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New York Itinerary: 5 Days in the City that Never Sleeps

Our curated New York itinerary guarantees five days of family fun in the Big Apple


Prospect Park, Williamsburg, New York

Heading to the Big Apple for five days of city shenanigens? Start spreading the news because with this New York itinerary: 5 days, your trip will be planned to absolute perfection. Here at Plum Guide, we do all the hard work for you, so all you have to do is simply follow our expert advice and have the trip of a lifetime.

Day 1: Explore Greenwich Village and enjoy a Broadway show

It’s the first day of your itinerary so wake up, roll out of bed and take in the killer view from the luxury NYC apartment your lifelong hated job hard work has paid for. Start with a quick stroll to what is New York’s most famous skyscraper, the Empire State building. If you don’t mind rising early, book a sunrise ticket and watch Manhattan wake up before your eyes.

Next it’s off to Chelsea and the High Line. Enjoy a lazy stroll through this elevated park and grab a sumptuous breakfast from Chelsea Market when you get nibbly. Spend the rest of the day living the 1960’s starving artist fantasy we know you have by exploring Chelsea and Greenwich Village. When evening comes, head to Times Square to take in the lights before sitting down for a Broadway show followed by a post-theatre dinner at the classic Joe Allen.

Mystical Magic, Plum Guide home in New York

Mystical Magic, Plum Guide home in New York

Day 2: Wander round a museum before ordering a fancy lunch

Start with a walk through Central Park with a traditional NYC bagel in tow. If you’re staying in an Upper West Side apartment, grab yours from Absolute Bagels. Now, you can’t ask for a New York itinerary (5 days) and not expect to be visiting at least one art museum -not sorry- so this morning is all about MoMA (for modern and contemporary art) or The Met (for a more classical experience). Next up, reward yourself with a truly fancy lunch at The Grill, located in the mid-century Seagram Building.

For those who want to keep feeling arty, check out the Guggenheim Museum, Frick Collection and Whitney Museum after lunch. Otherwise, double check you’re packing your most accommodating credit card and get ready for a serious 5th Avenue spending spree. (Because you simply cannot go to New York without spending at least some time shopping in the city.) While in Midtown, be sure to step into the glorious lobby at the Plaza Hotel and make a visit to Rockefeller Center. If you still can’t get enough of yesterday’s Empire State view -or you're simply a huge 30 Rock fan- make your way to Top of the Rock for sweeping views of Central Park and downtown. Tonight go for sushi and people watching at Catch where beautifully dressed locals convene to enjoy spicy tuna and a fabulous bar.

Operation Gold, Plum Guide home in New York

Operation Gold, Plum Guide home in New York

Day 3: Head to Brooklyn for a spot of shopping

It’s the third morning of your five-day New York itinerary and you still haven’t been to Brooklyn (unless of course you’ve decided to stay there). It’s time to remedy this mishap before you have to go home and tell your friends you aren’t cool enough to leave Manhattan - see, we always look out for you. Do you enjoy farmers markets brimming with organic produce, indie boutiques and cute cafés where local families grab brunch before heading out for a wholesome walk? If so, head to down-to-earth Park Slope. Pick up lunch to-go and enjoy a picnic in Prospect Park. Admire the babies and brownstones this neighbourhood is known for and kick back with a little shopping and greenery.

Are you more of a hipster type? Williamsburg is the vibey, street-art filled, show-off-my-new-limited-edition-trainers place for you. Grab a delicious arepa (tasty South American stuffed flatbread) from the dimly lit Caracas Arepa bar and don’t miss dessert: a swirl of cereal milk flavoured soft-serve from Milk Bar (trust us). You’ll love the unique shopping and your kids will (also) thank you for the Instagram-worthy photo opps. After a long day, head to Smith and Wollensky for the ultimate steak dinner.

The Yolk House, Plum Guide home in New York

The Yolk House, Plum Guide home in New York

Day 4: Discover the city's impressive sights

Staying in a Lower Manhattan apartment? Enjoy a stellar breakfast at Clinton Street Baking Co, then live your own American Dream with a boat ride tour to the Statue of Liberty. But don’t get too excited, when she says to give her ‘your tired, your poor, your huddled masses yearning to breathe free,’ she definitely doesn’t mean you, no matter how exhausted you are having to corral your entire family around the city that never sleeps. After locking eyes with Lady Liberty, the 9/11 Memorial and Museum is a moving next stop. And for those of you who still want more great views of the city -it’s ok, we forgive you- consider the One World Trade Center Observatory.

When it comes time for dinner (and please remember you didn’t come all the way to New York to just keep eating what you normally consume at home) make your way to Atoboy where you’ll enjoy mouthwatering modern Korean small plates. From there, it’s a quick cab ride uptown to The Carlyle Hotel, where you’ll listen to live jazz and drink martinis until you absolutely must make your way home. This is the city that never sleeps, so no New York itinerary (5 days) would be complete without a chic late night.

Bricks & Glitz, Plum Guide home in New York

Bricks & Glitz, Plum Guide home in New York

Day 5: Visit Beacon, NY, and sample a range of drinks

Take a break from city life and enjoy something your friends didn’t think of doing on their trip here - a day trip to Beacon, New York. This quaint, walkable city boasts great eating, drinking and Dia: Beacon, a museum of art from the 1960’s to the present that right on the banks of the Hudson River. If drinking is more up your street than Dan Flavin light artworks or Louise Bourgeois spiders, it’s off to Denning’s Point Distillery where you can sample tantalising whiskey, bourbon, gin and vodka. Just remember to take it slow, we both know you’re not in college anymore. Watch the sunset at Long Dock Park and take in the magic of the light dimming over the Hudson before making your way back to Manhattan. An early dinner at Minetta Tavern means your last meal of this holiday will also be the best burger of your life.

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