Nantucket: A Serene Summer Escape with Classic New England Charm
Nantucket is the kind of place where “summer” is used as a verb—without a hint of irony. Located just off the coast of Massachusetts, beyond Cape Cod and even farther out than Martha’s Vineyard, this small island is the epitome of upscale New England charm. With its cobblestone streets, weathered gray shingle cottages draped in vibrant hydrangeas, and boutiques brimming with preppy fashion, antiques, and nautical trinkets, Nantucket feels like a living postcard.
I’m not exactly the preppy type, but I do have a soft spot for East Coast beach towns with great food and shopping. So, this past June, I took a quick 45-minute flight from JFK with my two teenage sons for a weekend of exploration and relaxation. Our home base? The Cottages at Nantucket Boat Basin—a sister property to the iconic White Elephant hotel. Nestled along two wharfs in the town harbor, the 31 white-trimmed cottages are surrounded by cozy bars, restaurants, and charming storefronts.
From the moment we arrived, the laid-back luxury of the Cottages set the tone. As we sipped lemonade at the breezy check-in shack, our bags were whisked away to our cottage, High Tide. Perched on the second floor, it featured a private deck with sweeping views of the harbor and coastline. The salty air, the sound of gulls, and the sight of bobbing boats instantly signaled to my senses that it was time to unwind.
Inside, the cottage was a perfect blend of comfort and coastal style: crisp white paneling, striped rugs, rattan lighting, and a smartly stocked kitchenette. Each of the two bedrooms had a spacious en suite bathroom, and a mural of the harbor in colonial times added a touch of history. My bathroom’s oversized sink and shower were pure indulgence.
What I loved most about staying at the Cottages was the feeling of independence. It felt less like a hotel stay and more like living as a local—albeit a very lucky one with prime waterfront real estate.
Visiting just before peak season meant fewer crowds and a more relaxed pace. The weather alternated between sunny skies and cool, misty rain, which took the pressure off doing “all the things.” After settling in, we walked to Natural Foods, a sandwich shop with a hippie vibe, delicious homemade bread, and picnic tables on a sloping lawn. Later, we browsed bookstores, antique shops, and the stylish Staud boutique. At Murray’s Toggery Shop, I was tempted by every tote and anorak. We capped the day with homemade ice cream from the Juice Bar and a seafood dinner on the newly renovated patio at the White Elephant.
The next morning, I slipped out early for coffee at Handlebar Café, a cozy spot with a screen door that snapped shut behind me and a brick patio out front. Normally, I’d be eager to rally the boys for a full day of activities, but instead, I embraced the luxury of not having a plan. With 35 miles of bike paths and complimentary bikes for guests, we set out on a 13-mile ride to Sankaty Head Lighthouse. The route took us through rolling hills, woods, and wildflower-filled fields—so picturesque, it felt like pedaling through a painting. We stopped for lunch in the storybook village of Siasconset and dipped our toes in the ocean before heading back.
A light afternoon rain gave us the perfect excuse to slow down. We each retreated to our rooms—some of us catching up on homework or job applications—before regrouping for a visit to the Whaling Museum’s gift shop and a bit of ferry-watching as new arrivals rolled their bags toward the waterfront bars. The central location of the Cottages made it easy to go our separate ways and reconnect without effort—an ideal setup when traveling with teens.
On Saturday night, we dined at the Wauwinet, a refined Relais & Châteaux property perched on the island’s northeastern edge. With just 33 rooms, the adults-only hotel exudes old-world elegance. We took in the ocean views, snapped photos in the stately sitting rooms, and enjoyed a seafood feast on the enclosed terrace. Afterward, the hotel’s shuttle dropped us back in town, where we wandered the now-familiar streets, savoring our final night.
The next day brought a delayed flight and a plane full of bachelorette parties in matching Nantucket sweatshirts. But that night, as we strolled back to our peaceful harbor cottage, the island’s magic was still with us—quiet, salty, and timeless.
—Jennifer Tung, Senior Director of Wellness and Features at OprahDaily.com
Source: oprahdaily.com