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Let’s be frank here—Washington’s real strength is its cultural offerings, not its shopping opportunities. True, Georgetown has some good boutiques along Wisconsin Avenue and M Street, but not as many as you might expect, and they tend to be buried among mediocre chains. One thing D.C. does do extremely well, however, is High Prep: between unique shops like Sherman Pickey and Magic Wardrobe and more widespread brands like Fornash Designs, Vineyard Vines and J. McLaughlin, you will be all set for your next weekend on Nantucket or dinner at the Chevy Chase Club.

The best place to start a Georgetown walk is the 1600 block of Wisconsin Avenue (at Reservoir Road), where you’ll find both antiques shops (Marston Luce) and fashion boutiques (Sugar, Urban Chic). Head south (downhill) for seven blocks, then take a right on M Street (skip Georgetown Park, a giant mall with a predictable selection) and swing over to Cady’s Alley for home design. (Cady’s Alley can be a bit tricky to find; take a left on 33rd Street and go south half a block, or enter on M Street, right next to Waterworks.) Some spots to refuel along the way: Pâtisserie Poupon (Wisconsin, near Q St.), Café Bonaparte (Wisconsin and P St.), and Leopold’s (Cady’s Alley).

INDAGARE TIP: To layer your Georgetown experience with more local flavor, start off with a trip to the formal gardens at Dumbarton Oaks (on R Street), then head over to Wisconsin, veering off periodically to explore such quaint side streets as N and 31st (both east of Wisconsin), where you’ll see lovely brick National Historic Landmark town houses shaded by magnolia trees, behind cast iron fences. Or stop by historic house Tudor Place.