There are so many ways to explore — and gain an understanding of — a city that just won’t stop evolving, innovating and piling on new things to do and see. Which is to say that if you’ve visited New York City in the past, your next visit will be different — and we’d like to make it better.
The trick is to define the neighborhoods that are home to the attractions on your list, then plan on walking the streets, so you can discover the boutiques, bars, restaurants and other venues along the way. No, you won’t see it all, and your legs will tire. But there are cafés for that, where the people-watching is well worth the (fair warning!) sometimes steep prices charged.
As always, check for travel restrictions and closures before planning your trip.
Friday: Meet the Icons
Start by seeing the city from up high; the bird’s-eye view makes for an outstanding orientation to the city’s layout. Fortunately, New York has never had more options for sky-high views, but many critics are crowning the newest — Summit One Vanderbilt, next to Grand Central — as the winning experience.
Three levels of windows and mirrors, a glass elevator and transparent-floor boxes jutting out almost 1,110 feet above the city offer ethereal eye candy, as well as endless selfie ops. Got your bearings? Good.
Walk less than a mile up Fifth Avenue to that large lawn you ogled from on high. Central Park doubles as a famous attraction and the city’s backyard, a lush haven for locals and visitors alike. Surprises abound — the park has a peach tree! — and there’s slightly more solitude than you’ll find on the surrounding sidewalks.
Seek out the Hallett Nature Sanctuary, four of the park’s prettiest acres that teem with birds, rabbits, turtles and other critters. Chill on one of the branch benches and take in the triptych of water, treetops and skyline.
On your way out of the park, along Central Park South, is the Art Deco JW Marriott Essex House, a classic that’s now home to the buzzy Southgate Bar & Restaurant, where you can rest over lunch, a snack or a spirited beverage.
Whether or not you think Campbell’s soup cans qualify as art, America’s best collection of modern masterpieces is a can’t-miss: MoMA boasts a rotation of nearly 200,000 works in every imaginable medium. Lesser-known artists mix with the famous names (Van Gogh, Kahlo, Dalí, O’Keeffe and — yes — Warhol) to create an energetic, almost playful space.
Nab a Theater District seat — whether it’s for a musical extravaganza or a classic drama starring one of the world-renowned actors and actresses who regularly grace these stages. The TKTS booth in Times Square offers discount seats.
For a late-night bite after the show, try the French fare at Café Un Deux Trois, a Times Square mainstay since 1977; or check out Restaurant Row, on West 46th Street between Eighth and Ninth avenues.
Saturday: Make a Borough Break
Your destination today is the former Dutch community of Breuckelen — now, of course, Brooklyn — which has maintained its robust pockets of international diversity while stealing Manhattan’s thunder as the heart of city cool.
Take a walk over the East River on the Brooklyn Bridge, from downtown Manhattan to the Brooklyn neighborhood of DUMBO. Get a dose of inspiration as the suspension wires of this neo-Gothic marvel appear to dance and morph as you cross.
Head to Brooklyn Bridge Park and gaze across at the towering Manhattan skyline as the river laps at the shore. And hold onto that view as you hop on the glass-enclosed Jane’s Carousel, a 1922 painted horse parade that’s been restored to its full majestic glory.
Explore a different kind of transportation at an under-the-radar gem that’s also underground. The New York Transit Museum serves up a sepia-toned vision of the city in an old subway station. Check out vintage subway cars, buses and tokens (turnstyles weren’t always digital!), and delight in imagining a rich mix of people straphanging their way through the 20th century.
Head from Downtown Brooklyn to the revitalized neighborhood of Crown Heights to taste the city’s cultural mash-ups. And what better place than a Yemeni Muslim-run Jewish deli in an Afro-Caribbean neighborhood? That’s exactly what you’ll find at David’s Brisket House; order (what else?) the pastrami piled high on rye.
Wind down at the Brooklyn Navy Yard, a few miles northwest of Crown Heights. Among the many small businesses there is Rooftop Reds, the world’s first commercially viable urban rooftop vineyard — yes, vineyard — open March through November, where you can sip with a view. And year-round, the nearby Kings County Distillery pours its award-winning whiskeys in a hip, 19th-century space.
Sunday: Embrace the Wander
Today, wind your way down to Manhattan’s tip, starting by strolling south along the High Line from its northernmost entry at West 30th Street. A prime example of urban evolution, this elevated railroad turned walkway is lined with lush gardens, public artwork, snack options and yet another unique view of the city landscape.
Hop off for any last-minute shopping — and loads of lunch options — at the many shops in Chelsea Market. Then head to the West Village and put your phone away; this neighborhood was made for aimless ambling. Lose yourself along the cobblestone streets, traipsing past 18th-century town houses and keeping an eye out for the occasional celebrity.
Get in line with locals to grab a slice at New York institution Joe’s Pizza and decide for yourself whether it’s truly the city’s best. Then make your way to Bleecker Street, listening for any lingering tones of Dylan or poesy of Poe. Check in on local favorites like Faicco’s Italian Specialties market or the Ottomanelli Bros. butcher shop, which carry the torch of this area’s Italian heritage.
Finish up in the Financial District, where a literal wall from the 17th century has evolved into the aptly named Wall Street. Pay your respects at the National September 11 Memorial & Museum, with an open-air plaza centered on a stunning yet somber installation engraved with the names of the people who lost their lives in the tragedy.
The Oculus building is just as arresting, with its soaring white metal ribs, designed to resemble outstretched fingers releasing a dove. It sits atop an enclosed public space (and transportation hub) filled with fancy shops and restaurants. One to check out: Everyone loves Eataly for its maze of small Italian eateries, wine bars and cafés.
End your weekend at Battery Park, in the shadow of the shimmering One World Trade Center, gazing out at the Statue of Liberty. You’ll be at the very tip of Manhattan, where the Hudson and East rivers blend to become New York Harbor.
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