Unfinished business: A second-timer’s guide to New York City

written by Doug Whyte March 12, 2018
Manhattan Bridge as seen from DUMBO, New York

Nothing compares to your first time in New York. The Empire State Building, the Brooklyn Bridge, Times Square, Katz’s Deli – the memories go on and on.

The trouble is, New York is huge. There’s just so much to see and do that it’s impossible to experience all the city has to offer your first time around. But this is what second-time visits are all about.

Now that you’ve ticked off the bucket list items, it’s time to sink in. From exploring different parts of the city to digging deeper into the food scene, here’s how you can tackle your second visit to the Big Apple.


Find your favourite neighbourhood

Street art in Williamsburg, New York

Leonard Zhukovsky/Shutterstock

On your first trip to New York, you might have stayed in Times Square or somewhere else in Midtown. Granted, this puts you smack bang in the middle of the action. But for your second time around, you’ll likely want to branch out a little.

Keeping it to Manhattan and Brooklyn is still a good tactic, but there are plenty of other neighbourhoods to stay in or visit. In Brooklyn, Williamsburg is where you’ll get your fill of second-hand shopping, arthouse cinemas, hipster coffee joints, and trendy restaurants. The same can be said of Greenpoint, Bushwick, and to a more relaxed extent – Clinton Hill.

In Manhattan, staying in the Lower East Side or East Village provides a great base to explore the rest of the city. Just be warned – the restaurants, art galleries, museums, and high-end shops will easily hog your attention. When you finally do break free, head to other Manhattan favourites such as Chelsea and Harlem.


Leave it all behind

Entrance to Luna Park on Coney Island

Christian Mueller/Shutterstock

Even for locals, there’s enough going on in New York to sustain you for years. But there comes a time when the chaos and crowds get to you. So why not leave it all behind for a day?

If you’re not up for going too far, Coney Island is a good first step. You could also explore other Long Island destinations such as Stony Brook and Port Jefferson, go for a hike in Cold Spring, or even ride the train to Philadelphia.

For something truly special, escape up the Hudson and visit Dia:Beacon – a contemporary art museum housed in a former printing plant, around 60 miles from Manhattan. The exhibitions are site-specific, the views of the river are epic, and the small town vibes of Beacon are downright charming.

Make a meal of it

Fresh Italian pizza in New York City pizzeria window


There’s no shame in orbiting your days and nights around eating. In fact, New York absolutely caters to this. With the main tourist activities out of the way, you’re free to choose a different breakfast, lunch and dinner spot every day – repeating the ritual in a wonderfully indulgent cycle.

Why not bring alternative tourist activities into the mix? Combine lunch at Chelsea Market with an afternoon walk on the High Line. Take in Manhattan views from DUMBO before feasting at Shake Shack. Enjoy a bagel at Russ & Daughters with a side of shopping in SoHo. Wander Manhattan’s Chinatown on a belly full of cheap treats from Vanessa’s Dumpling House. The combinations are endlessly delicious.

While you can get decent food all over the city, the pick of the neighbourhoods would have to be the Lower East Side, East Village, Williamsburg, and if you’re up for it, Flushing in Queens.


Under-the-radar arts and culture

The Tenement Museum in Lower East Side, New York

DW labs Incorporated/Shutterstock

During your first visit to New York, you have to see a Broadway show. You have to go to MOMA. You have to explore the Met and the American Natural History Museum. In fact, these are things to do or your second, third, fourth and fifth visits too.

But what about the Tenement Museum in the Lower East Side? Or the art galleries in Chelsea? The good news is, if you’re short on time and looking for alternative cultural experiences, there’s plenty to keep you occupied.

When it comes to lesser-known stages, see a production at the Signature Theatre, Ars Nova, SoHo Playhouse, UCB Theatre, or Joe’s Pub – you’ll find there’s much more going on off-Broadway (and off-off-Broadway) than there is on Broadway.

New York is also the sharpest, most scathing, and totally hilarious city in the world. So if you didn’t go to a comedy night on your first visit, make it a priority. The big names include The Comedy Cellar, The Stand and Caroline’s on Broadway, but there are also a string of smaller places to check out, such as Littlefield and The Creek & The Cave.

In Brooklyn, a fun thing to do is see a movie at the Alamo Drafthouse or Nitehawk Cinema. While both show a range of independent films and blockbusters, the real treat is the in-cinema food and drink service. At Nitehawk, get the pizza popcorn with truffle butter, oregano, Parmesan, pepperoni and chilli flakes – don’t think, just do it.

Everyone’s second time in New York is different. Some people like expanding their experiences, while others prefer seeing the big sights from a different angle. Some enjoy having no plan at all – it all depends on what you’re interested in and how you like to travel. But, if you’re really stuck for ideas, just take inspiration from this article.

Explore New York City and beyond on an Intrepid tour of the United States, check out the full range here

Feature image C/O Christian Mueller.

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