Soooo many choices up here!
Cuttyhunk Harbor (inside) is a must. Very protected, old fashioned place that should not be missed.Edgartown on the Vineyard is great and our favorite place. Oak Bluffs on the Vineyard is honky tonk, noisy, busy, and powerboater heaven. Vineyard Haven is okay, nice little town with walking distance, big harbor, lots of anchoring, big ferries to Cape Cod every hour.Nantucket is a dream location too! Moorings are $55 per night though, but there is limited anchoring out in back of the mooring field.Hope that helps. Sailing up here is great all summer. Prevailig winds are SW all summer, they begin soft in morning, build all day, often to over 20 knots, then die off at night, and begin again the next day. Not much in the way of things to watch out for. Shallow areas are clearly marked, anchoring is nice soft sand and mud everywhere. If you ever run aground it's almost always sand not rocks!EnjoyBob KnottH380