These adjoining and at places overlapping neighborhoods are some of the city's most appealing.

Their streets have been rediscovered by New Yorkers and visitors alike thanks to great shopping and dining opportunities; an impressive new hotel has been added to the mix this year.
The commercial spaces are often large loftlike expanses with witty designs and graceful columns.

The Flatiron District lies south of 23rd Street to 14th Street, between Broadway and Sixth Avenue, and centers around the historic Flatiron Building on 23rd (so named for its triangular shape) and Park Avenue South, which has become a sophisticated new Restaurant Row.
Below 23rd Street along Sixth Avenue (once known as the Ladies' Mile shopping district), mass-market discounters like Filene's Basement, Bed Bath Beyond, Old Navy, and others have moved in.

Flatiron District

The shopping gets classier on Fifth Avenue, where you'll find a mix of national names (including Emporio Armani, Kenneth Cole, Banana Republic, and trendy Restoration Hardware) and hip boutiques.
Lined with Oriental carpet dealers and high-end fixture stores, Broadway is becoming the city's home-furnishings alley; its crowning jewel is the justifiably famous ABC Carpet Home, with 8 floors of gorgeous textiles, homewares, and gifts on one side of Broadway, and an equally dazzling display of floor coverings on the other.

Union Square is the hub of the entire area; the N, R, 4, 5, 6, and L trains stop here, making it easy to reach from most other city neighborhoods.

Union Square
Long in the shadows of the more bustling (Times and Herald) and high-toned (Washington) city squares, Union Square has experienced a major renaissance in the last decade. Local businesses joined forces with the city to rid the park of drug dealers a few years back, and now it's a delightful place to spend an afternoon.
Union Square is best known as the setting for New York's premier green market every Monday, Wednesday, Friday, and Saturday.
Musical acts often play the large pavilion at the north end of the park, and in-line skaters take over the market space in the after-work hours.
A number of hip restaurants rim the square, as do superstores like Toys 'R' Us, the city's best Barnes Noble superstore, and a Virgin Megastore.

From about 16th to 23rd streets, east from Park Avenue South to about Second Avenue, is the leafy, largely residential district known as Gramercy Park. 

Gramercy Park
The pity of the Gramercy Park district is that so few can enjoy the park: Built by Samuel Ruggles in the 1830s to attract buyers to his property in the area, it is the only private park in the city and is locked to all but those who live on its perimeter (the rule is that your windows have to look over the park for you to have a key).
Located at the southern endpoint of Lexington Avenue (at 21st St.), it is one of the most peaceful spots in the city. If you know someone who has a magic key, go there.
Or better yet, book a room at the Gramercy Park Hotel, whose guests have park privileges.

At the northern edge of the area, fronting the Flatiron Building on 23rd Street and Fifth Avenue, is another of Manhattan's lovely little parks, Madison Square.

Madison Square
Across from its northeastern corner once stood Stanford White's original Madison Square Garden (in whose roof garden White was murdered in 1906 by possibly deranged, but definitely jealous, millionaire Harry K. Thaw).
It's now majestically presided over by the massive New York Life Insurance Building, the masterful New York State Supreme Court, and the Metropolitan Life Insurance Company, whose tower in 1909 was the tallest building in the world at 700 feet.