When I think back on the places that have left the deepest imprint on me, there’s always a common thread: they feel suspended in time. Whether it’s the centuries-old walls of Lucca in Italy, the rolling storybook hills of the Cotswolds, the colorful vintage cars in Cuba, or the untouched beauty of Sumba Island in Bali—these places feel as though the modern world has politely stepped aside to let their history remain intact. And then, of course, there’s Nantucket.

Our first visit to this little island off the coast of Massachusetts was last summer, and I knew immediately it wouldn’t be our last. As we left, I turned to Freddie and said without hesitation, “This is it. This is our family’s summer tradition.” I had fallen hard for Nantucket’s charm—the kind that sneaks up on you slowly, then refuses to let go.

What makes Nantucket even more special is its paradox. Typically, the more remote and challenging a destination is, the more preserved it feels. Nantucket defies that rule entirely. Getting there is surprisingly simple—a quick 45-minute hop on Tradewind Air from New York—and yet the island still radiates the sense that time has paused. From the plane, the island’s distinct shape appears like a logo etched into the sea, and as the clouds part, you spot boats scattered across the harbor and, if you’re lucky with the weather, Brant Point Lighthouse standing proudly at the shoreline. You can also reach Nantucket by ferry, but there’s something about that Tradewind flight that makes the arrival unforgettable.

Once there, you’ll quickly learn that the island is wonderfully walkable. No cars or Ubers needed, just comfortable sneakers and a readiness to explore. The cobblestone streets, more than two centuries old, tell stories with each uneven step. The heart of Nantucket is its historic downtown, lined with boutiques, cafés, and antique shops. The shopping scene alone is worth the trip, especially if you adore estate jewelry. I still remember stepping into Nantucket Estate Jewelry and meeting Laura, who curates her collection with exquisite taste. That’s where I found a sapphire tennis bracelet that feels more like a piece of history than an accessory.

For our stay, we checked into Greydon House—a 20-room Greek Revival gem dating back to 1850. Everything about it feels quintessentially Americana, from the clapboard exterior to the cozy, history-soaked interiors. We stayed in Room 15, a corner suite with sunlight pouring in and a view of downtown that felt straight out of a postcard. After peeking into a few other rooms, I’d say Room 15 or the Federal Suite are absolute standouts if you’re considering a stay. Each space carries its own quirks and stories, but those two capture the magic most vividly.

If Nantucket has been on your bucket list, here’s a little insider tip: September is the golden window. Locals say it’s the island at its best—everything is still open, but the summer crowds have dwindled. You get the full Nantucket experience, just with a little more breathing room.

And while you’re there, make sure to get out on the water. Ask the Greydon House concierge to book you a sail with Captain Mat on the Blue Peter, a century-old sailboat that feels like stepping back in time. Pair that with a massage at Lavender Farms afterward, and you’ll understand why people never want to leave this island.

Of course, food is half the adventure here, and Nantucket doesn’t disappoint. A few standouts from our trip:

Dinner

• Bar Yoshi — Snag a table on the wharf and watch the sunset with fresh seafood that redefines the word “romantic.”
• Millie’s — No reservations, but worth the wait, especially for a sunset meal.
• American Seasons — A top-tier wine list, impeccable service, and the kind of dinner you’ll talk about long after.

Lunch

• Sayles Seafood — Tucked away but home to the best lobster roll you’ll find.
• Brotherhood of Thieves — The spicy chicken sandwich is unforgettable.
• Provisions — A sandwich shop right on the wharf, perfect for a casual midday bite.
• Walter’s — A locals’ favorite hole-in-the-wall for sandwiches and lobster rolls.

Breakfast & Coffee

• Born & Bread — Everything here is delicious, but the breakfast sandwich is a must. Their pastries? Dangerous in the best way.
• Lemon Press — For those mornings when you’re craving something light, like an açaí bowl, fresh juice, or a perfectly brewed coffee.

Nantucket isn’t just a getaway; it’s a place that captures you. It’s the clapboard houses with weathered shutters, the way the light dances across the harbor, the laughter echoing down cobblestone streets, and the sense that you’ve stepped into a story you never want to end. For me, it’s more than a destination—it’s a tradition in the making, one I hope to return to every year.

So if you’ve been waiting for a sign to book that trip, here it is. Nantucket is calling, and trust me, you’ll want to answer.