Summer Weekend on Nantucket

By Yankee Magazine

Mar 12 2019


Sailboats at Brant Point Lighthouse, Nantucket.

Photo Credit : Massachusetts Office of Travel & Tourism
Though its historic downtown homes serve as reminders of the sea captains and merchants who once ruled over this former whaling and trading hub, the island of Nantucket today plays host to vacationers looking for a classic New England summer getaway. A little quieter and less of a celebrity magnet than its neighbor, Martha’s Vineyard, Nantucket offers picturesque cobblestone streets, great walking and biking paths, a surplus of casual and fine dining options, and some of the region’s best inns and hotels. Here are some of our favorite ways to spend a summer weekend on Nantucket. For more, check out episode 7 on season 3 of Weekends with Yankee, in which we learn all about Nantucket’s signature style at Murray’s Toggery Shop.
Summer Weekend on Nantucket | Weekends with Yankee
Sailboats at Brant Point Lighthouse, Nantucket.
Photo Credit : Massachusetts Office of Travel & Tourism

Plan Your Perfect Summer Weekend on Nantucket

5 Essential Things to Do on Nantucket


Nantucket is a place made for bicycles, with routes fanning out from downtown in every direction. Of the 30-odd miles of paved paths here, the longest and most scenic is an 18-mile round-trip on the Polpis Road Path that loops past ’Sconset Beach. Bring your bike on the ferry, or rent from a number of local outfitters.

’Sconset Bluff Walk

Enjoy one-of-a-kind access to stunning ocean views at Nantucket’s easternmost tip via the ’Sconset Bluff Walk, a traditional seaside path that has remained open to the public even as the shoreline has filled in with private homes.

Whaling Museum

Honoring the gritty days when Nantucket whalers roamed the seas, this museum — whose collections include a majestic 46-foot-long sperm whale skeleton — tells of the historical hunt for leviathans and our modern quest to save them.

Madaket Beach

Nantucket sunsets are breathtaking, and no visitor to the island should skip watching the day end at this beach. There’s no land on the western horizon to get in the way of the show — just open water and a view that will make memories to last a lifetime.


Get on the water with a rental from Nantucket Community Sailing — which has dinghies up to 19-foot day sailers — or sit back and relax while someone else takes the wheel: The Friendship sloop Endeavor offers daily cruises and charters, while the tall ship Lynx runs educational outings on select weekdays in July and August.

3 Places to Stay on Nantucket

The Wauwinet

Nestled between two beaches, this Relais & Châteaux resort property features 32 boutique guest rooms and four cottages, plus the three-bedroom shingled Anchorage House. Food plays a starring role here, thanks to the on-site restaurant, Topper’s, which offers AAA Five Diamond–winning cuisine.

21 Broad

Boutique specialist Lark Hotels debuted this chic 27-room outpost in 2014 as its second property in the heart of downtown (the other, 76 Main, is also worth checking out). Among the amenities: spa services, a game table, outdoor courtyard with fire pit, and vitamin C showers.

The Barnacle Inn

Tucked into a garden landscape in the historic district about two blocks from the commercial hubbub, the Barnacle Inn serves up folksy charm (handmade quilts adorn its beds) at rates that cater to frugal-minded travelers.

5 Restaurants to Try on Nantucket

Black-Eyed Susan’s

Bring a friend to breakfast here and order the wonderfully eggy Pennsylvania Dutch–style pancakes with Jarlsberg cheese and real maple syrup, then grab a huevos rancheros “for the table.” The lines run out the door on weekends, so arrive early, or come back later for the terrific dinner service.

Lola Burger

A spinoff of the popular bistro Lola 41, this upscale burger joint with more than 30 craft beers is a deft hand with beef patties but also offers tuna, lamb, and falafel versions. The “adult happy meal” includes a quarter bottle of California brut with your burger and fries.

Something Natural

This sandwich spot and bakery on the edge of town is the perfect place to grab a bite before heading out on an island bike tour. Sandwiches — familiar fare like lobster salad and roast beef — are stacked high and served on homemade bread. Don’t miss the fresh-baked cookies.

Brotherhood of Thieves

Choose from a wide selection of typical American dishes and New England seafood favorites, served in either the cozy basement tavern, the light-filled main dining room, or the delightful beer garden.

The Proprietors

Founded by the former owners of famed Nantucket eatery American Seasons, the Proprietors draws on the island’s history as an international whaling hub as inspiration for global dishes rooted in local ingredients. Among the recent offerings: day boat scallops with brown butter dashi, and buttermilk-brined chicken.

More from Yankee: 10 Reasons Why We Love Nantucket | 63 Reasons to Love Cape Cod