Near the beginning of “Moby-Dick,” Ishmael explains why he decided to set sail from Nantucket: “There was a fine, boisterous something about everything connected with that famous old island.” Today, nearly 160 years after being written, that characterization still rings true. Though its downtown cobblestone streets and windswept fringes are now filled with expensive (some say exorbitant) restaurants and elegant cocktail bars, the island still has a swagger. To see it in full swing, linger over pints at one of the many harborside pubs, especially at sundown when sailors and fishing boats return to port.
1) HISTORIC BEARINGS
Main Street is lined with 19th-century storefronts and buckled brick sidewalks that seem to require deck shoes. To bone up on island history, visit Mitchell’s Book Corner (54 Main Street; 508-228-1080; mitchellsbookcorner.com). The venerable 42-year-old bookstore was renovated last year and now includes a spacious second floor that hosts weekly readings by local authors like Elin Hilderbrand and the National Book Award-winner Nathaniel Philbrick. The beloved Nantucket Room remains, with hundreds of titles about island lore.
2) PREPPY IT UP
You can still find a bona fide pair of Nantucket Reds (those iconic pinkish chinos) at Murray’s Toggery Shop (62 Main Street; 508-228-0437; nantucketreds.com). But a crop of snappy boutiques have also opened this season. Jack Wills (11 South Water Street; 508-332-1601; jackwills.com), the first stateside outpost of the British university outfitter, carries jaunty polos, cable-knit sweaters and canvas totes in signal-flag colors. Also new is Milly & Grace (2 Washington Street; 508-901-5051; millyandgrace.com), which sells bohemian-style Yoana Baraschi caftans and tunics, Minnie Rose cashmeres, and embossed-silver jewelry from Waxing Poetic.
3) FISH OF THE MOMENT
One of this summer’s most talked-about new restaurants is Dune (20 Broad Street; 508-228-5550; dunenantucket.com), where the veteran island chef Michael Getter uses local seafood and produce. The intimate, warmly illuminated space has three dining rooms, as well as a patio, but you’ll need to book ahead. Recent menu standouts included the flaky, pan-roasted halibut fillet ($28) and the minty spring-pea soup with tender baby shrimps ($10). Stop by the petite quartzite bar on your way out for a Hot & Dirty cocktail — Thai chili-infused vodka with a splash of olive juice.
4) BEACH MARTINIS
A young, tanned crowd fills the back room of Galley Beach (54 Jefferson Avenue; 508-228-9641; galleybeach.net). The cherished beachside restaurant has become a late-night gathering spot since its 2008 renovation, serving pomegranate margaritas ($16) and the Seaside martini, made with Hendrick’s gin and cucumber ($15). By midnight the party spills outside, where tiki torches and sofas line the sand.
5) ISLAND MARKET
Started in 2007, the Nantucket Farmers & Artisans Market (Cambridge and North Union Streets; 508-228-3399; sustainablenantucket.org) is the first weekly market to grace the island. Now encompassing two blocks of Cambridge Street and one of Union downtown, it showcases the wares of 65 different island farmers and artisans throughout the season (and hosts workshops to encourage other would-be island growers and craftspeople). Keep an eye out for handmade quilts in beach-umbrella stripes from Spoon Home Textiles, freshly picked blueberries and raspberries from Moors End Farm, and baked rugelach and fruit tarts from SuperNatural. Open Saturday mornings (9 a.m. to 1 p.m.) through Oct. 16.
6) SURF AND SEAL
Some of Nantucket’s wildest and most pristine beaches are on the island’s far west end, where it tapers to the twin forks of Eel Point and Smith’s Point. You’ll need a four-by-four with a beach-driving permit — included with most rentals, or available at the Nantucket Police Station for $150. You’ll also need to reduce your tire pressure to maximize traction and minimize environmental damage. But after bumping along hillocky dune trails, you’ll enter onto wide-open, mostly empty shores. There are no amenities to speak of, so bring all the supplies you’ll need for the day: food, water, sunscreen. Oh, and a camera. You might spot gray seals.
7) BREW WITH A VIEW
An afternoon of salty, sandy fun can leave you pretty thirsty. So it’s convenient that the island’s fabled west-end watering hole has reopened this summer as Millie’s (326 Madaket Road; 508-228-8435; milliesnantucket.com). Unlike its predecessor, the Westender, which closed a few years back, Millie’s takes full advantage of the sunset location. The owners, Bo Blair and David Scribner, have added a new menu and a glassed-in second-floor bar that lets you drink in panoramic vistas along with your Grey Lady or Whale’s Tale Pale Ale, both from the Cisco Brewery a few miles down the road.
8) BAJA STYLE
Corazón del Mar (21 South Water Street; 508-228-0815; corazonnantucket.com), the latest venture from the seasoned island chefs Angela and Seth Raynor, has attracted a slavish following since opening last summer. The cozy, tiny papaya-orange den — the downstairs has 7 tables and 10 bar stools; the upstairs, 9 tables and a tequila bar — turns out south-of-the-border-inspired dishes like sea-scallop ceviche dressed in chili-citrus aji sauce ($17) and soft, Baja-style tacos filled with beer-battered cod, cabbage slaw and spicy aioli ($22). After dinner, take a stroll along Straight Wharf to Nantucket Ice Cream (44 Straight Wharf; 508-332-4949; nantucketicecream.com) for a cone or the house specialty: a sandwich of lemon sugar cookies and blueberry ice cream ($5.50).
9) SEA SAVIORS
More than 700 shipwrecks litter the treacherous shoals and surrounding waters around Nantucket. For a fascinating glimpse into the island’s underwater heritage, head to the Nantucket Shipwreck & Lifesaving Museum (158 Polpis Road; 508-228-1885; nantucketshipwreck.org). Reopened last year after a $3 million expansion, the museum has vintage “surfboats” once used to save wreck survivors, child-friendly exhibits on Coast Guard sea dogs, and — most chillingly — grainy black-and-white 1956 film footage of one of the most infamous wrecks, the Italian ship Andrea Doria, slowly listing into the sea after its collision with a Swedish ocean liner.
10) BEACHSIDE BRUNCH
Old-school islanders tsk-tsked at the news this spring that the celebrity chef Todd English was redoing the menu at the Summer House Restaurant in Siasconset village (17 Ocean Avenue; 508-257-4542; thesummerhouse.com). The restaurant, however, is still the island’s most civilized spot for lunch, especially at its umbrella-shaded Beachside Bistro. Besides, Mr. English only jazzed up the summertime classics, like a crab cake with corn salsa and tarragon aioli ($24), and a warm poached lobster salad with green beans and beurre blanc ($29).
11) NOT QUITE OPEN HOUSE
The Bluff Walk in Siasconset village was once the south shore’s most fiercely guarded secret. But though you’ll probably share the unmarked path with other visitors these days, a stroll here is still breathtaking. Pick up the trail in the village center (take a right and then a quick left at the end of Front Street) and walk along the high, Atlantic-skirting bluffs, past the backyards of some of the island’s stateliest gray-shingled mansions. Erosion has left its mark (the last third of a mile, which used to extend all the way to Sankaty Head lighthouse, is now closed). But just stay on the path, keep your voice down and wear long pants — some residents, whether intentionally or not, let their sections become overgrown.
IF YOU GO
JetBlue is among the airlines that fly nonstop to Nantucket from New York; it has daily flights from Kennedy Airport through mid-September. A recent Web search found fares from $117. The Nantucket Regional Transit Authority (shuttlenantucket.com) runs shuttle buses all over the island, but a rental car with four-wheel drive is recommended.
The Cottages & Lofts at the Boat Basin (24 Old South Wharf; 866-838-9253; thecottagesnantucket.com) has 24 shipshape cottages that are perched along Nantucket Harbor wharves. Rates start at $520.
The Union Street Inn (7 Union Street; 888-517-0707; unioninn.com) has 12 rooms in a 1770 house, along with Frette robes and modern baths. Rooms from $299.
The White Elephant (50 Easton Street; 800-445-6574; whiteelephanthotel.com) is downtown Nantucket’s only true resort property, with a harborside patio, a restaurant, a spa and 64 rooms, suites and cottages; rates from $680.