Introduction

madaket boatshed with pink door
photo by Geoff Rand

I can't think of a harbor in Massachusetts that excites more controversy among cruising sailors. To its proponents, Nantucket's gentle island landscapes, seafaring traditions, cobblestone streets and comfortable sense of wealth make it the Grail of regional cruising. It's the one destination on which to focus your mid-winter cruise planning.

To its detractors Nantucket is an overpriced, over-hyped, overly self-absorbed theme park for the rich. They find the obsessively regulated streetscapes antiseptically precious. With too many dress shops. These sailors won't go there unless blown ashore off-season, and then they'll just complain about how you used to be able to anchor anywhere, buy a decent burger, blah blah blah.

Admittedly, it can sometimes be difficult to separate Nantucket the island from "Nantucket" the brand. And the trend is ineluctably towards the megayachts and "premium properties" of a world class vacation destination. Still, for anyone cruising the New England coast, Nantucket has to be considered a life bird.