As you’d expect, Hilton Head  is a shopper’s delight, with an emphasis on upscale stores and prices to match. Keep in mind that hours may be shortened in the off-season (Nov.–Mar.). Here’s a rundown of the main island shopping areas in the order you’ll encounter them as you enter the island.
Associated with the attached residential community, this shopping area on Broad Creek right off the William Hilton Parkway actually comprises three entities, the larger Mall at Shelter Cove, the smaller Plaza at Shelter Cove, and the dockside Shelter Cove Harbour.
The Mall opens at 10 a.m. Monday–Saturday and noon on Sunday and features the usual national stores you’d expect, but with a few typically Hilton Head upgrades like Off 5th/Saks Fifth Avenue Outlet (843/341-2088) and Williams-Sonoma (843/785-2408).
Other neat stores in the Mall are DeGullah Creations (843/686-5210), specializing in authentic Gullah wares, and Blue Parrot (800/252-6653), with gift lines such as Wee Forest Folk and Swarovski Crystal.
The most interesting store at the Plaza is no doubt the flagship location of Outside Hilton Head (843/686-6996, www.outsidehiltonhead.com , Mon.–Sat. 10 a.m.–5:30 p.m., Sun. 11 a.m.–5:30 p.m.), a complete outdoor outfitter with a thoroughly knowledgeable staff (they have a smaller satellite store in Sea Pines). Whatever outdoor gear you need and whatever tour you want to take, they can most likely hook you up.
Shelter Cove Harbour hosts a few cute shops hewing to its overall nautical/vacation theme, such as the clothing stores Camp Hilton Head (843/842-3666, Mon.–Sat. 10 a.m.–9 p.m., Sun. noon–5 p.m.) and the marine supplier Ship’s Store (843/842-7001, Mon.–Sat. 7:30 a.m.–5 p.m., Sun. 7:30 a.m.–4 p.m.).
This well-shaded shopping center on William Hilton Parkway hosts the Lily Pulitzer signature women’s store S.M. Bradford Co. (843/686-6161, Mon.–Sat. 10 a.m.–6 p.m.) and the aromatic Scents of Hilton Head (843/842-7866, Mon.–Fri. 10 a.m.–6 p.m., Sat. 10 a.m.–5 p.m.).
This is the closest Hilton Head  comes to funkier beach towns like Tybee Island  or Folly Beach , though it’s doesn’t really come that close. You’ll find some delightful and somewhat quirky stores here, many keeping long hours in the summer, like the self-explanatory Coligny Kite & Flag Co. (843/785-5483, Mon.–Sat. 10 a.m.–9 p.m., Sun. 11 a.m.–6 p.m.), the hippie-fashion Loose Lucy’s (843/785-8093, Mon.–Sat. 10 a.m.–6 p.m., Sun. 11 a.m.–5 p.m.), and the Caribbean-flavored Jamaican Me Crazy (843/785-9006, daily 10 a.m.–10 p.m.).
Kids will love both The Shell Shop (843/785-4900, Mon.–Sat. 10 a.m.–9 p.m., Sun. noon–9 p.m.) and Black Stone Minerals (843/785-7090, Mon.–Sat. 10 a.m.–10 p.m., Sun. 11 a.m.–8 p.m.).
The Shoppes at Harbour Town are a collection of 20 mostly boutique stores along Lighthouse Road. Probably the most interesting is Match (843/671-4653, www.matchgoods.com , daily 10 a.m.–9 p.m.), an upscale vintage store that acquires antiques, designer items, and home goods through a corporate partnership for resale, and also boasts its own walk-in humidor.
At Planet Hilton Head (843/363-5177, www.planethiltonhead.com ) you’ll find some cute, eclectic gifts and home goods. Other highlights include the clothier Knickers Men’s Store (843/671-2291, daily 10 a.m.–9 p.m.), and the Top of the Lighthouse Shoppe (843/671-2810, www.harbourtownlighthouse.com , daily 10 a.m.–9 p.m.), where many a climbing tourist has been coaxed to part with some of their disposable income.
On South Sea Pines Drive at the Marina you’ll find several worthwhile shops, including an “outpost” location of the great local outfitter Outside Hilton Head (800/686-6996, www.outsidehiltonhead.com ) as well as a good ship’s store and all-around grocery dealer South Beach General Store (843/671-6784, daily 8 a.m.–10 p.m.).
I like to stop in the Blue Water Bait and Tackle (843/671-3060) and check out the cool nautical stuff. They can also hook you up with a variety of kayak trips and fishing charters.
And of course right on the water there’s the ever-popular Salty Dog Café (843/671-2233, www.saltydog.com , lunch daily 11 a.m.–3 p.m., dinner daily 5–10 p.m.), whose ubiquitous T-shirts seem to adorn every other person on the island.
Don’t scoff. Every thrift store connoisseur knows the best place to shop second-hand is in an affluent area like Hilton Head , where the locals try hard to stay in style and their castoffs are first-class. Key stops here are The Bargain Box (546 William Hilton Pkwy., 843/681-4305, Mon., Wed., and Fri. 1–4 p.m., Sat. 9:15 a.m.–12:15 p.m.) and St. Francis Thrift Store (2 Southwood Dr., 843/689-6563, Wed.–Sat. 10 a.m.–3 p.m.) right off the William Hilton Parkway.