Nantucket Over Everywhere

A formula for no regrets

If put in a position in which I could only take one trip per year, you would have to pry my yearly trip to Nantucket from my sunscreened clutches. The eight days my family of three spends there each summer are, without exception, the highlight of my year. I would not trade them for Paris in the spring, a safari on the Serengeti, or the clear Caribbean waters. Does that make me narrow-minded? Perhaps. But I know Nantucket is my happiest place because, for the first time in years, I traveled by plane sans Ativan.

I read (and enjoyed) Keith McNally’s I Regret Almost Everything on this year’s trip. In reflecting on the importance of grandparents and his regret that his parents did not see his own children enough, he writes, “If only life were a rehearsal for the real thing.” I thought to myself, “I would change nothing.” Of course, it’s easy to feel certain of life choices basking on the shore of quiet New England harbor, sailboats drifting by, unshackled by the stressors of work for the first time in months.

My thirties have brought a quiet confidence: an ease in knowing what matters and what doesn’t. Even when life feels unbalanced, I am better at recognizing what is worth my energy. The same perspective applies to family trips. In this season of life, I have no desire to chase the hottest reservation or curate the perfect itinerary. I won’t remember the $500, three-hour dockside dinner spent coaxing a bored six-year-old and apologizing to a husband who loathes shellfish. But I will remember sitting on a bench at sunset, eating dinner from my lap, in the center of town hushed by the retreat of day-trippers.

It is no secret that my enchantment with Charleston continues to wane. The heat, the greed, and the homogeneity continue to chip away at its charm, but above all else, decency is a seemingly rare commodity. Manners and hospitality, once our proudest export, have been eclipsed by unharnessed self-importance with no room for grace. On the rare occasion I drive to my daughter’s school for carpool, I can sit for five minutes or more, waiting for another parent to extend the small courtesy of letting me merge into the line.

Red tank, sandals, woven purse

On Nantucket, we don’t lock the front door. The car key lives in the ignition. One afternoon, my daughter waded out to a sandbar, and the tide came in faster than expected. Another parent noticed her struggling and swam out to help guide her back. I once found a passport (ours, whoops) perched neatly at the beach access after it had fallen out of my tote. It had been rescued and left there by a stranger, untouched by the steady stream of beachgoers. And the driving! Nantucket drivers are so courteous, they’ll make you question every Yankee stereotype. There are so many wonderful things about Nantucket, and everyone will have a different reason for loving it, but for me it’s the refinement of the island and the tact of its people.

A few years of nearly identical trips has provided enough insight to nail a formula that is equal parts structured and freeform. There’s a sweet spot, and when we find it, the whole trip hums. We always rent a house; it feels paramount to the Nantucket experience. I look for places with charm, not polish: outlets that spark a little when you plug something in and cabinets full of mismatched mugs. A house that makes no sense to most people but feels just right to us. The fringe of town is my ideal spot, where I easily reach 20,000 steps daily walking back and forth. Additionally, being able to wash everything before leaving is such a luxury. I love coming home without the added stress of a pile of laundry.

Now that I’ve made my case for the imperfect rental, here are some of the places and things that make our yearly trip special. The island isn’t packed with restaurants or endless activities, and you can find most of it online anyway. This isn’t a guide, and it’s definitely not a tell-all. It’s the rhythm and little rituals that make our one-week escape work for our family of three.

my sunglasses and shorts