UPPER WEST SIDE
Traditionally viewed as Manhattan's last bastion of respectable, middle-class life, the Upper West Side is characterized by huge apartment buildings filled with married couples, boisterous markets choked with strollers and rollerbladers, and the more establishment collegiate crowd, the ones who still wear their fraternity sweatshirts. There are pockets of poverty here too, that have remained impervious to the gentrification around them. After all, West Side Story was based on the Puerto Rican/Irish conflict that took place here in the area now occupied by Lincoln Center. Today, the Irish are gone, but many streets, seemingly at random, have their Puerto Rican populations intact.
Lincoln Center (Broadway at W. 62nd to 66th St; 212/875-5000) is the cultural institution that anchors this gigantic swath of Manhattan, which stretches from 59th Street at Columbus Circle all the way up to Columbia University, above which it becomes Harlem. Lincoln Center comprises the city's main performing arts companies: The New York City Ballet, The Metropolitan Opera, The New York Opera, The New York Philharmonic, and The New York State Theater; it also showcases the world's top music and dance performers in a variety of recital halls. Broadway streams northbound through the Upper West Side's most interesting sights, smells, and shops.
A must-see is the world-famous Zabar's (Broadway at 80th St; 212/787-2000), a food bazaar that redefines ordered chaos. Everyone shops at Zabar's, from regular butcher counter customer Lauren Bacall to your Aunt Sadie. (Just remember: take a ticket!)
The Upper West Side also has some of the city's most famous apartment buildings, chief among them, the Gothic Dakota (W. 72nd St, at Central Park West), setting for Rosemary's Baby and home of John Lennon and Yoko Ono; it was outside the building in 1980 that John was shot and killed. The Ansonia (W. 73rd St, at Broadway) is a wedding cake of an apartment building, a rococo confection of balustrades, turrets, cornices and cupolas, and former (appropriately enough) home of "Glinda the Good Witch" Billie Burke.
The American Museum of Natural History (77th St, between Columbus Ave. and Central Park West; 212/769-5000) is a world-class anthropological institution. Give yourself several hours to explore the exhibits. And don't miss the AMNH's Rose Center for Earth and Space (Central Park West, at W. 79th St, 212/769-5900) -- the old Hayden Planetarium rebuilt from scratch into a spectacular marvel that joins New York's already crowded list of world-class, must-see attractions.
Gays and lesbians on the Upper West Side, while strong in numbers, are decidedly less hip; you'll see more khaki than leather, more sneakers than boots. Amsterdam and Columbus, which run parallel to Broadway, all have very few gay-identified businesses or restaurants.
UPPER EAST SIDE
Stately, dignified, and Waspy, the Upper East Side has always been Manhattan's most elite neighborhood. It was here that the Vanderbilts, the Astors, the Whitneys and the Hewitts built their mansions and made the area synonymous with wealth. Today, the area, bounded roughly by Fifth Avenue to the west, Lexington Avenue to the east, 60th Street to the south and 96th Street to the north, is still home to many of the world's richest and most powerful. Federal-style, stone apartment buildings and quiet, tree-lined streets predominate around Park Avenue to Fifth, while the more glitzy, skyscraper condos are clustered closer to the river.
Park Avenue is almost entirely residential, and is home to New York's high society ladies-who-lunch; Fifth Avenue is more international, with high-rise apartments towering over the park (Jackie O. lived at 1040 Fifth Avenue); Madison Avenue is designer boutique row and is also home to some important galleries dedicated to American artists; and Lexington is notable for Bloomingdales and Orsay (1057 Lexington Ave; 212/517-6400; $19-39) where the ladies-who-lunch, well, lunch.
Third Avenue to the East River, from the 60s to the 80s, is technically Yorkville, a historically German and Hungarian ghetto, much of which consists of low-rise, tenement-style buildings that have long since been gentrified into the surrounding neighborhood. Elements of this neighborhood's ethnic past still exist though, through the many German and Hungarian bakeries along E. 79th Street and on First and Second Avenues.
The Upper East Side is also home to a handful of the world's greatest museums. Museum Mile, on Fifth Avenue at 84th Street begins with the Metropolitan Museum of Art (1000 Fifth Ave, at 82nd St; 212/535-7710). This museum houses the largest collection of art in the Western hemisphere, and is unequalled in chronological scope and global coverage. A definite don't-miss, though the experience could take two lifetimes.
Central Park (bounded by 59th Street to the south; 110th Street to the north; Fifth Avenue to the east and Central Park West to the west) is uptown's biggest perk, and Manhattan's saving, green grace. It is literally the city's playground, and you'll see a cross-section of humanity here like no other, with everyone doin'; their thing. Forested by indigenous trees and craggy here and there with the black granite from which Manhattan erupted, there are lawns for Frisbee playing or sunning (the Sheep Meadow, at 67th Street, is very gay during the summer), boat ponds for boating or paddlewheeling, blacktops and roads for biking or blading, an outdoor theater for Shakespearean drama (the Delacorte; 425 Lafayette Street; 212/539-8500), and benches for taking it all in (yes, this is the theater where fans lined up for hours for free tickets to see Meryl Streep in The Seagull in summer 2001). Bethesda Fountain (enter at 72nd Street and follow the main road) is one of the city's most picturesque and romantic spots, perched at the edge of the Boat Pond. And yes, the park is a no-go at night, for obvious reasons.