 26 | Whit Johnson Regatta | Regatta | Handicap | (NYC) | |
| Sep 26, 26 | Round the Cat | Regatta | Handicap,Offshore | (PCYC) | |
| Oct 2-4, 26 | Lost Bay Regatta | Regatta | Handicap,Multihull | (PtYC) | |
| Oct 3, 26 | Rafferty #1 | Regatta | Handicap,Offshore | (PCYC) | |
| Oct 5-10, 26 Columbus wknd | J-22 Worlds | Regatta | RegionalDistrictNationalWorld,One Design | (SYC) | |
| Oct 10, 26 Columbus wknd | Single Handed Round the Lake | Regatta | Handicap,Offshore | (TYC) | |
| Oct 10, 26 Columbus wknd | MYC Charity Regatta | Regatta | Handicap,Offshore | (MYC) | |
| Oct 10-11, 26 Columbus wknd | Fish Class Worlds | Regatta | One Design | (PYC) | |
| Oct 17-18, 26 | Fall Brawl High School Regatta / Great Oaks Qualifier | Regatta | Youth | (FYC) | |
| Oct 17, 26 | Coco Seemann | Regatta | One Design | (SYC) | |
| Oct 17-18, 26 | Shearwater | Regatta | One Design,Multihull | (OSYC) | |
| Oct 17-18, 26 | Hospitality | Regatta | Handicap,One Design,Multihull | (JYC) | |
| Oct 18, 26 | SYC Closing | Regatta | Handicap,Offshore,One Design,Youth | (SYC) | |
| Oct 23-25, 26 | LPRC (NOYC, SYC, TYC, PontYC) | Regatta | Handicap,Offshore | (NOYC/PontYC/SYC/TYC) | |
| Oct 24-25, 26 | WFORC | Regatta | Handicap,Offshore | (PYC) | |
| Oct 24-25, 26 | GYA Melges 15 Championship | Regatta | RegionalDistrictNationalWorld,One Design | (BWYC) | [nor] |
| Oct 24-25, 26 | Hospitality High School Regatta | Regatta | Youth | (JYC) | |
| Oct 24-25, 26 | Monk Smith | Regatta | One Design | (BWYC) | [nor] |
| Oct 31-1, 26 | GYA Fish Class/John G. Curren | Regatta | One Design | (PYC) | |
| Nov 7-8, 26 | NOYC Closing | Regatta | Handicap,Offshore | (NOYC) | |
| Nov 7, 26 | Rafferty #2 | Regatta | Handicap,Offshore | (PCYC) | |
| Nov 7-8, 26 | Guvernator Memorial Regatta | Regatta | Handicap,One Design | (ShYC) | |
| Nov 14, 26 | Knot Round the Rig Race | Regatta | Handicap | (MYC) | |
| Nov 21-22, 26 | Lipton reschedule Date ★ | Regatta | One Design | (BWYC) | |
| Nov 21-22, 26 | Great Oaks Regatta | Regatta | Youth | (SYC) | |
| Nov 26-28, 26 Thanksgiving | USODA Opti Midwinters/GYA Optimist Championship | Regatta | RegionalDistrictNationalWorld | (SYC) |