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The Best of The Big Apple: A Three Day Itinerary for First-Timers in New York City

Think it’s impossible to hit all of New York’s highlights in just three days? Guess again. This weekend-long itinerary will show you the best of the best without any long lines or overhyped attractions.

DAY 1 – UPTOWN

Start off by fueling up on bagels and lox at an Upper East Side hidden gem, Sable’s Smoked Fish (1330 Third Ave, open daily 8:30AM-6:00PM). After a quick stroll past decadent townhouses and lavish galleries, arrive early to beat the infamous lines for The Metropolitan Museum of Art, the most visited museum in the western hemisphere. 

File:MET NYC.jpg - Wikimedia Commons

Browse global treasures and ancient artifacts to your heart’s content, then journey westward through Central Park, where you can enjoy panoramic views atop Belvedere Castle, get lost in the woodsy maze of The Ramble, or simply hit a hot dog cart and people-watch from one of the park’s 9,000 benches. 

new york city :: belvedere castle | Mehr über dieses Fotos g… | Flickr

When you exit at West 77th St, you’ll be awestruck by the iconic facade of The American Museum of Natural History, where it’s time to take a dive deep into millions of years worth of natural wonders. Head up Amsterdam Ave through the heart of the Upper West Side until you reach the largest church in the country, The Cathedral Church of St. John the Divine, where a self-guided tour can be done in a matter of minutes. 

Continue along Broadway through Morningside Heights, where Seinfeld fans can take that obligatory selfie in front of Tom’s Restaurant, and academia enthusiasts can meander Columbia University’s pristine campus. Next stop is the ever-tranquil Riverside Park, where you can pay your respects at Grant’s Tomb (122nd and Riverside Dr) or admire the facade of the nation’s tallest church, Riverside Church.

File:Toms Restaurant (7319156568).jpg - Wikimedia Commons

Build up an appetite on your way through Harlem, where picturesque rows of brownstones give way to world-famous landmarks like The Langston Hughes House and the legendary Apollo Theatre, which has showcased local and international superstars since 1913. Finish off the day by experiencing the best soul food New York has to offer at Amy Ruth’s, followed by a world-class performance at the historic Minton’s Playhouse, where legends such as Charlie Parker and Thelonius Monk revolutionized the sound of modern jazz. 

Amy Ruth's - Front | A Harlem "staple" known for its fried c… | Flickr

DAY 2 – MIDTOWN

The second day begins at a quintessential all-American diner, John’s Coffee Shop, located a block away from the United Nations building, where a guided walking tour offers an immersive journey through the epicenter of international peace and diplomacy. Afterwards, enjoy river-to-river views down 42nd Street as you’ll pass Clark Kent’s fictional office, the Daily News Building and the crown jewel of the Art Deco era, The Chrysler Building. Absorb the hustle and bustle of the world’s most famous train station, Grand Central Terminal and enjoy a leisurely lunch at its iconic Oyster Bar

File:NYC - Chrysler Building - 0612.jpg - Wikimedia Commons

Next, take in some quietude as you browse through millions of books at the grandiose New York Public Library, followed by coffee and prime people-watching at the adjacent Bryant Park. Resist (or give into) the urge to shop for designer brands as you head north along Fifth Avenue. Poke your head into Saint Patrick’s Cathedral for inspirational eyefuls of gothic architecture and exquisitely detailed stained glass windows. Across the street, marvel at the dramatic heights and old-world charm of Rockefeller Center

The energy levels ramp up drastically two blocks westward, as you enter the crossroads of the world, Times Square, a landmark so bright, it can be seen from outer space. 

Times Square, NYC | Since Times Square is such an intense pl… | Flickr

Nearby in Hell’s Kitchen, global flavors blend seamlessly with the city’s gritty past, as a plethora of pre-theatre dining options can be found along Ninth Avenue and Restaurant Row. For authentic Taiwanese cuisine, fill up at Four Four South Village (368 West 46th St, open daily 11:00AM-10:45PM). 

No trip to Gotham is complete without the glitz and glamour of Broadway. With 41 theaters to choose from in the Theatre District, The Lion King at Minskoff Theatre retains its status as the most popular. For the ultimate nightcap, head a few blocks south and soak up some expansive skyline views at Skylark Rooftop Lounge 

The Lion King on Broadway at the Minskoff Theatre | Loren Javier ...

DAY 3 – DOWNTOWN / BROOKLYN

After a memorable morning coffee under the vaulted ceiling of the iconic Woolworth building’s Five & Dime, walk a few blocks alongside City Hall Park to rent a bike from Unlimited Biking (79 Chambers St, open daily 9:00AM-5:00PM). 

Why You Need to Bike Across the Williamsburg Bridge

Whiz past lower Manhattan’s greatest hits on two wheels, catching awe-inspiring glimpses of Saint Paul’s Chapel, the oldest building in Manhattan, Trinity Church (site of Alexander Hamilton’s Grave,) Zuccotti Park (location of 2011’s Occupy Wall Street movement), and the World Trade Center campus, complete with views of The Oculus, 9/11 Memorial Pools, and One World Trade Center, the tallest building in the western hemisphere. 

Make your way to the postcard-worthy Charging Bull statue, past the landmark New York Stock Exchange, and into South Street Seaport, where you can hop aboard cargo ships from the 1800s and admire Brooklyn’s skyline from across the East River. 

NYC - Bowling Green: Charging Bull | Charging Bull, sometime… | Flickr

Make your way through the vibrant streets of Chinatown and over the Manhattan Bridge, where you’ll indulge in world-renowned brick oven pizza at Grimaldi’s. Cycle the idyllic streets of America’s first suburb, Brooklyn Heights and back over the Brooklyn Bridge, where you’ll be wonderstruck by sweeping views of the Statue of Liberty, Ellis Island, Staten Island, and the entire Manhattan skyline. 

File:View of Brooklyn Bridge Park from Manhattan Bridge (cropped ...

After returning your bike, hop on the subway for a few stops and visit the Lower East Side’s Tenement Museum for an eye-opening look into the lives of 19th century immigrants. Afterwards, meander through the East Village’s kaleidoscope of ethnic enclaves, the Puerto Rican Loisaida, Ukrainian Village, Little India, Little Tokyo, and finally Greenwich Village, with its multitude of entertainment offerings: The Bitter End, where legendary acts such as Bob Dylan and Lady Gaga started out, The Comedy Cellar, an alma mater for stand-up icons like Robin Williams and Chris Rock, or the West Fourth Street Courts, where NBA stars Stephon Marbury and Anthony Mason were discovered. 

Round out the day at Minetta Tavern, where the burger is as famous as its star-studded clientele, and finish up across the street at The Up and Up, an elegant speakeasy with the ideal ambience for reflecting on a perfect three days in New York City. 

Macdougal Street, Greenwich Village | A row of shops and res… | Flickr

What do you think, is there anything we missed on this Three Day Itinerary of New York City? There is so much to take in when visiting it’s almost impossible to fit it all in just three days.

If you need help getting around, theres no faster way than biking in this urban jungle. Visit https://unlimitedbiking.com/ for guided bike tours and rentals during your stay. And happy cycling!

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