Traveller's Guide: Alternative New York tours

From birdlife to biking, tombs to tunnels, sign up for an adventure that gets under the skin of the Big Apple, says Claire Prentice

Hip-hop Tours of The Bronx and Harlem

Hip-hop is to New York what country music is to Nashville. As we walk (accompanied throughout by a hip-hop soundtrack), guide Jerry Dee Lewis, or JDL to use his hip-hop moniker, explains hip-hop's four elements. These consist of DJing, MCing, B-boying (or breakdancing) and graffiti writing. "Hip-hop went global when the Rock Steady Crew from the Bronx appeared in the film Flashdance in the 1980s but what a lot of people don't know is hip-hop has been going on since 1973," says JDL.

Stops include the "Graffiti Hall of Fame", where invited graffiti artists have transformed the playground walls of the Jackie Robinson school. JDL points out Temple No 7, the mosque where Malcolm X preached in the early 50s, as we head for an unprepossessing discount store, Conway, which at one time housed New York's most influential hip-hop club.

"It's a crime that this is what it's become," he says. We finish up at 125th Street – "the heartbeat of Harlem" – home to the Apollo Theatre. "You can hear hip-hop all over the world, but to really understand it you have to come to the Bronx and Harlem to see where it began."

Hip-hop tours (001 212 209 3370; hushhiphoptours.com). Four-hour bus tour, Fri and Sat, 11am, cost $68. Two-hour walking tour, Tues to Thurs, 12noon, cost $28.

Green-Wood Cemetery

The 474-acre Green-Wood Cemetery in Brooklyn is New York's great Victorian "City of the Dead". "More than 600,000 people are buried here, so if you've come hoping to find your Uncle Bob you'll probably be disappointed," says guide Mariel Isaacson. Landscaped cemeteries on the outskirts of the city were a new concept in the 1830s and the public was initially slow to warm to the idea of a burial place accessible only by ferry, from Manhattan. But after the Depression eased, people began buying plots.

The list of those buried here includes the rich and famous, from Leonard Bernstein and the Tiffany jewellery family to John Matthews, the Irish "soda-fountain king". Other residents are just as colourful, including Albert Ross Parsons, the Columbia University professor of Egyptology, whose family tomb is shaped like a pyramid.

Green-Wood Cemetery tour (001 888 606 9255; bigonion.com). Specified days. Tours cost $15.

Dead Apple Tours

The tour, in a 1960 Cadillac hearse, fondly dubbed Desdemona, takes in some of New York’s most morbidly fascinating landmarks, including the place where James Monroe, America’s fifth president, died in 1931, the buildings where the artist Keith Haring, the actor Heath Ledger and the writer Dylan Thomas spent their final moments, and the locations of rocker Sid Vicious’s and the artist, Jean-Michel Basquiat’s heroin overdoses. There’s also a grisly mobster death: the spot where “Crazy Joe” Gallo was shot while tucking into some pasta.

My far-from-morose guide, Drew Raphael, also tells the stories of the “Hangman’s Elm”, where many criminals were sent to their death in Washington Square Park. “Death is the great equaliser; it comes to us all. It’s also a fascinating subject no matter where in the world you’re from,” he says.

Dead Apple Tours (001 888 557 1312; deadappletours.com) Daily; two-hour tours cost $45.

Biking and Birding Tour

"It's a great eco-friendly way to get away from the hustle and bustle of the city and enjoy nature," says guide and naturalist Gabriel Willow, as he pedals along one of New York's extensive network of bike lanes. The NYC Audubon's Biking and Birding Tours cover about 15 miles, depending on which tour you choose. In September, Willow is leading cyclists through Brooklyn and Sheepshead Bay, along the shore and out to Jamaica Bay. Along with great views along the way, sightings should include a host of water fowl and migratory shore birds including herons, egrets, cormorants and, if you're lucky, a white pelican which has recently been spotted in the area. The other route, offered in October, leaves from the south-west corner of Central Park, at Columbus Circle, and goes over the Washington Bridge to Palisades Park in search of hawks, falcons and vultures.

Exhausted cyclists have the option of making the return journey by train. Willow says: "It's a great day out and a unique way to experience the non-human inhabitants of the city."

For more information visit www.nycaudubon.org. Biking and Birding Tours run on various dates in Sep and Oct, 9am-4pm. Tours cost $36 (not including bike hire).

Hassidic Jewish Walking Tours of Brooklyn

"Jewish people have 613 commandments to live by: from how we put on our shoes, to which side of our body we go to sleep on," says Rabbi Epstein. It's one of the many insights he shares on this tour of the Hassidic area of Crown Heights. The first major immigration of Jews to New York began in the 1880s, and most started in the Lower East Side before moving to Brooklyn.

Rabbi Epstein goes to places not normally open to the public, including the Rebbe's Library, the Chabad Lubavitch World Headquarters, and the synagogue. "This is a strong community," he says. "We want the world to understand us better."

Jewish Tours (001 718 953 5244; jewishtours.com, daily 10am). $42 including lunch.

Museum of the American Gangster

In the 1920s, 80 St Marks Place in the East Village housed one of the most fashionable illegal speakeasies in New York City. Earlier this year, the building re-opened as the Museum of the American Gangster. "During renovations in the Sixties, this maze of hidden underground rooms and $2m were found in the basement," says the museum owner and director, Lorcan Otway, indicating the remnants of dusty beer bottles and cigarette butts left behind by Prohibition era gangsters. Otway shows me a hidden passageway where alcohol was smuggled in from the street, and a back entrance which was guarded and used by those in the know to gain entry. The vast interior housed a restaurant and a 160-seat theatre where New York's most notorious gangsters and their molls would come to eat, drink and be entertained.

Frank Sinatra worked as a singing waiter here in his youth; and bizarrely, Leon Trotsky also lived in the building in 1917. "This is a fascinating building. Our job is not to glorify criminals but to objectively tell the story of the role crime, gangs and the mob played in shaping society and politics in America," says Otway.

Museum of the American Gangster, 80 St Marks Place ( museumoftheamericangangster.org). Open daily (except Wednesday), admission is $15 with an additional $5 for the speakeasy tour which is twice daily.

Governors Island

A former US army base, Governors Island lies between Manhattan, Brooklyn and Staten Island. It is still home to scores of old army buildings: barracks, a library, the officers' quarters, a former prison and two forts dating back to 1812. I arrive via the ferry with hired bikes and a picnic (there's nowhere to buy food on the island), ready to explore. As well as Park Ranger guided tours, there are events which include exhibitions, concerts, miniature golf, kite flying and stone carving workshops.

"The Native Americans named it 'nut island' because there were lots of oak, chestnut and hickory trees on Governors Island," my guide says. "The Dutch bought it from them for a string of beads, two axe heads and some nails." The strategic position of the island, which at one time had a population of 3,500, resulted in it being used as a military base by the British and Americans for more than 200 years. Recent attempts by Donald Trump to erect luxury flats have so far been denied.

Governors Island ( govisland.com). Open Friday-Sunday until October 10. There are free ferries from Manhattan's South Ferry Terminal and Brooklyn's Pier 6, Brooklyn Bridge Park, departing every hour on Fridays from Manhattan and every 30 minutes from Brooklyn and Manhattan on Saturday and Sundays. The journey takes about 30 minutes.

Staten Island Pizza Tour

"People think Staten Island and they think Mafia. My job is to challenge that view," says guide Larry Ambrosino. We will visit four of Staten Island's most celebrated pizzerias – Denino's (Mayor Bloomberg's favourite), Jimmy Max, Joe and Pat's, and Lee's Tavern. Eating is obligatory at all four stops.

A native Staten Islander, Larry loves his home and, between pizza stops, delights in showing visitors sights which don't figure on the usual tourist map, including the Carousel in Willowbrook Park and St George's Theatre (where Tony Bennett played recently and Liza Minnelli is appearing in November); the Albanian Mosque; and Grymes Hill, home to many Wall Street millionaires, which has beautiful views across to Manhattan.

Staten Island Pizza Tour (001 347 273 1257; sinewyork.org). Tours run on specified saturdays, 11am-4pm, and cost $40 including food and soft drinks. Midweek group tours cost $30.

The Atlantic Avenue Tunnel Tour

As the traffic thunders along one of Brooklyn's busiest thoroughfares, a queue of 80 intrepid adventurers disappear one by one down a manhole in the middle of the road. Underground, we're met by historian Bob Diamond, who discovered the Atlantic Avenue Tunnel in 1981, more than a century after it was sealed by authorities and forgotten about. He stumbled on references to the tunnel in historical documents and, after a 10-year search using a gas mask, chain ladder, oxygen tank and a torch, he finally found it. "A lot of what I'm going to tell you today sounds made up but I assure you it's completely real," says Diamond, before launching into a 90-minute spiel of corruption, bootlegging, murder, German spies, pirates in New York harbour and razor gangs. North America's oldest underground railway tunnel, it was finished in 1844, built by Irish immigrants at a cost of $66,000.

Atlantic Avenue Tunnel Tour (001 718 941 3160; brooklynrail.net/bhra_events.html). Next available tour 12 September. Suggested donation of $15. Sturdy footwear and a torch required. V

Stargazing on the High Line Park

"Wow, I can see Saturn," says a little skateboarder boy, his eye glued to a telescope. "That's so cool." The High Line, an elevated freight railroad dating from the 1930s, lay derelict for years until a $152m (£98m) facelift transformed it into one of New York's most popular parks.

By night it is the perfect place to gaze at the stars. Every Tuesday night, half-a-dozen experts from the New York Amateur Astronomy Association are on hand with high-powered telescopes, ready to explain the celestial wonders of the night sky to a mixed crowd of tourists, Manhattanites and intrigued passers-by.

"Gradually the night sky changes and we see different things," says organiser Joe Delfausse, explaining how visitors can expect to see Venus, Saturn, Mars, Jupiter and Mercury with varying degrees of clarity over the coming weeks.

"It's impossible not to be blown away by it," he adds. "Every once in a while someone says, 'You've changed my life forever.'" Judging by the long queue waiting to look through the telescope, Delfausse is succeeding in his mission to infect the masses with his passion for all things celestial.

Stargazing on the High Line Park ( thehighline.org/events and www.aaa.org). Free. Tuesdays from sunset till 10pm.