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Look at it this way. Lots of sailboats get into trouble in that area WITH engines. Combine VERY strong currents with the fact that they do not always flow along the channels and you have a prescription for trouble.
 

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Getting from Great Harbor into Vineyard Sound should be do-able without a motor. It is the passage into Buzzards Bay that is troublesome. In any case it will require good local knowledge and you better have your towing insurance paid up while you are learning the local situation.
 
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