NYC: Getting Oriented
When most of us say “New York City” we are really thinking of Manhattan, the long, narrow island which is just one of the five city boroughs.
The four “Outer Boroughs” are the Bronx, Brooklyn, Queens, and Staten Island. While the Outer Boroughs have much to offer, so far Lipstick Getaways includes only Manhattan information, as most visitors (including me) spend all of their time exploring Manhattan. (One exception is the highly-recommended Brooklyn Bridge walk, which includes taking the subway to Brooklyn.)
Manhattan Layout
At only 13.5 miles long and 2.25 miles wide, Manhattan is much smaller than you might have imagined. Much of the business, finance, entertainment, culture, shopping, dining, and living happens in vertical space: the tall buildings and skyscrapers that line the streets and avenues. Speaking of streets and avenues …
Streets vs. Avenues 
Most of Manhattan north of 14th Street is laid out in an orderly grid, with “Streets” running east and west, and “Avenues” running north and south. It is surprisingly easy to navigate, even for the new visitor!
The Streets are numbered; as you go north, the numbers go up (59th Street is north of 34th Street, which is north of 14th Street).
The numbered Avenues go up as you go west (Third Ave. is west of First Ave). By the way, Sixth Avenue has officially been renamed “Avenue of the Americas” but everyone still calls it “Sixth Avenue.”
Broadway runs diagonally across the entire island from southeast to northwest.
A practical custom: New Yorkers (and guidebooks) always include cross streets when giving an address or directions. For example, “819 Madison Ave., between 68th and 69th St.” This makes it pretty easy to find your way around. Also, remember to give the cross street directions (not just the numbered address) to your taxi driver.
East vs. West
Fifth Avenue is the dividing line between “East” and “West.”
So an address is on “West 52nd Street,” it will be west of Fifth Avenue; and one on “East 52nd” will be east of Fifth Avenue.
The Upper East Side and Upper West Side are neighborhoods east and west of Central Park, north of 59th Street.
Uptown vs. Downtown
Manhattan is the only place I know of where the meaning of “uptown” and “downtown” is relative. But actually, it makes perfect sense: “uptown” is north of wherever you are, and “downtown” is south of wherever you are! If you are headed east or west, you are going “crosstown.”
South of 14th Street, the layout gets more confusing.
Just take it for granted that you will get lost and turned around in Greenwich Village, Soho, Nolita, the Lower East Side, Little Italy, Tribeca, Chinatown, and the Financial District.
Lower Manhattan was settled prior to the establishment of the 1811 grid system, and the streets twist and meander along old cow paths, footpaths, and the shoreline. The disordered layout resembles a plate of cooked spaghetti! Just do your best, consult your map every block or so, ask directions (most folks are happy to help) and enjoy wandering and exploring these fascinating, historic neighborhoods.
