Summer Travel 2008: The Islands, Decoded


To me, the "real" Nantucket isn’t fancy. Look, for example, at the old houses. Most (like my family’s), while neither large nor elaborate, are beautiful, if only in their simplicity. And like all beautiful things built near the Atlantic Ocean, they are also deteriorating pains in the ass. Many are painted the island’s unofficial color, Nantucket Red, which is now associated with wealth and privilege but stems from the salt-and-sea-faded surplus red government paint that was once used to cover pretty much every man-made surface here.

This, in essence, is my Nantucket: a rotting treasure, a melting snowflake, both souped up and falling apart. It is private yachts and public beaches, idle summer sun-worshippers and working winter scallopers. It is the $17 million summer homes and the winter nor’easters that wash them away. Ask anyone who actually lives here (and no, they are not reenactors): The island is both quaint and genuine. This fact hits home sometime around October, when the skies get big and the mercury sinks and this trophy of manicured hedges and gilded vessels reverts to a cold and shuttered speck at sea.

During the warmer months, the real value of Nantucket is access to that water. Unlike privatized Martha’s Vineyard (Stomp them Grapes! Go Whalers!), Nantucket is a 360-degree public beach, where everyone’s fun starts at the shoreline.

Example: fishing. Even if you don’t like to fish, you’ll definitely love pretending to. Pack a Something Natural picnic and a growler from Cisco Brewers and stab a surf-casting pole into Smith’s Point or any of the southern beaches—Cisco, "Fat Ladies," even Surfside—past Bartlett’s Farm. In reality, most island fishing has less to do with fish than with friends. (Although, caveat: When the blues or stripers are running, you cannot help but catch one. I’ve watched a tuxedoed dude pull up surfside in a Jeep, toss a line, and—bam—reel in a thrashing keeper. The whole thing took 15 seconds. Both chef and dinner were gone before I could ask about the tux.)

In the protected harbor you can sail or windsurf or, if you have political aspirations, kiteboard. The island expands exponentially by boat—rent a kayak from Sea Nantucket on the Washington Street Extension and explore the uninhabited sandbar of Coatue. At the farthest reach of the harbor, you’ll find the dock of a rather posh hotel called the Wauwinet. And though hunting the world’s largest martini is not technically a water sport, it’s still worth mentioning, if only as a caution. The harbor is lousy with sandbars and sea monsters, especially when returning from said martini in, say, a borrowed dinghy steered by moonlight.

At sunset, libations at the RopeWalk’s back bar are a good capper to a hard day of boating, as is lining up for a BYOB seat at Black Eyed Susan’s. Flip-flops suit the Jetties’ casual beach fare, but you might fancy a blazer to enjoy Le Languedoc or the restaurants at the Club Car and Straight Wharf. No shirt, no shoes? No problem! You can always get service, not to mention a 3-pound lobster, on the porch of Sayle’s Seafood. Afterward, the Club Car train bar (which you might remember as the happy-hour spot on everyone’s favorite Nantucket-based sitcom, Wings…or not) has apéritifs and a surprisingly tolerable piano sing-along. Prep schoolers looking for love and rum—not in that order—crowd the bars of both Straight Wharf and Cap’n Tobey’s, while the gin ‘n’ cigar contingent heads to 21 Federal or the Boarding House.

But all that super-silly superciliousness is checked at the door of the Chicken Box, where carpenters and bridesmaids and yachtsmen, Palm Beachers and Cape Verdeans, and the old, the
young, and the ageless pack in together to cheer a beery jam band (or the Wailers, or Little Feat). The Chicken Box isn’t much, but everyone eventually ends up there…. And in that spirit, bartender-turned-co-owner John Jordin promises he’ll knock a few bucks off the cover charge for anyone who mentions this tip sheet along with my name. Because on a snobby little island like Nantucket, it’s all about who you know.


Go on to the next page to see our Nantucket Cheat Sheet, and discover the best places to stay, eat, and play…