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It never fails to amaze. I’m strolling along a pleasant street of small brownstones, I come to the corner, and suddenly, the landscape morphs. I’m a small ant in a canyon of skyscrapers, or else I’m a visitor to India, surrounded by cumin-scented restaurants and men with strong accents beckoning me into their curry joints. New York is a city of multiple personalities and like Sybil, they can shift on a dime, within the space of one block going from elegant to seedy, from industrial to chic, from ethnic to all-American.

It’s this quicksilver quality, this constant metamorphosis, that endows even a simple stroll in New York with real excitement. I urge you to spend at least part of your vacation simply ambling around, window-shopping, eavesdropping on passing conversations and exploring places beyond the heavily touristed areas.

Here’s what you’ll find in the various—and strikingly different—neighborhoods of New York City.

DOWNTOWN

The Financial District

Best for: Museums, historic sites (like the September 11 Memorial and Museum), architecture, and access to Ellis Island, the Statue of Liberty, and the Brooklyn Bridge

What you won’t find: Great dining, much evening entertainment

Parameters of the neighborhood: Everything south of Chambers Street

This is where New York City—then New Amsterdam—was born. The area packs the same historic punch as do colonial sections of Boston and Philadelphia. It was on Wall Street that George Washington took the oath of office as America’s first president. It was here, at Fraunces Tavern, that the Sons of Liberty gathered to plot the overthrow of the British. It was at Castle Clinton and then Ellis Island that millions of immigrants flooded the city in the 19th and 20th centuries to get their first glimpse of a "promised land". The great financial movers and shakers also stalked the area (and continue to do so today), and a visit to these "canyons of greed" at the beginning of the day or at 5pm, when those men and women in suits and trader’s smocks pour onto the streets, is an exciting sight. Recent history has overshadowed other sights and for many visitors this has become simply the place to pay respects at Ground Zero. Other top museums here include The Police Museum and The Museum of Jewish Heritage.

Chinatown (& Little Italy)

Best for: Affordable dining and shopping

What you won’t find: Top museums, streets without gridlock

Parameters of the neighborhood: Chinatown is roughly bordered by Broome Street to the north, Allen Street to the east, Worth to the south, and Lafayette Street to the west.

At points, Chinatown takes on the aspects of Shanghai or Beijing: the dense crowds on the streets, the awnings with Chinese characters, the pinging sound of Chinese conversation everywhere. It’s a fun, truly transporting area to visit and one that’s been voraciously swallowing up other neighborhoods—Little Italy, the Jewish Lower East Side—for the past few decades. In fact, except for two blocks of Mulberry Street (from Canal to Broome), strung with colored lights, Little Italy has ceased to exist and is really only a tourist-trapping shadow of its former self. There are a handful of worthwhile places to shop for Italian food, eat gelato or get Italian coffee, but no noteworthy restaurants and very few real Italian-Americans around anymore. For great, cheap eats (and shopping) stick with Asian restaurants and marts, for the most part.

TriBeCa, Nolita & Soho

Best for: Dining, bars, star-sightings, architecture, shopping

What you won’t find: Cutting-edge galleries (they’re now in Chelsea), museums

Parameters of the neighborhood: Let’s explain the names first. SoHo means “south of Houston Street”. This fashionable neighborhood extends down to Canal Street, between Sixth Avenue to the west and Lafayette Street (one block east of Broadway) to the east. Nolita is the area just north of Little Italy (Mott, Mulberry Street and Elizabeth Street north of Kenmare Street). Bordered by the Hudson River to the west, the area north of Chambers Street, west of Broadway, and south of Canal Street is the Triangle Below Canal Street, or TriBeCa. To get here, take the 1 subway to Chambers Street.

Now that we’ve gotten that out of the way, comes the harder task of figuring out what it is about former factories and tenements that the ultra-rich find so appealing. They certainly wouldn’t have wanted to work or live in this area back then, but these formerly industrial areas have been drawing a lot of boldfaced names lately. And with these arrivistes has come a welcome wagon of hot new restaurants, boutiques, spas, and boites. Which means simply wandering these (often) cobblestoned streets, by the cast-iron buildings (Soho has the most of any area in the world) can be a hoot.

The Lower East Side & East Village

Best for: Dining, bars, dance and music clubs, innovative theaters, local designer-clothing shops

What you won’t find: Museums (with the exception of the very fine Tenement Museum and the Museum of Contemporary Art)

Parameters of the neighborhood: Between Houston and Canal streets east of the Bowery

For millions, these areas were once the portal to America. In fact, the buildings you see on the Lower East Side were built expressly to house the teeming masses of immigrants who flooded into New York between roughly 1840 and 1930. At the turn of the last century, this was the most densely populated area in the world, with a dozen to an apartment and pushcarts jamming the streets. While there are some remnants of that life in the old-world fabric and luggage stores along Orchard Street, these areas are mostly known today for bars, lounges, and music clubs. It’s in these two neighborhoods that you’re most likely to find young designers opening their own tiny stores and protégés of the town’s great chefs trying out their own first restaurants. I may be prejudiced because I live in the East Village, but I find it one of the most vibrant areas of Manhattan, though many blocks have lost their gritty edges thanks to ever-rising real estate prices.

Greenwich Village

Best for: Strolling, dining, historic sites, lovely architecture, specialty food shops, theater, live music clubs, star sightings

What you won’t find: Museums, many hotels

Parameters of the neighborhood: From Broadway west to the Hudson River, bordered by Houston Street to the south and 14th Street to the north

Greenwich Village has always been where the city’s outsiders and oddballs have found a haven. In Dutch Colonial times, it was farmland set outside the walls of the city, and a number of slaves were given conditional freedom in return for providing the burghers with food (and fighting off the Native Americans). At the turn of the 20th century, the area became known as a bohemian enclave, where artists of all sorts (Mark Twain, Edgar Allan Poe, Henry James, Winslow Homer, to name a few) could find cheap lodging and companionship. In the 1950s it was at the center of the Beat movement; in the 1960s and [‘]70s the area around Christopher Street became the center of a burgeoning gay rights movement (in the [‘]80s it was a hotbed of AIDS-related activism).

Today, the high real estate prices have dulled the Village’s edge, and you’re more likely to see moms with strollers than long-haired poets walking these streets. And that mom might be Sarah Jessica Parker or Uma Thurman, two of the many celebs who now call the tree-shaded brownstones of the Village home sweet home. But the charms of the area are still intact, as is the illusion that you’ve entered another city altogether. Very few buildings in the neighborhood reach to 10-stories (most are lower than that) and small shops elbow out chain stores. It’s a wonderful place to simply come and get lost in.

MIDTOWN

Chelsea & the Meatpacking District

Best for: Art galleries, nightlife, shopping, the Highline, gay bars

What you won’t find: Theater, Museums

Parameters of the neighborhood: Roughly the area west of Sixth Avenue from 14th Street to 30th Street

Manhattan’s Chelsea neighborhood is today what Soho was 10 years ago, and what Greenwich Village was 20 years ago. The major galleries have moved here, as has Greenwich Village’s large gay population. This makes for a lively cultural scene with many bars and clubs (dance clubs are in abundance from 22nd and 29th streets between Tenth and Eleventh avenues). The so-called Meatpacking District, named for the slaughterhouses in the area, has also become an extremely popular nightlife destination (as well as a shopping mini-mecca for its handful of super-trendy stores). An off-shoot of Chelsea, it’s NYC’s adult Disneyland, filled with late-night clubs, bars, and restaurants that are unhindered by the city’s zoning laws (as there are no schools or churches in this part of town). A final reason to come here: the Highline Park, a marvel of urban reclamation.

The Flatiron District, Union Square & Gramercy Park

Best for: Dining, historic sites, architecture, Off-Broadway theater

What you won’t find: Museums, nightlife (with a few exceptions)

Parameters of the neighborhood: The Gramercy Park area is from about 16th to 23rd streets, east from Park Avenue South to about Second Avenue; the Flatiron District is south of 23rd Street to 14th Street, between Broadway and Sixth Avenue; Union Square is the hub of the district from 14th Street to 18th Street.

If you look up as you meander through these three bustling, adjoining (and overlapping) areas, you’re likely to see brown street signs proclaiming ladies mile. It was on this stretch, mostly on Broadway and Park Avenue South, that the first wave of department stores transformed the lives of New Yorkers in the 1850s. Instead of hopping from a dry goods shop for fabric to a milliners for hats to a cobbler for shoes, women from all over the city came here to outfit themselves and their homes in stores that, wonder of wonders, had everything they needed under one roof. Notice the large plate-glass windows on many of the facades, another department store innovation. Above, the windows are much smaller and point to a second element of the “Ladies Mile”: brothels. When the stores closed for the day, the establishments upstairs opened. And where there’s prostitution, theater often follows. The area around Union Square was New York’s first show district.

Interestingly, the same area has become another important theater district for New York’s Off-Broadway playhouses in recent years. The dining scene is also hot here.

For the best strolling, head directly for the Gramercy Park area, named for the only privately-owned park in the city (the keys go to those apartment owners whose windows overlook the park). Around the park are a number of beautifully preserved historic homes and clubs, including the wisteria-clad home of former Mayor James Harper (4 Gramercy Park S.), the Players Club (at 16 Gramercy Park S; its members included Edwin Booth and Mark Twain), and the National Arts Club (15 Gramercy Park S., a hangout for Woodrow Wilson and Theodore Dreiser).

Times Square & Midtown West

Best for: Theater and entertainment of all sorts, the Museum of Modern Art, Rockefeller Center, Macy’s

What you won’t find: Serenity

Parameters of the neighborhood: From 34th Street to 59th Street west of Fifth Avenue to the Hudson River

Midtown West, a vast area, encompasses several famous names: Madison Square Garden, the Garment District, Rockefeller Center, the Theater District, and Times Square. It’s the area people think of when they think of New York and the reason why so many visitors say with a smirk “Well, it’s a nice place to visit, but I couldn’t ever live there.” And because they’re basing their judgments on crowded, loud, pushy midtown, they’re absolutely right: It’s unlivable . . . which is why so few New Yorkers actually live in this area. In certain parts of Midtown there’s no residential housing whatsoever, and it’s only the tourists who attempt to get a good night’s sleep in this bustling neighborhood.

Midtown East & Murray Hill

Best for: Great architecture, shopping (and window-shopping), historic sites, the United Nations, the Empire State Building

What you won’t find: Museums, nightlife (again, with some exceptions)

Parameters of the neighborhood: East from Fifth Avenue to Third Avenue, north from 42nd Street to 57th Street

In the 1950s, Madison, Park, and Lexington Avenues started to sprout with skyscrapers and soon were rivaling the Wall Street area for office space. That’s primarily what you’ll find here: people in suits, looming glass towers, and lots of traffic. Among all that are some spectacular architectural sights like Grand Central Station, St. Patrick’s Cathedral, the Chrysler Building and the Seagram’s Building. Go closer to the East River and the area becomes largely residential with little to recommend it to visitors beyond Bloomingdales and the United Nations.

A tremendously popular stretch of Midtown East is Fifth Avenue as it runs from 57th Street down to the Empire State Building at 34th Street. Stroll it for some of the best window-shopping on the planet.

UPTOWN

Upper West Side

Best for: Museums (like the American Museum of Natural History and the New York Historical Society), Central Park, bars, kid-friendly restaurants, classical music and dance at Lincoln Center and elsewhere

What you won’t find: Great shopping (again with some exceptions), edge

Parameters of the neighborhood: Starts at 59th Street and encompasses everything west of Central Park.

In some ways, the Upper West Side has the most suburban vibe of any of Manhattan’s neighborhoods. National chain stores line the major thoroughfares and the sidewalks swarm with strollers. It’s a popular area for families thanks to its proximity to Central Park, the American Museum of Natural History, and the Children’s Museum of Manhattan.

It wasn’t always this way. When I was growing up on the Upper West Side, and even before that, the neighborhood had a reputation for being an intellectual hotbed, a place where highly political New Yorkers planned protests. No more. But it’s still an extremely pleasant place to visit with good, if unoriginal, shopping; a handful of topnotch museums; New York’s famous art hub, Lincoln Center; and, of course, access to the glories of Central Park. And the Time Warner Center gives the neighborhood the dubious distinction of having the priciest food court in the world.

Upper East Side

Best for: Museums, architecture, window-shopping, Central Park

What you won’t find: Fine dining (although I list some exceptions to that), theater, music clubs

Parameters of the neighborhood: Starts at 59th Street and encompasses the area east of Central Park

10021 is the richest zip code in the world, and it belongs to the Upper East Side, in particular the swank swatch of pavement that runs from 61st to 80th streets. Also known as “The Gold Coast” and “Millionaires Mile”, this is the stomping grounds for New York’s high society: the Prada-clad women and old money men who sit on the boards of the neighborhood museums, go to a lot of cocktail parties, and endow scholarships for kicks. Their mansions and marble-face townhouses make for nifty sightseeing for those interested in architecture; and the shops along Madison Avenue offer a peek into the extravagant fashions adopted by the ultra-rich and the top designers who serve them.

Museums also play a key role on the Upper East Side, and there’s a greater concentration of top-flight museums here than anywhere else in the country, with the exception of the Mall in Washington, D.C. You’ll want to spend at least 1 day exploring Museum Mile—the Metropolitan, Guggenheim, The Frick, Cooper-Hewitt, and more are all in the area

Harlem

Best for: Dining, bars, clubs, historic sites.

What you won’t find: Theater, shopping, museums (except for the Studio Museum and the Museo del Barrio)

Parameters of the neighborhood: Harlem proper stretches from river to river, beginning at 125th Street on the West Side, 96th Street on the East Side, and 110th Street north of Central Park. East of Fifth Avenue, Spanish Harlem (El Barrio) runs between East 100th and East 125th streets.

Perhaps the most rapidly transforming neighborhood in the city, Harlem is safer and cleaner than it’s been in decades . . . but may be losing some of its intrinsic character. A largely African-American neighborhood since the 1920s—and home to some of the greatest black writers, politicians, and artists of the 20th century—the neighborhood is now drawing an increasing number of Caucasian residents, lured here by lower real-estate prices and the beauty of a brownstone-lined community. My recommendation: Visit here soon before the authentic soul and Caribbean joints disappear, the gospel churches lose their swing, and the rhythm of the streets changes its beat. There’s much to see, including the Studio Museum, dozens of well-preserved Beaux Arts brownstoners, and hopping clubs.

THE OUTER BOROUGHS

Brooklyn

Best for: Museums, parks, lovely architecture, innovative galleries, dining, great views of Manhattan

What you won’t find: You find pretty much all the same types of attractions in Brooklyn that you will in Manhattan. It deserves a visit!

If Brooklyn had not traded its sovereignty to become a borough of New York City in 1898, it would be the fourth largest city in the United States, just after New York City, Los Angeles, and Chicago. With 2.6 million residents (according to the last census), it certainly is the most populous borough of the city and at 71 square miles, it’s also the largest. Which is all a long way of saying it’s very difficult to pin down the nature of Brooklyn, as it’s just too darn big to be summarized in a nutshell.

The two most affluent neighborhoods are Brooklyn Heights, which is right off the Brooklyn Bridge, boasting spectacular views of Manhattan; and Park Slope, the area surrounding Frederick Law Olmstead’s other great work of landscape architecture (after Central Park), Prospect Park. Both are stellar strolling areas, filled with lovely Beaux Arts brownstone buildings (Brooklyn Heights was the first neighborhood in the city to be landmarked).

The borough’s artists tend to live in Red Hook, Williamsburg (though many are getting priced out here), and a few hold-outs still live in DUMBO (the area “Down Under the Manhattan Bridge Overpass”). You can pop by all for afternoons of gallery hopping. Williamsburg has one of the largest Hasidic Jewish communities in the world. Walk the streets peopled by this sect and you may feel as if you’ve stepped back into an old country Shtetl (an illusion only somewhat ruined by the incongruous but ever-present cellphones).

Eastern Europe also makes an appearance in Brighton Beach, which has the largest ex-pat Russian community in the world. It's not the friendliest area, but fascinating to visit nonetheless, with stores selling endless rows of nesting dolls and Lenin t-shirts, and small-scale nightclubs that out-glitz and out-crass Vegas. Just up the shore from Brighton Beach is famed Coney Island, which is open again, despite the ravages of Hurricane Sandy. It’s still an amusement park, though one with less panache than in its heyday.

Among the touristic highlights of the borough are the view from the Brooklyn Heights promenade; Peter Luger, an iconic steakhouse in Williamsburg; the shows at the Brooklyn Academy of Music; and in Park Slope a constellation of sights including the Brooklyn Museum, the Brooklyn Botanical Gardens, and Prospect Park.

The Bronx

Best for: Baseball, Italian restaurants, zoos, and gardens

What you won’t find: Museums, nightlife, other types of noteworthy food, hotels, theater

I may be condemned for this assessment, but to my mind there are only four reasons a tourist should even think of going to the Bronx: Yankee Stadium, the Bronx Zoo, the New York Botanical Gardens, and the Italian restaurants and stores of Arthur Avenue. If you have no interest in any of these sights or facilities, you can skip this giant borough without too much regret.

Queens

Best for: Museums, ethnic dining, affordable hotels

What you won’t find: Theaters, great shopping, top architecture

Archie Bunker no longer lives in Queens. In fact, the grouchy, bigoted xenophobe at the center of the famed 1970s sitcom All in the Family probably wouldn’t recognize the borough today. In just the past 50 years it’s gone from being a somewhat insulated community of Irish- and Italian-Americans to the most international community in the United States.

It’s this ability by tourists to globe trot in an afternoon that makes Queens appealing, despite the dreary, industrial look of much of it. Whether you’re downing samosas or shopping for saris in very Indian Jackson Heights; breaking plates at a Greek restaurant in Astoria; or buying miracle water and tacos at a Mexican botanica in Corona, there’s much to taste, smell, and experience.

Museums are another big draw, and the borough now tops Brooklyn for its cultural attractions, boasting four great ones: The Museum of the Moving Image, PS 1 Museum of Contemporary Art, Isamu Noguchi Galleries, and the Louis Armstrong House.

Staten Island

Best for: Views of Manhattan from the ferry

What you won’t find: Notable museums, nightlife, hotels, theaters, truly great restaurants, interesting architecture

And I’ll again be blunt: Except for the fun and free ferry ride here, there’s no reason a tourist should visit here. Yes, there are a handful of cultural and historic sites, but none that justify the commute.

--Pauline Frommer

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.