The 2023 fleet included:
Class-AA (50< rating)
| Name | Rated Length | 2023 Rating Factor |
| Denis Sullivan | 62.50 | 1.250 |
| Pride of Baltimore II | 72.36 | 1.292 |
| Sultana | 31.64 | 0.862 |
| Virginia | 77.23 | 1.251 |
Class-A (40<rating<50)
| Name | Rated Length | 2022 Rating Factor |
| Adventurer | 42.40 | 1.185 |
| Liberte * | 49.11 | 1.011 |
| Light Reign * | 42.46 | 1.313 |
| Tom Bombadil * | 37.05 | 1.185 |
| Woodwind | 47.88 | 1.351 |
Class-B (30<rating<40)
| Name | Rated Length | 2022 Rating Factor |
| Bonny Rover * | 40.72 | 0.809 |
| Libertate | 30.33 | 0.878 |
| North Wind | 37.22 | 0.952 |
| Shanty | 33.01 | 0.811 |
Class-C (rating <30)
| Name | Rated Length | 2022 Rating Factor |
| Celebration | 20.94 | 0.911 |
| Farewell | 25.50 | 0.941 |
| Lion of Baltimore * | 20.00 | n/a |
| Norfolk Rebel | 33.44 | 0.795 |
| Ondine * | 26.71 | 0.817 |
| Quintessence * | 20.01 | 0.862 |
| Sea Hawk | 26.98 | 0.927 |
| Summer Wind * | 27.41 | 0.695 |
| Unforgettable * | 21.01 | 0.725 |
| Windsong | 27.58 | 0.792 |
Class-N (Invitational Class: Non-schooners)
| Name | Rated Length | 2022 Rating Factor |
| Bennu | 35.01 | 0.936 |
| Genevieve * | 19.20 | 0.693 |
| Grace | 20.05 | 0.708 |
| Jolly Dolphin | 31.47 | 0.887 |
| Radian | 28.08 | 0.838 |
| Tipsy | 29.38 | 0.857 |
- * These boats will be racing down the Bay in spirit only