City Guide, New York City, Travel, USA

What To Do In New York – A 5 Day NYC Itinerary

Kyroshtravelscom NYC Header

New York has been on our bucket list for many many years, and after travelling around Asia and Europe, we decided it was time to tick it off. Even with 10month old travelling with us half way around the world, we were ready to take on the big apple.

New York City has it all, the concrete jungle where dreams are made of. The hustle and bustle of this modern metropolis can sometimes be overwhelming especially coming from Melbourne, Australia. But we loved it, it’s all part of the experience!

New York has something for everyone, from modern art galleries to neighbourhoods of Brooklyn and Harlem. We have put together a 5 day NYC itinerary with what we believe the best of New York. If you don’t have five days, then feel free to cherry pick your fav things to see and do, and create your own two or three day New York itinerary.

For more about New York’s Best place to eat, CLICK HERE to read our best place to eat in New York City

The Ultimate 5 Day New York City Itinerary

Day 1 –The High Line, Chelsea Markets, Washington Square Park and Shopping in SoHo

⇒ Optional: Sunset Helicopter Tour over New York

⇒ Areas: Meatpacking District, West Village and SoHo

KyroshTravels - The High Line.png

Stop A – The High Line – 

We stayed right near Time Square and decided to catch an Uber to start point of The High Line. which on the Hudson River end of W34th Street. We started early around 8am to beat the tourist rush.

The start of The High Line has some magnificent views overlooking the Hudson River into New Jersey. Take some time out to sit in one of the big benches to “let the world go by”. On the opposite side was the Hudson railway yards for any avid train hobbyists.

The High Line walk is easy, winding through tall buildings and crossing some roads. There are lots of sculptures and other art works along the walk. Towards meatpacking district area, few street performers, who are so talented. Take a few moments to support and listen to these amazing artists.

This was one our NYC highlights, we loved it. We did the full walk from start to finish and if we had more time, we would have love to come back at night to see the different atmosphere.

Stop B – Whitney Museum of American Art –

This area is well known for its amazing art galleries and studios. We decided to pop into the Whitney Museum, which was a stones throw away from the end of our High Line Walk. Some of the other favourites around the area are:

Pace Gallery –

Cheim & Read –

Gagosian –

Mary Boone –

Barbara Gladstone –

Paula Cooper – - Chelsea Markets, New York City – Chelsea Markets, New York City

Stop C – Chelsea Markets –

After the long walk and strolling amongst some of the finest art galleries in New York, like us you would have built up a great appetite. Chelsea Market, is the perfect stop for break and to try some delicious food. This place has such an electric atmosphere, you can walk around all the unique shops or grab something to eat.

Check out our Top 10 Best Places to eat for more suggestions.

Our Favourite vendor was Los Tacos No.1. It was simply some of the best tacos i have ever eaten (We haven’t been to Mexico!)

If nothing grabs your attention, across the road from Chelsea market is another unique Food Hall – Gansevoort Market Food Hall (Stop D)

Stop E – Magnolia Bakery (Sex and the City – TV Show)

Some of you might know it or some of you might be the biggest fans of the late 90’s TV series Sex and the City. But whether you are are fan or not, this is must try bakery for any sweet tooth. The hot favourite is the banana pudding, but really anything from this bakery is totally delicious.

Stop F – Carrie’s Apartment from “Sexy and the City” TV Show

Continuing with the “Sex and the city” theme just around corner from the Bleecker Street Magnolia Bakery is Carrie’s Apartment that was featured on the show. Please note its now a private residence so tourist aren’t encouraged to loiter around. But the official address is 66 Perry Street, New York

Stop G – F R I E N D S  TV Show Apartment

Another great TV show that was filmed in this great city, FRIENDS was the one of the most watched TV shows in the late 90’s and early 00’s. Most of the locations on the TV shows can be found around New York City. Follow the crowds and relive the 90’s.

Stop H – Washington Square Park

Described as the unofficial town square of the village, a photogenic quadrangle of park space that’s bursting with energy – impromptu music jams, spirited political debate and giddy student chatter.

Feel free to bring a picnic rug and enjoy the sunshine under the trees. Feel the energy of this amazing place.

Stop I – Shopping in SoHo

Most of us have heard of SoHo neighbourhood and to be there in real life to see the modernised apartments and high end shopping felt surreal. All the top designer brands can be found walking through the streets, but there are so many independent shops that offer some great items that you won’t find anywhere else. If you are like us, and just like the window shopping, well thats totally fine as well.

Sunset Helicopter Tour over New York City

Kyrosh Travels - Sunset Helicopter Tour

This was my WOW moment for the New York Trip! I think this picture taken from my Iphone X sums it up. I flew by myself as Kylie was happy to have her feet on the ground. There were two Sunset flights offered by FlyNeon a 20min fly by over lower manhattan and the 30min flight which not only takes the lower manhattan but goes all the way to central park, empire state building and Times Square. For me the best and the scariest bit was having the doors open on the helicopter. It does get cold but the experience was once in a life time for me.

I loved the Fly Neon experience, only negative was the 35min drive to Kearny, New Jersey as that departure point. There are few other companies that offer departure from Downtown Manhattan Helipad.

Approx. Pricing – USD $275 for 15-20min flight and USD $399 for 30min

Fly Neon –

Helicopter Flight Services –

Kyrosh Travels - Sunset Helicopter Tour 2


Day 2 – Times Square, Big Bus Tour, Top of the Rock & Empire state building

Option – Basketball game (in season)


Day 3 – Chinatown, Financial District, 9/11 Memorial & Museum & World Trade Centre

Option – Broadway show and Times Square at night


Day 4 – New York Library, 5th Avenue, Grand Central Station and Central Park 

Option – Baseball game


Day 5 – Statue of Liberty, Brooklyn, DUMBO and Brooklyn Bridge 

Option – Cityline Night Cruise


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