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I was going to suggest Cape Cod. Late summer/early fall is the best time of the year. Summer crowds (and rental costs) are down by then, too. New England in general (from Newport, RI up to Maine) can be nice that time of year.
If you're thinking Turks and Caicos, I'd recommend the Turks and Caicos Club, but there are plenty of nice places to stay there, too.
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1987 Venetian Blue (looks like grey) 930 Coupe
1990 Black 964 C2 Targa
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