Sited a bit further out from its sister island, this historic sea-faring home base has launched countless ships from long ago whalers to current high-tech yachts and sport crafts. Like Martha’s Vineyard, it offers idyllic getaway qualities that are easily accessed from the not-too-distant New England mainland.

Nestled just south of the foot of Cape Cod, this iconic New England island is quite accessible yet totally removed from mainland concerns. Generations of locals and A-listers have mingled and shared its low-key pleasures and maritime vibe.