This island institution in West Tisbury opened in 1858, and is one of those adorable country stores that feels like a movie set but is totally authentic (yes, that’s the town’s post office in front, with rows of gleaming mailboxes). Every conceivable inch of the spacious store is stuffed with items ranging from fishing gear and vintage comics to homemade muffins and penny candy. Stop in for a dose of nostalgia before picking up lunch at 7a Foods next door.

From the same owners as Michael Hayes next door, this children's store sells adorable clothes for kids, useful baby gifts and such brands as Melissa and Doug, Cloud B and Claver Sweater.

Opened by a successful interior designer after years spent working on the island, Bespoke Abode sells chic nautical furnishings perfect for the elegant beach home. This isn’t, however, your typical preppy design store; the owner’s eye for the unusual comes through in her collection of vintage swimsuits reminiscent of Jackie O’s iconic summer style.

By day, Black Sheep is the place to go to prep for an artisanal feast filled with enough charcuterie, pâté and fromage to feed a French village. Once night rolls around, however, Black Sheep transforms into Trio, a tapas-style restaurant serving a limited menu of cheese and charcuterie complimented with wine flights and desserts.

Blackstone’s is the place to pick up a gift that says “Boston.” Best bets: a hard copy of Make Way for Ducklings, the beloved children’s book set in Beacon Hill; a preppy tie from Vineyard Vines; or a sailcloth tote from Sea Bags.

Located in Nantucket Town, Bodega sells modern home furnishings as well as one-of-a-kind vintage finds. All the wares are sophisticated but casual, perfect for seaside homes that celebrate island life.

An island institution for decades, this spacious bookstore has a well-edited selection of current titles. Don’t miss the terrific assortment of books about Vineyard life, which includes topics like beach plums, shipwrecks, beach glass and self-published fiction, essays and poetry by island authors. The shop organizes numerous readings every month; check their website for listings.

This treasure chest of a consignment store is crammed full of so many designer and vintage pieces that you may feel overwhelmed. But persevere because here is where you will find a mint condition Brunello Cucinelli pencil skirt only a couple of seasons old for the amazing price of $44. Or a vintage bold and bright Pucci dress or covetable Derek Lam bag. The store only accepts clothes that are one- or two-years  old with exceptions made for mint vintage pieces, and the prices drop significantly after 30 and 60 days.

Jan Campbell was twenty-three when she founded this store in 1985, driven by a love for making fine chocolates and a commitment to hiring young people with special needs and teaching them new skills. Today the company is thriving, and the small cottage in Chilmark is a terrific place to pick up a sweet reminder of your Vineyard vacation.

The spacious two-level gallery, opened decades ago by Christina R. Cook’s parents, exhibits the works of over fifty artists (including Renoir and Cassatt) working in different mediums, from oil and watercolor to etchings. Upstairs in the back you’ll find a fascinating collection of antique nautical maps and charts, gathered by the Coast and Geodetic Survey; some date from 1844 (collecting these maps was a passion of Cook’s father).

Filled with sumptuous items for the home—and overseen by a staff of interior designers who know their field—Christopher’s may be more fun for people who are redoing their homes on the island, but browsing the chic collection can also lead to whimsical finds that just might fit in your luggage.

It’s hard to miss this spot thanks to its prime Easy Street location and quirky retail concept: wine plus 1960s and ’70s vintage dresses. Everything for sale is artfully combined by shopgirl Beth English.

E.R. Butler carries fine architectural hardware yet is also a jewelry store in disguise. The graceful interior and stunning window displays show custom pieces in early American, Federal and Georgian styles plus jewelry by Maria Beaulieu and Paul DeBlassie. Ted Muehling’s candlesticks and porcelain line are highlights.

Situated next to the Charlotte Inn, the Edgartown Gallery was originally built for renowned Martha’s Vineyard painter Ray Ellis, who is a frequent visitor. His Impressionist works set the tone in the elegant space, which is furnished with antiques and overseen by the charming and helpful assistant director.

A fabulous, corner wine store, Épernay specializes in Burgundy and is owned by an expert sommelier.

Eye of the Needle has a store in Palm Beach, but the candy-hued store also fits right into Nantucket, where it is located next to hot-spot restaurant the Pearl. The color-coordinated racks are packed with frilly, preppy fashions that appeal to young adults as much as sophisticated adults.

This one-stop summer shop boasts an impressive collection of casual and outdoor apparel for men and women. The brand uses high-quality and sustainable fabrics, emphasizing their commitment to environmental protection (swimwear is made from plastic bottles and recycled polyester).

Farmaesthetics holistic beauty products have garnered a cult following for such items as Lavender Mist and Almond Blossom soap. The adorable shop on the northern end of Bellevue Avenue also offers facials.

Felix Doolittle’s stationery is one of the country’s best-kept secrets—sort of. Owner and humble watercolorist extraordinaire Felix Fu is a brilliant illustrator who designed the Boston Red Sox’s 2007 holiday card as well as personal stationery for first lady Barbara Bush and Clint Eastwood and who has appeared on Martha Stewart’s and Oprah Winfrey’s shows. Be aware, however, that the West Newton studio, a short drive from downtown Boston, is open only to customers with an appointment. If you can’t make the trip or aren’t interested in a consultation, log on to his Web site, where you can order standard and customized stationery.

A cheese lover’s paradise. From pungent to subtle, cave aged to young and creamy, the selection of European and domestic cheeses includes sharp Vermont cheddars, smooth Brie de Meaux and everything in between. The store, which has another location, in the South End, also carries charcuterie and wines and offers a small take-out menu that’s perfect for picnics.

Paola Gonfrade’s boasts an assortment of designer wares that is delightfully varied. You’ll find Lanvin, Balenciaga and Celine alongside Thakoon and Isabel Marant. The ambiance can be a bit hushed for an island setting, but the fashion is serious and well-edited.

Despite the name, a family, not the university, runs this well-stocked Harvard Square bookstore. Opened in the 1930s, the shop remains a popular place for academics and book lovers from around the city. It’s an excellent spot in which to pass a couple of hours browsing among its broad selection of new and used volumes

With a sister store in Los Angeles, Holiday brings the best of West Coast hip to New England, and traditional Boston loves it. Shopping at Holiday makes you feel as if you’ve just stepped into your fashion-forward best friend’s closet—and she happens to be Cameron Diaz and has an armoire full of Foley & Corinna, Thread Social and Mint. Like your best friend, owner Jessica Pavlic dishes honest advice on which pieces work for different body types, so you can feel confident you’ll make smart shopping decisions.