1. West Side Cycle Path: Manhattan is usually the toughest part of any trip to New York. The subway can be intimidating and the taxis unreliable. Hiring a bike is a great alternative, and thanks to the West Side Cycle Path, a dedicated cyclists' road that runs the full length of Manhattan, it's a relatively safe one too. The 10km path stretches from Battery Park at the southern tip of Manhattan, and continues along the Hudson River to The Cloisters medieval art gallery in the most northerly reaches of the city. The route takes in some of the city's most exciting neighbourhoods including Downtown, Greenwich Village, Chelsea, SoHo, Midtown, Hell's Kitchen and Harlem. It also offers different perspectives on staple New York sites such as the Empire State and Chrysler buildings. Hiring bikes is simple: there are several outlets around the Midtown section of the path (eg: River Bikes, Pier 63, W23rd St, 1212 967 5444), within the city (eg: Frank's Bike Shop, 553 Grand St, SoHo, 1212 533 6332) or through better hotels.
2. The Upper West Side: The 60-odd block stretch of genteel apartment houses, museums and cultural centres to the west of Central Park, is just about the city's most elegant neighbourhood. It became the world's mental image of New York when the Seinfeld TV show became a hit. For fans, there's an easy way to get acquainted with the show and the neighbourhood, thanks to Kenny Kramer, the real-life deadbeat upon whom Seinfeld's Cosmo Kramer was based. The stand-up comic runs a morning tour around the Upper West Side, pointing out its most famous features and also places featured prominently in the series. Kramer also gives a stand-up show and a tour of his apartment block where he and the comedy's creator, Larry David, lived opposite each other in Seinfeld-style anarchy. For bookings, visit kramerformayor.com.
3. Dumbo: The current so-chic-it-hurts part of town is the former industrial slum known as Dumbo. Short for Down Under the Manhattan Bridge Overpass, Dumbo is a small triangle of streets lined with converted industrial buildings in Brooklyn, immediately across the East River from Downtown. Beneath the intersection of the on and off ramps of the Brooklyn and Manhattan Bridges is a string of cafes, bars and restaurants that the city's coolest currently call hip. A neighbourhood is usually deemed as such once a few art galleries open up, and Dumbo has at least a dozen of them. Among its converted godowns and factories live a community of artists and performers who also hang out at establishments such as Blu Lounge, Quench and The Radio Hole. For information and events check out dumbodirect.com - and don't forget your black turtleneck sweater. Dumbo can be reached from Manhattan by subway via High Street stations on the A and C trains, or York Street Station on the F train.
4. Katz's Deli: Almost every bar and restaurant that has been around for more than half a century has a legend attached to it, and Katz's Deli is no exception. Located on the Lower East Side, Katz's is an institution for not only its enormous slab-like sandwiches but also the most famous scene in that quintessentially New York movie, When Harry Met Sally. You remember, that scene - when Meg Ryan's character demonstrates to Billy Crystal how easy it is to fake an orgasm. It was filmed at one of Katz's hundreds of tables. Of course Katz's was famous before the movie: it has been serving kosher dinners at the corner of Houston and Ludlow streets since 1888. It became embedded in the national conscience when it launched its wartime ad slogan 'Send a Salami to Your Boy in the Army'. (205 East Houston St, tel: 1212 254 2246.)
5. Rainbow Room: There are countless great angles to view the canyons of the world's greatest city, but the classic one is from the Rainbow Room atop the sumptuous art deco Rockefeller Centre. Perched 65 storeys in the air, this is swish New York living at its most opulent. Think Sinatra, think cocktails shaken and stirred, think tuxedos and you have the Rainbow Room. It's not cheap: a beer will cost at least twice what most street-level bars charge, and its signature Bellini - a cocktail of champagne and peach juice - is the price of three glasses of champagne elsewhere. But the view has to be seen to be believed.
Virtually every famous building can be seen from its room-length windows, including a stunning view of the Empire State Building. Get there at dusk when the sun casts warm rusty hues across the city. Casual visitors be warned, a strict dress code applies. (65/F, 30 Rockefeller Centre, 1212 632 5100.)
6. Brighton Beach: New York is famous for its ethnic neighbourhoods and one of the more interesting is Brighton Beach. Settled by Russian immigrants after the fall of communism prompted a renewed diaspora, this Brooklyn neighbourhood on the New York Bay shore has become even more Slavic. While its many community bars and social clubs are holes in the walls frequented by locals, nightlife bars are another matter and places such as Odessa (1113 Brighton Beach Ave, Brooklyn, 1718 332 3223) are among the hippest. It also has a thriving arts scene, centred on the New York Millennium Theatre (1029 Brighton Beach Ave, Brooklyn, 1718 615 9797). Get to Brighton Beach from Manhattan via the Brighton Beach subway station on the B and Q lines.
7. The Lower East Side: As Manhattan's remaining front line, this last bastion of cheap housing is the final refuge of the struggling artist and home to the trendiest nightspots. It is among the most dynamic neighbourhoods in the five boroughs. Once the destination for newly arrived Eastern European Jews, the Lower East Side was transformed in the 1960s by an influx of Hispanics, which in turn has given way to a flood of Fukienese who have extended Chinatown from its traditional confines around Canal Street. For those in the know, this neighbourhood is where it's at. It is a frenetic throb of clubs, live music venues, bars, cafes and restaurants. Among the favourite haunts of the area's young denizens are the Orchard Bar (200 Orchard St, 1212 673 5350) and the Ludlow Bar (165 Ludlow St, 1212 353 0536). For punk and rock fans there are live venues such as The Mercury Lounge (217 E Houston St, 1212 260 4700), where the Strokes got their big break, and Arlene's Grocery (95 Stanton St, 1212 358 1633), where free bands play every night.
8. The Staten Island ferry: Leaving Manhattan every 10 minutes from a terminal near the Stock Exchange, the ferry is the best deal in town. Departing from its piers next to Battery Park in Manhattan's south, the ferries run a non-stop 30-minute voyage to the city's forgotten borough at the southern opening of New York Bay. Although there's nothing on Staten Island to warrant getting off the ferry, the trip is astonishing, offering close-up views of the Statue of Liberty and Ellis Island as well as downtown Manhattan. On board is a kiosk selling snacks, drinks and beer - something unheard of among Manhattan's public services.
9. PS1 Arts Centre: Manhattan has so many art galleries and museums that to list them all would require an entire page. But what about in impoverished Queens, the once industrial borough of New York? Since the Museum of Modern Art opened a new wing in Long Island City, art lovers have been discovering a plethora of venues to indulge their passions in the once-forgotten suburban sprawl across the East River. Prime among them is the PS1 Arts Centre, also in Long Island City. Formerly a state-run public school - hence the initials - it is home to some of the most daring art in the country. (2225 Jackson Ave, Long Island City, 1718 784 2084; Entry: US$4; Open: Wed-Sun, 12pm-6pm. It can be reached by subway by the E and F trains via 23rd St-Ely Avenue station, the 7-train at 45th Rd-Court House Sq station and the G train at Court Square.)
10. Ground Zero: When two hijacked planes crashed into the World Trade Centre towers on September 11, 2001, downtown Manhattan was turned into a giant cemetery. Much has changed since then; the million-tonne heap of twisted steel and debris has been cleared and much of the affected infrastructure surrounding the 16 blocks of devastation has reopened. The neighbourhood now resembles an orderly construction site. The Ground Zero viewing platform has explanatory boards overlooking the site on Rector Street, and the railings of St Paul's Chapel on Fulton Street have become the unofficial repository for goodwill messages, photos of the missing and tokens of love. Easily seen from the corner of Liberty and Church streets is the now-famous cross of steel girders. The area is accessible from any downtown subway station, including the N, R, A, C, E, 1, 2, 3 and 9.