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Do you know which harbor the mooring is in? Getting in and out of your harbor safely may be a bigger issue than Woods Hole itself. Woods Hole is a narrow passage between Buzzards Bay and Vineyard Sound. You could daysail all summer without ever needing to go through it. I wouldn't want to go through it engineless but there is a fleet of Cape Cod Knockabouts in Great Harbor that sail through there regularly. I think an outboard would be a great investment in your summer though. A mooring in the area is a valuable thing.
 
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