9 a.m. Fuel up, then roam the shops
Start your day early at Born & Bread, a beloved neighborhood bakery in the area of downtown known as Petticoat Row (where, beginning in the mid-19th century, a cluster of women-owned shops transformed Nantucket’s commercial heart). Treat yourself to one of their sourdough breakfast sandwiches, stacked with ingredients like organic, cage-free eggs; Vermont Cheddar cheese; and applewood-smoked bacon (about $10), paired with an espresso beverage. If you’re in the mood for more shopping, hit up a few downtown shops that open early: Bodega for home goods with a beachy vibe — think handmade Toluca ceramic trays, Dash & Albert runner rugs, framed coastal prints and hand-woven baskets, and Blue Beetle for stylish women’s clothing and Nantucket-themed gifts and accessories.
11 a.m. Honor an abolitionist legacy
Kick off your deep dive into history with the Frederick Douglass walking tour, beginning at the Nantucket Atheneum’s Great Hall, where Douglass delivered his only Nantucket address on the evening of Aug. 11, 1841 — an impassioned anti-slavery oration to roughly 1,000 attendees during one of America’s first mixed-race abolitionist conventions. Douglass was invited by local abolitionists, including the banker William C. Coffin, after a brief address in New Bedford, and spent three days on the island as the convention’s featured guest. Next, follow the map down Centre Street to the African Meeting House, one of the nation’s few surviving 19th-century Black meetinghouses. Inside, powerful exhibits trace Nantucket’s free Black community and its abolitionist movement with original pews, archival letters and multimedia panels.
12 p.m. Explore colonial treasures
From the meetinghouse, take a short walk to the Jethro Coffin House, built in 1686 and recognized as Nantucket’s oldest dwelling. Wander through its low-ceilinged parlors and hearth kitchen, where wide-plank floors creak underfoot and period furnishings evoke daily life in the 17th century. Informational displays highlight early agricultural tools, original paint colors and family records that chart Nantucket’s transformation from a settlement to a seafaring powerhouse. Then cross the lawn to Hadwen House, now displaying the collection of the Lightship Basket Museum. Inside, more than 100 meticulously woven baskets span three centuries of craftsmanship. Allow 45 minutes to marvel at these delicate works and learn how each basket tells a story of survival, trade and island ingenuity.
1:30 p.m. Stock up, then hit the beach and brewery
Hop on a rented e-bike from Young’s Bicycle Shop ($100 for 24 hours), then ride inland to Bartlett’s Farm, a seventh-generation family-run farm and market perfect for stocking a picnic lunch. Choose from sandwiches, green salads tossed with locally grown herbs and heirloom tomatoes at their peak. Don’t miss the Bartlett’s chicken salad sandwich (chicken salad, honey mustard, Cheddar and pepperoncini on ciabatta, $12). Then follow the sandy back roads toward Fat Ladies Beach, a local spot with fewer beachgoers than the more popular south-shore spots. The shaded dunes provide the ideal spot to spread out a blanket and savor your picnic. Cool off with a dip, and admire the surfers catching clean, peeling waves. On your ride back, consider a stop at Cisco Brewers, an open-air compound blending brewery, distillery and vineyard that’s become an island favorite. Dock your bike, sample a signature Whale’s Tale Pale Ale ($8) or a frosty frozen sangria ($9), and if you’re peckish, grab a bite from the rotating food trucks (Korean BBQ tacos, lobster rolls, pretzel bites) to the soundtrack of live music.
5 p.m. Take a stroll on a cliff walk
Hop back on your bike for the 15-minute ride to the Sconset Bluff Walk. Park near Front Street and follow a narrow path that’s been open to the public since 1892 — a one-mile stretch of weathered cobblestones and boardwalk along Nantucket’s eastern cliffs, overlooking the Atlantic Ocean. On the land side, manicured cottage gardens overflow with roses and hydrangeas; on the ocean side, windswept grasses frame dramatic views of rolling blue waters. Wear sturdy shoes and bring a light jacket — the bluff can be breezy — and plan about an hour to meander the route at a relaxed pace.
7:30 p.m. Catch sunset, and dine among roses
Begin your evening back in town with a photo opp at Brant Point Lighthouse — one of the most photographed spots on the island. Time your visit about 15 minutes before sunset to capture golden light beaming through the beacon’s windows, with the harbor glittering behind you. Dinner is just a short stroll away at Òran Mór (reservations open 30 days in advance), a romantic, rose-covered former residence turned bistro. On the menu are French-infused New England fare like the foie gras torchon paired with Ritz crackers, cream cheese and hot pepper jelly ($32), and the Long Island duck duo: tender honey-mustard-glazed duck confit paired with braised sauerkraut, tart cranberry mostarda and rich, buttery fondant potatoes ($40).
10:30 p.m. Party like a local
If you’re still up for more, walk a few blocks over to the Gaslight, where around 10:30 p.m. the restaurant transforms into a buzzing live-music space. Expect impromptu jam sessions, a rotating lineup of local singer-songwriters, and a laid-back vibe that feels like a house party everyone’s invited to. If you’re feeling even rowdier, take a five-minute walk over to the Chicken Box. Once a humble fried-chicken restaurant on the outskirts of downtown, “the Box” (as regulars affectionately call it) has morphed into Nantucket’s prime dive bar — complete with sticky floors, neon signs and a raucous dance floor where live bands crank up the volume, cheap drafts flow freely, and locals and off‐islanders cut loose until the early hours.