Morning
Once a low-rent district filled with galleries and artist lofts, these days SoHo (an acronym for “South of Houston Street”) is best known as a shopper's paradise. Walking the area's streets is like flipping through a luxe catalog of high-end brands, with outlets for Prada, Saint Laurent, Alexander Wang and others. Department stores like Bloomingdale's SoHo and Opening Ceremony offer a range of designers, while vintage haven The Reformation reworks used apparel into affordable—and stylish—gear.
Restaurants in the area tend to be just as high powered. Tried-and-true, Balthazar offers consistently excellent eats and similarly excellent people-watching, thanks in part to the mirrors hanging over the bar. The Dutch, Mercer Kitchen and Jack's Wife Freda are also popular spots. If you can't wait for lunch, you can always try your luck at Dominique Ansel Bakery, which made the Cronut a household word.
Afternoon
Nearby NoHo (a short version of “North of Houston”), is a sliver of a neighborhood with outsized appeal. The former stomping grounds of artists like Andy Warhol and Jean-Michel Basquiat, and once the location for underground music club CBGB (now a John Varvatos store), NoHo is still an undeniably cultural district. Hear live music at Bowery Electric (in the evening), see theatrical performances at The Public Theater (the same, usually) or view art at neighborhood gallery The Hole. Costume and clothing designer Patricia Field sells glittery apparel from her nearby storefront; Dashwood Books stocks a range of beautiful contemporary art and photography tomes; and the Makerbot Retail Store offers 3-D portrait printing, in case you want to take home a bust of yourself (or have one created as a present).
Adjacent to NoHo, the East Village is the neighborhood that Blondie, the Ramones and the New York Dolls made famous in the late 1970s. Today that history is perhaps best explored by visiting record stores like A1, dive bar Continental and punk-rock clothing boutique Trash and Vaudeville. Gem Spa, a newsstand at the corner of St. Marks Place and Third Avenue, is one of the area's longest-running businesses, having opened in the 1920s, and is commonly credited with inventing the egg cream—a classic NYC specialty involving soda water, milk and vanilla or chocolate syrup. Closer to Union Square, the Strand is another long-running neighborhood institution—a 90-year-old stalwart that proudly touts its “18 miles of books.”
Over by New York University, Washington Square Park (and its arch, modeled after the Arc de Triomphe in Paris) is considered the heart of Greenwich Village. A former bohemian mecca, the area is known for clubs like Café Wha? and The Bitter End, where musicians like Bob Dylan, Jimi Hendrix and Patti Smith first played. Perhaps because of its proximity to NYU, the area teems with inexpensive restaurants; two standbys are Mamoun's Falafel for Middle Eastern favorites and Artichoke Basille's for ultra-thick pizza. But in keeping with the rest of the City, the neighborhood offers high-end fare as well. Mario Batali's Babbo continues to be as popular as ever; Blue Hill is famous for its sustainable, farm-to-table cuisine; and Minetta Tavern offers delicious food (say, the $28 hamburger made from prime dry-aged beef cuts) in a boisterous atmosphere.
Evening
The quaint, tree-lined streets of the West Village make for perfect pre- and postprandial walks. The neighborhood is filled with top-notch restaurants; try the meatball sliders at the Little Owl, the burger at the Spotted Pig or pan-roasted seafood at Pearl Oyster Bar. (Just remember to make reservations first.)
Many other downtown neighborhoods feature culinary delights as well: Little Italy, Chinatown and the Lower East Side among them. All offer a hint, too, of their immigrant heritage—and in the case of the Lower East Side, vibrant nightlife as well. If you've saved room for dessert, visit Ferrara in Little Italy for espresso and pastries, Kung Fu Tea in Chinatown for tasty bubble milk tea or the LES staple Russ & Daughters for raspberry rugelach. The latter is within walking distance of another famous institution, Katz's Delicatessen.