Rick, if you get to fajardo, provisioning is excellent. You might try the restaurant La Estación. It was a great place two years ago.
We kept our boat at puerto Del Ray 2012/2013. So we have a little bit of experience. I have gone direct from nanny cay to Culebra in an afternoon. It's an easy trip.
There is Google holding in Ensanada behind pirate island (Cayo pirata)
The anchorages on the south side of vieques can be a bit rolly.
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