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| April / 2021 | ||||
| 13/Apr | - | Melges 24 World Championship (CANCELLED) | Charleston, NC, USA | |
| 16/Apr-18/Apr | - | 2020/2021 Etchells Biscayne Bay Series - Mid-Winter East Regatta | Coconut Grove, FL, USA | |
| 17/Apr-19/Apr | - | 2021 St. Croix Yacht Club 28th International Regatta | Christiansted, St. Croix, U.S.V.I. | |
| 17/Apr-19/Apr | - | 2021 Star 45 Icebreaker Regatta | Marblehead, MA, USA | |
| 22/Apr-01/May | - | LI Regata del Sol al Sol | St. Petersburg, FL, USA | |
| 24/Apr-25/Apr | - | 2021 Messmer Cup Regatta | Naples, FL, USA | |
| 24/Apr-25/Apr | - | 2021 Peters & May Round Antigua Race (CANCELLED) | English Harbour, Antigua, West Indies | |
| 25/Apr-02/May | - | Antigua Sailing Week (CANCELLED) | English Harbour, Antigua, West Indies | |
| 30/Apr-03/May | - | 2021 Helly Hansen NOOD Regatta Annapolis | Annapolis, MD, USA | |
| 30/Apr | - | J 111 North American Championship | Annapolis, MD, USA | |
| 30/Apr | - | Palma Superyacht Show | Palma de Mallorca, Spain | |
| May / 2021 | ||||
| 03/May | - | 52 Super Series | St. Tropez, France | |
| 06/May | - | Palma Vela | Palma de Mallorca, Spain | |
| 08/May-16/May | - | Id Crook Snipe World Master Championship (CANCELLED) | St. Petersburg, FL, USA | |
| 09/May | - | OSTAR/TWOSTAR | Plymouth, United Kingdom | |
| 10/May-17/May | - | 2021 J/70 North American Championship | Annapolis, MD, USA | |
| 11/May | - | Maxi Yacht Capri Trophy | Capri, Italy | |
| 15/May | - | ORC European Championship | Capri, Italy | |
| 15/May | - | Regata dei Tre Golfi | Capri, Italy | |