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A week on Cutty would be pretty tough physically. Tough fishing is best enjoyed in small bites. Other than fishing there isn't much else to do. I'd think it might get repetitive fishing it 6 or 7 nights in a row.
MV offers the whole package, though figuring out the access issues is difficult to say the least. Most people who live on MV would never consider going off island to fish for bass. You've got every kind of bass water you'd want, estuaries, inlets, pond openings, surf, back bay, rocks, moving water, still water, sight fishing, boat fishing, etc,etc, etc. There is also plenty to do nonfishing if you want. It is probably your best option, though hiring a beach guide would be money well spent.
Don't sell Nantucket short, it has easier access than the Vineyard and more consistent summer flyrod fishing, though it lacks the deepwater rocky stuff the Vineyard can offer (and seals can be an issue).
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