Ultimate weekend in Manhattan: 3-day itinerary of its greatest hits

It’s been 10 years since I moved to New York City, and I rarely get tired of its sparkle. I don’t consider myself a true local – I grew up on a cul-de-sac and took a school bus (not subway) to class – but I’ve made a home here in Manhattan, where I’ve lived in various neighborhoods over the past decade. The rent? Astronomical. The possibilities? Priceless. 

Jay-Z and Alicia Keys had it right when they called NYC a “concrete jungle where dreams are made of.” People come here to find themselves; there are endless choices, and it’s up to you to carve your own path through the beautiful chaos. The city has five boroughs, each with its own magic – Manhattan, Brooklyn, Queens, Bronx and Staten Island – but I’m going to focus on Manhattan, because if you want to see the Big Apple’s greatest hits, this is where to start.

• When to arrive: Manhattan is on 24/7, so come whenever works best for your budget. That said, regardless of destination, I like to arrive during the daytime for safety reasons, especially if I’m taking public transportation.

• How to get from the airport: You’ve got options ranging from $ to $$$. Here’s our full breakdown of how to get to and from NYC’s three main airports: JFK, LGA and EWR.

• Getting around town: Walk or take the subway. There are lots of rideshare options, but approach them with caution; surge pricing gets expensive during rush hour, late at night and during bad weather. Often traffic is so bad, it’s faster to take the train than a car.

• Where to stay: You can’t get more NYC than The Plaza – yes, from Eloise at The Plaza. (And Sex and the City and Home Alone 2!) For something less expensive but still trendy, try The Dominick or Arlo in SoHo or Midtown.

• What to pack: Your comfiest shoes. You’ll be getting your steps in.

Friday

Morning: Grab coffee and a classic New York bagel with bacon, egg and cheese at Best Bagel Coffee or with cream cheese and lox (smoked salmon) at Russ & Daughters, then go where locals avoid at all costs: Times Square, the glittering Disney World of NYC. You’ve got to see it at least once in your lifetime, and I recommend getting there as early as possible to beat the crowds. If seeing a Broadway show is on your bucket list, line up at the TKTS booth there for last-minute discounted tickets.

How to spend the day: Next, skip going up the Empire State Building and instead head east to Summit One Vanderbilt, a newer skyscraper that gives you sweeping city views plus immersive art installations. It’s connected to Grand Central Terminal, which is worth a stroll – look up at the ceilings! – and has a food court with lots of lunch options.

If you’ve got time to spare, take the 4 or 5 express subway to the Upper East Side and see a bit of The Metropolitan Museum of Art. You could easily spend a whole day there, but even wandering around for one or two hours is worth it.

Dinner: If you like sake and Japanese small plates, make a reservation at Sakagura – a secretive restaurant and bar below an average midtown office building that you’ll miss if you aren’t looking for it. For fine dining in the area, try the French-inspired seafood at Michelin-starred Le Pavillon.

After dark: Downtown is where the party’s at. Bar hop through East Village – start on St. Mark’s Place – or sip cocktails on a swanky rooftop bar in Lower East Side. Either way, your night will likely end with a $1.50 slice of pizza. (Some places still offer 99-cent slices, but many increased prices due to inflation.)

Saturday

Morning: Brunch is your best friend. Skip Jack’s Wife Freda – ever since it got popular on TikTok, the lines have been insane – and go to Two Hands, an Australian cafe with hearty but healthy dishes. (Order the ginormous banana bread for the table!) Their TriBeCa location is easier to get a table at and is across the street from two artistic gems: 56 Leonard Street or “Jenga Building” (a skyscraper of overlapping condos) and Anish Kapoor’s new silver reflective sculpture that’s basically an NYC version of his Cloud Gate (“the bean”) in Chicago.

How to spend the day: Go to the West Side Highway, which runs along the left side of Manhattan and is more spacious than The High Line, and stroll or bike down its path toward One World Trade Center, gleaming in the distance. In my opinion, you can skip One World Observatory if you’ve already gotten your fill of birds-eye views, but definitely make time for the 9/11 Memorial and Museum. It’ll be an emotional visit, so bring tissues.

Then stop by The Oculus, an architectural masterpiece inside and out, and pick up lunch at Gansevoort Liberty Market, which has everything from tacos to sushi. Keep going south to Wall Street to see the New York Stock Exchange and famous Charging Bull Statue. (Expect to wait in line if you want to take a photo with it.)

Dinner: If the weather’s nice, get a pint and standard bar bites on Stone Street, where the bars spill out onto the cobblestone street. For more of a sit-down experience, try historic Fraunces Tavern or Dead Rabbit. Round out your downtown sightseeing at The Battery, a park on the southern tip of Manhattan where you can see the Statue of Liberty from afar (and for free!) as the sun sets. It’s got a gorgeous SeaGlass Carousel that both kids and grown-ups will appreciate.

After dark: Assuming you’ve checked out the east side on Friday night, go out in West or Greenwich Village on Saturday. Here, you’ll find lots of gay and lesbian bars, especially near Stonewall Inn, where a 1969 riot kicked off the LGBTIQ+ rights movement. There’s also a mix of casual pubs, upscale lounges, jazz clubs and speakeasies. Katana Kitten is a popular pick for cocktails – you’ll need a reservation – or go to Cellar Dog for live music and shuffleboard, ping-pong and billiards.

Sunday

Morning: Start with coffee and a cronut (half croissant, half doughnut) at Dominique Ansel Bakery, then get ready to shop till you drop in SoHo. One of the many convenient things about living in Manhattan? Most brands, even direct-to-consumer ones, have a pop-up or brick-and-mortar store here. If there’s something you’ve been eyeing online, you may be able to buy it in real life. But if you’re just window shopping, I recommend sticking to streets on either side of Broadway, where the sidewalks are less congested.

How to spend the day: Once you’re shopped out, take the subway uptown to Central Park for a leisurely walk or bike ride. Bonus points if you bring snacks for a picnic, but you can also grab a hot dog from street vendors like Nathan’s Famous. There’s lots to do in NYC’s most famous green space, but if you only see one thing, make it the Bethesda Terrace with its stunning fountain. For something more active, rent a rowboat and get out on the lake. 

Dinner: If you end your Central Park adventures on its west side, you can subway down to Hudson Yards to see the Vessel. You can’t go up it anymore, but it’s still worth walking through the plaza on your way to Little Island, a floating park that opened in 2021. Stop by Chelsea Market first and order tacos to go from Los Mariscos or Los Tacos No.1, then eat them on the lawn while you watch the sunset over lower Manhattan on your final night.

You won’t have seen it all, but you’ll have seen enough to know how quickly you want to come back to see the rest.