| 2024 | $151,378.08 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $133,211.10 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $82,685.48 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $67,491.43 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $56,333.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $69,738.56 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $42,760.25 | Wellesley to Bourne (1-Day, Sat) |
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