Entrants
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| Yacht Name | Home Port | Captain | Date |
| NEITH (HERRESHOFF - 54') | MYSTIC, CT | BROWN, VAN | 06/21/2021 |
| AGLAIA (BUZZARDS BAY 15 - 25') | MARBLEHEAD, MA | FRIED, RICHARD | 06/20/2021 |
| MISTRAL TRIO (BRISTOL 34 - 34') | NAHANT, MA | MOTLEY, HERB | 06/19/2021 |
| BLACK MAGIC (HINCKLEY 41 - 41') | MARBLEHEAD, MA | WALTON, DAVID | 06/18/2021 |
| TANGO (IOD - 33') | MARBLEHEAD, MA | MORRISON, RACHEL | 05/20/2021 |
| BLACKFISH (SPIRIT OF TRADITION - 49') | NANTUCKET, MASSACHUSETTS | ZARRELLA, RON | 05/18/2021 |
| NOVA (CUSTOM SLOOP - 3911') | GLOUCESTER, GLOUCESTER, MA | HARVEY, JONATHAN | 05/09/2021 |
| YANKEE GIRL (MORRIS 36 JUSTINE - 36') | MARBLEHEAD, MA | VANDER SALM, THOMAS | 04/23/2021 |
| POLLY (CUSTOM - 55 10') | TELLURIDE, NH | GALLANT, PETER | 04/05/2021 |
| VIKING (IOD - 33') | MARBLEHEAD, MA | MANCUSI-UNGARO, GREG | 04/05/2021 |
| GRACE (CONCORDIA - 41') | HINGHAM, MASSACHUSETTS | HERDE, MICHAEL | 04/02/2021 |
| GYPSY (IOD - 33') | SWAMPSCOTT, MA | DITTRICH, TIMMY | 04/02/2021 |
| PLEIONE (8 METRE - 48') | MARBLEHEAD, MASSACHUSETTS | DYSON, BRUCE | 04/02/2021 |
