Written By: Rebecca Lockhart | Photography By: Rebecca Lockhart

There’s something to be said about September on Nantucket. Cooler nights, smaller crowds, and more seats open at your favorite bars and restaurants. While we like to think of autumn on-island as a well-kept secret, some things are just too good to keep quiet. So before switching out your cover-ups for cashmere, treat yourself to one last wave of relaxation on island time with N Magazine’s list of weekend getaway hot spots.

Nantucket, playfully referred to as a “quaint drinking village with a fishing problem,” has mastered the art of fresh local food and artfully-crafted cocktails, even when it comes to sandwiches. Fresh is our one-stop-shop for sandwiches and spirits, offering everything from a seriously stacked Caprese to cold pack of Crispin ciders conveniently available in store or by delivery.

When the sun goes down, nothing will warm you up from the harbor-side breeze quite like the outdoor fire pits at The Nantucket Hotel or a delicious Crucomber at Cru, awarded Nantucket’s best bar by Boston Magazine. For a tasty trifecta of local food, drink, and music, look no further than Atlas, a sleek social spot featuring music by local artists most weekend nights.

As seasoned experts, we’ve crafted the no-fail recovery recipe for feeling fresh after a night out: a dip in the ocean and breakfast from Island Kitchen. Newly renovated with an extended outdoor patio, bar, and ice cream shop, Island Kitchen has been awarded best breakfast and lunch on island. We agree.

While food and drink is a perfectly acceptable way to schedule a weekend, be sure to make time for a few of our favorite island pastimes. Enjoy a performance by White Heron Theatre or discover the history of the island at the beautifully restored Whaling Museum, complete with a rooftop observation deck that offers the most stunning harbor views in town.

Go Figure teaches high-intensity barre classes for all levels in an open boutique studio for early morning energy before a day in the waves at Surfside Beach, easily accessible from town by the Wave. And if there’s one thing you can’t miss, it’s the gorgeous sunset over the water at Steps Beach, best paired with a bottle of wine and a cozy blanket!

A foggy day on the Grey Lady is not only likely, it’s preferred, as the cobblestone streets are lined with carefully curated boutiques that offer something eclectic for everyone. Shop new designers at The Skinny Dip and new sustainable styles at Faherty, both of which offer casual yet unique pieces with the beach in mind. Tucked between cobblestones and covered by ivy, Milly & Grace is a hidden gem in our little black book of boutiques, with a blend of contemporary and classic styles.

For luxury fashion and jewelry, Shari’s Place and The Vault focus on timeless designs sourced from the world’s finest designers. And whether you’re looking to properly thank your weekend host or bring a piece of the island home, 28 Centre Pointe is the newest go-to for beach-inspired home décor, located right in the heart of town.

Ready to book your weekend? Hy-Line and Tradewind Aviation are waiting for you, and so is the Grey Lady.

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