Nantucket, MA

An izakaya-style downtown room of loud, shareable Asian-leaning small plates: crab fried rice, oyster tacos, and a Peking duck that regulars build their order around. It is widely considered the hardest reservation on the island and worth the effort.

A Venetian small-plates room from the Ventuno family pouring cicchetti, fresh bread with whipped butter, and the smoked-salmon everything-bagel-spice arancini people come back for. Tighter and more interesting than the island's bigger Italian rooms.

A relaxed downtown patio doing globally inflected American plates like Korean pork barbecue and duck carnitas. It hits the gap between fine dining and a clam shack, which is exactly what most nights call for here.

A French bistro inside a 1780s house with a tree-shaded garden terrace and classics done straight: escargot, bouillabaisse, beef bourguignon. It is the island's long-running grown-up dinner that has not chased trends.

A glassy raw bar and seafood room out on Straight Wharf with the harbor right at the rail, built around oysters, a tower, and a long Saturday-lunch scene. The water table and martini-and-shrimp ritual are the reason to book.

A dim, low-lit downtown bar and small-plates room widely called the best cocktails on the island, with food like fluke crudo and roasted duck that keeps pace. It is the late, adult, drink-led room rather than a family dinner.

A casual second-floor room overlooking Madaket Beach doing California-Mexican fish tacos, lobster quesadillas, and sunset margaritas at the far west end of the island. The view and the margaritas are the whole point.

A small downtown room doing coastal Latin cooking, ceviche, and lobster enchiladas with a serious tequila and mezcal list. It is the island's most interesting non-New-England dinner and stays lively late.

A long-running harbor-side dining room on the wharf known for its summer clambake and a bar-and-grille side that is the easier walk-in. Despite the touristy address it has held its kitchen and remains a locals' special-occasion pick.

A tiny cash-friendly counter-and-table spot on India Street famous for its sourdough French toast and a constantly changing globally-wandering dinner menu. The morning line out the door is an island institution, not hype.

A dark 1840s whaling-bar tavern with a downstairs hearth, curly fries, burgers, and chowder, serving the island since 1972. It is the dependable rainy-day, no-reservation, kids-welcome room every regular has a table at.

An unfussy mid-island spot away from the wharves doing acai bowls, big breakfasts, and a fried chicken sandwich, with a sprawling patio. This is the locals' weekday morning room, not a tourist stop.

A garden sandwich shop on Cliff Road famous for enormous house-baked-bread sandwiches and the Portuguese bread loaf people carry off by the armful. It is the standard beach-picnic supply run on the island.

A small box-lunch and sandwich shop on the green in 'Sconset village, the supply point for the Bluff Walk and a beach day at the east end. Squishy sandwiches on soft bread and a porch in the sun are the whole idea.

A small independent coffee bar near the bus terminal with a courtyard, doing proper espresso, matcha, and breakfast sandwiches away from the cruise-day crush. It is the locals' morning caffeine stop, not a chain.

A decades-old seasonal ice cream window near the Whaling Museum scooping house-made ice cream in fresh-pressed waffle cones, with a line that is part of the experience. The single most reliable dessert on the island.

The island's signature walk: a Nantucket Conservation Foundation property running 780 acres from a barn through open moor and meadow down to Ram Pasture and the south-shore ocean. The full out-and-back is the classic moderate Nantucket hike.

The grassland-and-pond turnaround at the ocean end of the Sanford Farm system, open coastal heath running down to an undeveloped south-shore beach. It is the payoff stretch and can also be reached as its own shorter walk.

A dense, enclosed Conservation Foundation loop through red maple, tupelo, and old cranberry-bog wetland on the island's quiet east side. It is the rare shaded, woodland-feeling walk on a treeless island.

A former golf links on the north shore, now an easy open-grassland walk along the bluff with wide Nantucket Sound views and a path down to the beach. It is the short, gentle, view-first option close to town.

A network of dike paths around working and retired cranberry bogs at Polpis, flat walking through wetland, pond, and bog with strong fall color. Quiet, birdy, and almost never crowded.

The Trustees' wild barrier-beach sand spit curling north toward Great Point, all soft sand, cedar, and salt marsh with no shade and no facilities. The harder, remote walk that ends at the Great Point Light.

A small Conservation Foundation reservation with a short path through oak woods out to a boardwalk over salt marsh on a quiet Polpis harbor cove. It is the easy harbor-and-marsh walk with a payoff view at the end.

A research preserve of rare coastal sandplain heathland out toward Eel Point, with mowed self-guided trails through a globally uncommon habitat. The most ecologically interesting easy walk on the island.

A long, low sand spit at the island's northwest tip backed by tidal flats and rich birding, reached by a flat sandy walk past Tupancy and the heathland. A moderate, exposed walk to a wild calm-water point.

The Nantucket Historical Association's flagship museum in a restored 1847 candle factory, with a sperm whale skeleton, scrimshaw, and a harbor-view rooftop deck. The island's main rainy-day cultural anchor and a real museum, family-friendly.

The science nonprofit honoring island-born astronomer Maria Mitchell, running an aquarium, natural-science museum, two observatories, and her birthplace house. The smaller, hands-on, family-leaning museum counterpart to the Whaling Museum.

A professional theatre company staging plays, new work, and a Shakespeare program in an intimate downtown space. It is the island's serious live-performance option, an evening-and-adult pick.

An outdoor brewery, winery, and distillery on a mid-island farm road with live music daily, food trucks, and picnic tables. It is the island's defining open-air afternoon hangout, an outdoor adult scene.

A dive music bar off the mid-island roads running live bands almost nightly in season, the island's only real late-night room. The classic sweaty, after-everything-else, adults-only night.

An eccentric former livestock barn two artist sisters turned into a theatrical summer home in the 1930s, now a small Historical Association house museum. The island's most unusual indoor visit, a quirky quick stop.

The island's oldest and largest family farm, with a big farm market, a field-side food truck, and pick-your-own and event days through the season. A daytime, family-friendly outdoor experience that doubles as the best produce on the island.

The 1834 library whose columned Great Hall still hosts a free in-season program of author talks, music, and lectures. A low-key indoor evening option in the heart of town that costs nothing.

The short white wooden lighthouse at the harbor mouth that every ferry passes on the way in, on a site lit since 1746. It is the picture people take of their arrival and the spot the island says goodbye from, with a sand beach right at its base.

The red-banded 1850 brick tower on the bluff above 'Sconset, moved 400 feet inland in 2007 to outrun the eroding cliff. It sits in open grassland with one of the widest ocean horizons on the island and almost no crowd.

A restored 1847 spermaceti candle factory holding a 46-foot sperm whale skeleton and the original Sankaty Fresnel lens. The rooftop observation deck gives the best free-with-admission view over the harbor and town rooftops.

The island's 1834 Greek Revival library, rebuilt after the 1846 fire, where Frederick Douglass and Ralph Waldo Emerson once spoke in the second-floor Great Hall. It still runs free talks and a quiet reading garden in the heart of town.

The wide cobblestone Main Street, paved in 1837 with ballast stones and lined by the brick mansions whaling captains built after the 1846 fire. It is the unbroken historic core that makes the whole town a landmark, not a generic shopping street.

A narrow public footpath that threads between rose-covered shingled cottages and the open Atlantic on the bluff edge at Siasconset. It crosses private front lawns by long-standing local custom and ends with ocean on one side and some of the island's prettiest gardens on the other.

A 1746 wooden smock windmill, the oldest still working in the United States, built from shipwreck timber and still grinding cornmeal on windy days. It stands on a rise just above town with views back over the rooftops.

A tiny former fishing and actors' colony at the island's east end, all rose-draped shingled cottages, a hand pump in the square, and a market and casino tennis club. It is the quiet anti-town: a village to wander rather than a list of sights.

An 1846 Greek Revival mansion with full white columns built by a whale-oil merchant, now a furnished historic house museum on upper Main Street. It shows how the richest whaling families actually lived behind the famous facades.

The calm, north-shore harbor beach closest to town, with gentle Sound water, a snack shack, and the long stone jetty you can walk out on. It is the island's everyday family flagship beach rather than the wild surf coast.