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A New York Itinerary: 4 Days in the City that Never Sleeps

Make the most of your trip to New York with this carefully curated guide to the city


Road in Greenwich Village, New York

Planning a trip to NYC? Thanks to this expert New York itinerary for 4 days, all you have to do is remember to book your flights. Oh, and book your favourite Plum Guide home. In this itinerary, you'll see first-hand the efforts that we here at Plum Guide go to to guarantee you a trip to remember, so read on for our expert advice on how to spend 4 days in the Big Apple.

Day 1: Wander round a museum before climbing the Empire State Building

Wake up and smell the coffee. Grab one from your local bodega and caffeinate in the open air with a stroll or cycle through Central Park. For those crazy admirable fitness buffs who like to exercise on holiday, consider this your workout for the day.

Then it’s off to Sarabeth’s on Central Park South for a filling American breakfast before you head to a museum. The Met, Guggenheim, MoMA and American Museum of Natural History are all within walking distance so pick your poison - sorry, we mean museum - and soak up some of New York’s most thrilling cultural hotspots. For those of you who don’t enjoy staring at art and artefacts all day, consider that you’re getting it out of the way on day one. You’re welcome.

The Guggenheim Museum, New York City

While in Midtown Manhattan, other worthwhile sights to see include The New York Public Library (SATC fans, this is the spot where Mr. Big failed to marry Carrie - rude), Grand Central Terminal (because we know a lot of you are really into trains) and St. Patrick’s Cathedral, New York’s own neo-gothic cathedral that dates back to 1879 (ancient, by US standards).

Now it's time to head to the Empire State Building. Get there in time for sunset and take in the views from 381 metres up. Then it’s off for a classic steak dinner at the iconic Smith and Wollensky. If by this point you are failing to remember that you’re too old to keep drinking after dinner, make your way to The Rum House, a swanky piano bar in the Edison Hotel for classic cocktails and a lovely prelude to tomorrow’s hangover.

The Wizards of Central Park, Plum Guide home in New York

Day 2: Visit the Statue of Liberty before seeing a Broadway show

Start as you mean to go on this morning, with a breakfast at Clinton St. Baking Company. Their pancakes are the best in the city, so show up with an appetite. (If that means you have to go to the private gym in your building beforehand, then you do you).

Now it’s off to the Statue of Liberty and Staten Island where you’ll live out the American fantasy you remember from the films of your childhood - yes, you are that old. It might seem is cheesy, but there's also something special about this tour…and the photos of the skyline from the water simply can’t be beat. The 9/11 Memorial and Museum is a moving and educational possibility for afterwards, or go for a walk along the High Line, a meticulously designed elevated park that spans across an out-of-use railroad track.

If you’re hungry again, snack on some street food from Chelsea Market or a soft-serve ice cream from Milk Bar before spending the rest of the afternoon shopping and gallery hopping around the neighbourhood.

Tonight you’re headed to the theatre because, well, a Broadway show is somewhat compulsory within a New York itinerary of 4 days. What else are you going to bore your friends with stories about for the next year? Take in Times Square in all it’s illuminated glory before sitting down to the latest critically-acclaimed play. Dinner will be at snug post-theatre classic Joe Allen where Broadway patrons and actors have been enjoying comfort food and cocktails since 1965.

Starburst, Plum Guide home in New York

Day 3: Spend an enjoyable day in Brooklyn

It’s day three of your New York itinerary so stop acting like a tourist (not that you ever would, surely?) and swap Manhattan with Brooklyn for the day. If you’re in the mood for a quiet and laid-back atmosphere, walk across the Brooklyn Bridge and spend the day in Brooklyn Heights. The Brooklyn Museum and Brooklyn Botanic Garden are nearby if you just need to have an activity planned. For lunch, head to Henry Street, home to loads of great lunch spots.

Brooklyn Bridge, New York City

If you’re the type to drink acidic black Americanos and wear beanie hats in the summer - skip Brooklyn Heights and opt for Williamsburg instead. Walk across the Williamsburg Bridge and spend the day exploring this neighbourhood that is now more expensive than Manhattan. Try chicken and waffles for lunch at Sweet Chick or head to the eight-seater hidden gem Mexico 2000.

After a lovely day in BK (that's Brooklyn, by the way), head back to Manhattan for drinks at swanky and comfortable Upper East Side bar The Auction House, followed by a tremendous French dinner at Daniel. Their prix-fixe meal is a bucket list experience, but if you prefer a more relaxed option, order à la carte in the lounge.

Wooden Garlands, Plum Guide home in Brooklyn, New York

Day 4: Head to Greenwich Village and SoHo

A New York itinerary of 4 days wouldn’t be complete without spending a day in Greenwich Village and SoHo. Start with a takeaway breakfast from Tompkins Street Bagels, then walk to Washington Square Park where you can sit and enjoy your food in what was once Jean Michel Basquiat’s preferred hangout.

There are lots of great independent bookshops, boutiques and cafes dotted around the Village so take your time as you stroll the streets living your best Allen Ginsberg fantasy. Enjoy lunch at classic SoHo French bistro Raoul’s or keep it authentic with a pastrami sandwich from no-frills Lower East Side deli, Katz, serving hungry locals since 1888.

And to mark the end of your New York itinerary in style, it’s off to the Fat Cat for drinks and ping pong followed by a knockout Italian dinner at Bar Pitti. As you dip your spoon into creamy tiramisu and look out the window at the passerby on 6th Ave., you’ll start planning your next trip before you even finish your mouthful.

The Swiss Army Knife, Plum Guide home in New York

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