| Jan 9-10, 26 | GYA Winter Meeting | Meeting | Meeting | (PYC) | [nor] |
| Jan 10-11, 26 | Master Driver Team Race | Regatta | One Design | (StPYC) | [nor][reg] |
| Feb 7-8, 26 | Valentine's Regatta | Regatta | One Design | (StPYC) | [nor] |
| Feb 7-8, 26 | USODA Valantine | Regatta | RegionalDistrictNationalWorld,Youth | (StPYC) | [nor] |
| Feb 13-15, 26 President wknd | Helly Hanson Sailing World Regatta | Regatta | One Design | (StPYC) | [nor][reg] |
| Mar 7, 26 | Pennington Cup | Regatta | Handicap | (StPYC) | [nor][reg] |
| Mar 8, 26 | Northshore Cup High School Regatta | Regatta | Youth | (PontYC) | |
| Mar 14, 26 | Two Against the Lake | Regatta | Handicap | (TYC) | |
| Mar 14-15, 26 | Women’s + One Design Invitational | Regatta | One Design,Women | (PCYC) | |
| Mar 15-18, 26 | Winter Lightning Championship | Regatta | RegionalDistrictNationalWorld | (StPYC) | [reg] |
| Mar 21, 26 | PontYC Opening Regatta | Regatta | Handicap,One Design,Youth | (PontYC) | |
| Mar 21, 26 | Jack Dane Finn Regatta | Regatta | One Design | (PCYC) | |
| Mar 21-22, 26 | Wet and Cool (HS) | Regatta | Youth | (FYC) | |
| Mar 27-29, 26 | RS Aero Midwinters | Regatta | One Design | (FWYC) | |
| Mar 28, 26 | Rafferty #3 | Regatta | Handicap,Offshore | (PCYC) | |
| Mar 28-29, 26 | Dogwood | Regatta | Handicap,Offshore,One Design,Youth | (FYC) | |
| Apr 11-12, 26 | Alfonso Jr. Regatta & Sutter Cup | Regatta | One Design,Youth | (GYC) | |
| Apr 11-12, 26 | USSCA Gulf Coast Sunfish Championship | Regatta | One Design | (GLYC) | |
| Apr 17-19, 26 | Suncoast Raceweek | Regatta | Handicap,Offshore,One Design | (StPYC) | [nor][reg] |
| Apr 17-19, 26 | Wetafest | Regatta | One Design | (FWYC) | |
| Apr 18-19, 26 | GYA Opening Regatta ★ | Regatta | Meeting,One Design | (BWYC) | |
| Apr 18, 26 | Rafferty #4 | Regatta | Handicap,Offshore | (PCYC) | |
| Apr 19-26, 26 | USODA Team Trial | Regatta | RegionalDistrictNationalWorld,One Design,Yout | (FYC) | |
| Apr 30-8, 26 | Regatta del Sol al Sol | Regatta | Offshore | (StPYC) | [nor][reg] |
| May 2-3, 26 | Commodore David Taylor Regatta | Regatta | Handicap,One Design | (PCYC) | |
| May 16-17, 26 | Spring Regatta ★ | Regatta | Handicap,One Design | (BucYC) | |
| May 23-24, 26 Memorial wknd | Sugar Bowl Race of Champions ★ | Regatta | One Design | (SYC) | |
| May 23, 26 Memorial wknd | Short-handed Challenge | Regatta | Handicap | (PCYC) | |
| May 24, 26 Memorial wknd | Race for the Case | Regatta | Handicap,Multihull,Youth | (GYC) | |
| May 30-31, 26 | School's Out Regatta | Regatta | One Design,Youth | (PontYC) | |
| May 30-31, 26 | Women’s Handicap Championship for the Drury-Dragon Trophy | Regatta | Handicap | (PCYC) | |
| Jun 6-7, 26 | Candler Regatta ★ | Regatta | One Design | (StABYC) | |
| Jun 6, 26 | Children's Hospital Charity | Regatta | Handicap,Offshore | (FYC) | |
| Jun 13-14, 26 | Billy Bowlegs Regatta | Regatta | Handicap,Offshore | (FWYC) | |
| Jun 13-14, 26 | Race to the Coast/Sawgrass #1 | Regatta | Handicap,Offshore | (GYC/SYC) | |
| Jun 15-19, 26 | Hobie 14 Nationals | Regatta | Multihull,RegionalDistrictNationalWorld | (FWYC) | |
| Jun 19-21, 26 | Round the Island | Regatta | Multihull | (FWYC) | |
| Jun 19-21, 26 | GYA Offshore Challenge Cup | Regatta | Handicap,Offshore | (GYC) | |
| Jun 26-28, 26 | Gulfport to Pensacola | Regatta | Handicap,Offshore | (SYC) | |
| Jul 11-12, 26 | Meigs Regatta ★ | Regatta | One Design | (FWYC) | |
| Jul 18-19, 26 | Summer Regatta ★ | Regatta | One Design | (MYC) | |
| Jul 25-26, 26 | Junior Lipton Regatta ★ | Regatta | One Design | (FYC) | |
| 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 22-23, 26 | Galloway GYA Sunfish/Laser Championship | Regatta | One Design,Youth | (GYC) | |
| Sep 5-6, 26 Labor Day wknd | Sir Thomas J. Lipton Interlucb Challenge ★ | Regatta | Meeting,One Design | (BWYC) | |
| Sep 12-13, 26 | Back to School Regatta/Dinghy Challenge | Regatta | One Design | (PontYC) | |
| Sep 26-27, 26 | Wadewitz Regatta ★ | Regatta | Handicap,Multihull,One Design,Youth | (FYC) | |
| Sep 26, 26 | Round the Cat | Regatta | Handicap,Offshore | (PCYC) | |
| Oct 3, 26 | Rafferty #1 | Regatta | Handicap,Offshore | (PCYC) | |
| Oct 10, 26 Columbus wknd | Single Handed Round the Lake | Regatta | Handicap,Offshore | (TYC) | |
| Oct 17-18, 26 | GYA Fish Class/John G. Curren | Regatta | One Design | (BucYC) | |
| Oct 17-18, 26 | Fall Brawl High School Regatta / Great Oaks Qualifier | Regatta | Youth | (FYC) | |
| Oct 23-25, 26 | LPRC (NOYC, SYC, TYC, PontYC) | Regatta | Handicap,Offshore | (NOYC/PontYC/SYC/TYC) | |
| Nov 7, 26 | Rafferty #2 | Regatta | Handicap,Offshore | (PCYC) | |
| Nov 21-22, 26 | Lipton reschedule Date ★ | Regatta | One Design | (BWYC) | |