Nantucket Without the Mistakes

Nantucket sits thirty miles out in the Atlantic, a fog-colored town of cobbles and cedar shingles that has been receiving arrivals by water since the whaling money built it, and the distance is both the whole romance and the whole logistics problem. The island is expensive, book-early, and unforgiving of improvisation, and nearly every ruined trip traces back to one of five avoidable mistakes. This piece retires all five and leaves the romance intact.

June and September are the correct months, and September is the secret. The ocean is at its warmest after Labor Day, the light goes long and gold across the moors, and the island exhales, rooms easing back from the August peak, tables opening up, the regulars visibly relaxing into their own town. June answers with roses climbing every trellis in Sconset. July and August deliver the full glittering high season and demand bookings made the previous fall to enjoy it. May and October are the value plays, beautiful and half-closed, for travelers who prefer a sweater to a crowd.

Take the slow boat at least one way. The fast ferry from Hyannis does the crossing in about an hour and the traditional boat in a little over two, and the longer trip is the better hour, cheaper, calmer, and the correct arrival, out on deck with coffee as the mainland drops away and the town finally lifts off the horizon, gray and low and exactly as the whalers left it. Do not bring a car. Vehicle passage books out months ahead and costs accordingly, while the parking lots in Hyannis cost less per day and remove the trip's single largest burden in one decision.

The island runs on bicycles, and pedaling out the paved paths, past the ponds and the moors with the smell of salt and scrub pine coming through, is not transportation but one of the principal pleasures on offer. Rent for the full stay the morning you arrive, reserving ahead in summer, and let the public shuttle and the occasional taxi handle the rest. The one legitimate vehicle errand is a day at the far beaches, for which a single day of four-wheel-drive rental with the beach permit, booked ahead, delivers the empty-sand afternoon at a fraction of a week's expense.

Stay in town, within walking distance of the wharves, and take the smaller room this requires without regret, since the town is the amenity, lamplit cobbles, captains' houses, the fog coming up the streets at dusk, and everything worth doing after dinner happens on foot. The out-of-town inns advertise serenity and deliver dependence on the car you correctly did not bring. Summer rooms want booking by January, rental houses a full year out, which sounds like exaggeration and is simply the standing schedule.

Skip the vehicle ferry, as covered. Skip the gated beach clubs, since the public beaches, Surfside for waves, Steps for calm water and that long view, are the equal of anything with a membership. Skip the whaling museum on a rainy day, when the whole island has the same idea, and go the first sunny morning instead, when you will have the sperm whale skeleton and the widows' walks nearly to yourself in one of the best small museums in the country. Skip day-of dinner plans in July, which do not exist. Book the two or three serious tables before the boat, then eat the rest of the week the way the island actually eats, off the counters and the take-out lobster rolls, outside, near the water.

Book in this order: room, boat, bicycles, dinners. Pack a real sweater in every month, since the island runs ten degrees cooler than the mainland believes and the fog is a resident, not a visitor. Take the earlier boat home when the connection matters. And on the last evening, walk out Straight Wharf at dusk, when the harbor takes the light and the masts go black against it. The island has been rewarding the people who planned since the whaling days. By then you will be one of them, which is the entire point of this page.