Nantucket is not just for preppies with deep pockets. To enjoy this classic getaway, all you need is a pair of wheels and a sense of adventure.

Buff Strickland The Old North Wharf in Nantucket
| Credit: Buff Strickland

8 A.M.

I wake up to the smell of fresh coffee brewing in the kitchen at the Sherburne Inn (10 Gay St.; 508/228-4425; My room ($105) at the bed-and-breakfast is simple, breezy, and right in the center of town. Though it’s only April (I’ve timed my trip to take advantage of off-peak rates), the late-spring weather is already warm. So I settle into the inn’s porch and enjoy the complimentary spread of walnut breads and French roast.

9 A.M.

Taxis on the island are expensive, but Young’s Bicycle Shop (6 Broad St.; 508/228-1151) will rent you a sporty Trek Hybrid ($30 per day), complete with Nantucket basket. At the store, a friendly local tells me that Great Point beach, near the Wauwinet inn, has miles of secluded shoreline and sweeping views of the Atlantic Ocean. I pocket a free island map at the counter and point my wheels east.

10 A.M.

It’s becoming clear why this beach is so secluded: it’s nine miles from downtown. I make it there, huffing and puffing, and find the dunes blissfully untouched. After dipping my toes in the surf and collecting a few seashells (nature’s freebies), I plunk down in the hull of a beached dory for a quick nap in the sun.

11 A.M.

The $380-a-night rooms at the exclusive, white-fenced Wauwinet (120 Wauwinet Rd.; 800/426-8718) may not be in my budget, but cocktails at the alfresco bar (which welcomes non-guests) are certainly within my reach. I splurge on a mid-morning mimosa ($12) and inhale the salty sea breezes.

12 P.M.

Back in town, I meet my friend Alexandra for brunch at Black-Eyed Susan’s (10 India St.; 508/325-0308), a tiny café known for comfort food with a twist (French toast dipped in Jack Daniel’s and topped with pecans). But it seems that everyone else is meeting a friend here, too: the line stretches for two blocks. ("Come before ten a.m.," the owner says with a shrug.) Instead of waiting, we walk a few blocks to the Even Keel Café (40 Main St.; 508/228-1979), where brunch ($9.50)—rum-battered French toast and a bottomless cup of hazelnut coffee—is just as delicious, and the lines (and prices) more reasonable.

2:30 P.M.

Brunch was a steal—which gives me an excuse to do some shopping. I pop into the Francophile L’lle de France (8 India St.; 508/228-3686), where I eye the steel Cellar Rat candlesticks and a collection of handpainted fleur-de-lis place settings before moving on. At Gypsy (20 Federal St.; 508/228-4404), the Chloé lace blouses and Dsquared2 wool caps are tempting but not within the budget. (A girl can still look, right?) My luck improves at Eye of the Needle (14 Federal St.; 508/228-1923), where I pick up a jeweled Blue Angel T-shirt ($18) marked down from $75.

4:30 P.M.

Sweets are my weakness, so I rationalize a single (okay, double) scoop of butter pecan ice cream ($3) at the nearby Juice Bar (12 Broad St.; 508/228-5799). My cone is so delicious, I begin to wonder if anyone actually orders juice here. I consider a jar of beach plum jam ($5.95), an island favorite, at Nantucket Gourmet (4 India St.; 508/228-4353) but decide to save my money for dinner.

6:30 P.M.

It’s almost sunset, so a 90-minute sail ($35) around the harbor on the 14-seat Endeavor (508/228-5585), which is docked at Straight Wharf, is just the thing. Since it’s BYO for cocktails and food, I decide to cater my own dinner at sea with a split of Korbel champagne ($9.95) from Nantucket Wine & Spirits (31 Sparks Ave.; 508/228-1136) and a lobster roll ($16.75) from the gourmet deli Straight Wharf Fish Store (4 Harbor Square; 508/228-1095).

8 P.M.

Maybe it’s the champagne, or maybe it’s the rocking boat—either way, I’m exhausted when I get back onto dry land. "Meet me for a drink," pleads Alexandra, who is on her way to the Nantucket Lobster Trap (23 Washington St.; 508/228-4200). "I’m buying," she says. Suddenly, I get a second wind, which is fortunate since finding the restaurant takes a little longer than expected. My map is missing (did it go overboard?), so I circle the town, lost.

9 P.M.

Two blocks south of Main Street, I spot the red door of the Nantucket Lobster Trap. Relieved, I step inside to find Alexandra waiting. We order Elbow Benders, the house drink, made with fruit juices, rum, Cherry Heering, and a secret ingredient that gives it a delicious kick. When I add up my tally for the day, I discover that I have enough (well, almost enough) to buy us an order of Nantucket oysters ($14 for six)—served from the raw bar with nothing more than lemon as punctuation. Now I can call it a night.

Total Spent: $253.20

High season runs from June through September. For near-perfect weather and reduced prices, head to the island during the shoulder season in late April, May, or October.


A retro woven-rope bracelet ($4) at the Hub (31 Main St.; 508/325-0200).

Breaking the Budget

Dinner for two ($150) at the Pearl (12 Federal St.; 508/228-9701), chef Seth Raynor’s Asian-influenced seafood hot spot.

Money-Saving Tip

Buy a $1 ticket for the Nantucket Regional Transit Authority (508/228-7025; shuttle bus, which loops the island with convenient drop-off and pickup points (including the beaches). Or spring for the one-day pass ($7).

Drop by the Wauwinet for a meal (dinner for two $170), and catch the free sunset cruise back to town aboard the hotel’s Wauwinet Lady.

Nantucket Lobster Trap

The heart of New England cuisine is seafood, and this restaurant keeps the lobsters alive in their multiple hundred-gallon tanks until they’re ordered. Open for dinner only, the locally owned Nantucket Lobster Trap has both interior and exterior bars, a large dining room and a patio--which is often overflowing with diners during the warmer months. Starters include steamed mussels or calamari, and the menu is naturally lobster-centric: A whole lobster can be prepared boiled or baked and stuffed. Pasta and meat dishes are also available, such as beef tenderloin or chicken breast crusted with potato chips.

Nantucket Gourmet

“Cook with passion” is the motto of Jonathan Stone, who runs this downtown cooking shop with his wife Patty. From pots and pans to food-related gifts and specialty foods, the "Gourmet" has everything aspiring Nantucket chefs and gourmands need to equip their kitchens. Local specialty items available include the Unicorn Magnum pepper gun and a range of jams and jellies from the area, such as tart cranberry marmalade and rose hip jelly. Take-out sandwiches, salads, and paninis are also available, as well as a “soup of the day” like beef barley and Hungarian mushroom.

Juice Bar


A fashion boutique fit for the streets of Los Angeles or New York City, Gypsy was founded by stylist Paola Gonfrade in 2003 to offer shoppers more than the usual pink and green Nantucket fashion. Housed in a 19th-century townhome, this store offers Gonfrade's signature interior design influenced by the nearby shore, with blues and silvers dominating the color palette. Gypse sells a mix of trendy clothing and accessories, and designers like Givenchy, Lanvin, Helmut Lang, and Casmari fill this shop's more than 2,500 square feet of space.

L'Ile de France

Drop by this downtown Nantucket shop to see why it calls itself “The French General Store.” Since 1996, L'Ile de France has been importing directly from its eponymous country. Shelves are lined with housewares and kitchen goods, such as Christian Pineau wicker baskets and hand-painted lamps from Quimper—as well as Quimper's Cornouaille-patterned table settings. The stock also includes home decorations like a santon (a range of Nativity figurines that are both molded from clay and painted by hand) and personal accessories, including leather shoulder bags by Raphaël Mamet.

Even Keel Café

Black-Eyed Susan's

Young's Bicycle Shop

The best way to beach-hop during the days in on the 26 miles of bike paths that trace Nantucket's shores. Young's Bicycle Shop is the time-honored spot for renting cruisers and Bianchis; it offers discounts if you book online.

Sherburne Inn

This eight-room bed and breakfast’s moniker comes from the town of Nantucket’s original name: “Sherburne” or “Sherborn.” Built in 1835 to house offices for the Atlantic Silk Company, the interior of this three-star location is influenced by Greek Revival, French, and English, like the swooping staircase and pine floors. The historic inn isn’t bogged down in its pas though; it’s centrally cooled and has free Wi-Fi. The individually-named rooms have a comfortable New England vibe, including the Cheery Welcome, which contains a four-poster queen bed, and the second-floor King of the Kill that has a private balcony.

The Pearl

One of three Nantucket restaurants operated by Seth and Angela Raynor, this cool, modern space focuses on coastal fare with an Asian twist. White and blue tones, exposed brick, and aquariums set the tone inside at this downtown location. Helmed by executive chef Seth Raynor and chef de cuisine Liam Mackey, The Pearl utilizes locally-sourced seafoods for dishes influenced by the journeys of the chefs. Start with duck confit bao with cucumber pickles and pears and continue with an entrée like the green Thai coconut curry, prepared with tofu and pineapple.

The Wauwinet