5 Days in New York.

by Charlie - Where Charlie Wanders

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5 days in New York itinerary

I have now visited New York 3 times, and if possible, it just keeps getting better.

image of graffiti in New York

Going back for the third time means you feel you know it that bit better and had a much clearer idea of what you want to achieve from a trip. Aside from all the eating and drinking that will occur (blog post on this here) here are some experiences to help you get a little bit deeper in the city.


Brooklyn bridge is an iconic of New York, however this is not the only way to arrive into Brooklyn. If you wanting to walk into Brooklyn over a different path and try Williamsburg Bridge. If it is a snowy day it is magical. But even if it is not the industrial bridge is just so striking. For an alternative trip into this part of New York, this is a really cool option. I would love to spend more time exploring Williamsburg.

Image of Williamsburg Bridge in New York

After this, walk towards DUMBO (so called because: Down Under Manhattan Bridge Overpass), another really cool and exciting part of Brooklyn.

Image of Manhattan Bridge from DUMBO in New York

Then from there to Brooklyn Heights. A real recommended highlight is heading down to Brooklyn Heights Promenade; the view of the city is just breathtaking. It offers views of such iconic New York scenes. Best viewed at sunset. On the day I went the snow storm that had clouded the whole day had cleared and it was the most marvellous light.

Image of Brooklyn Heights promenade in New York


At this point, we had succumbed to the cold and took shelter in the nearest bar. It was dark by the time we emerged, so decided to save walking back across Brooklyn Bridge for another day and took the metro back into Manhattan.

Brooklyn Bridge – cliched? Sure. But well worth it for those views of Manhattan. If you want to see those iconic views of the Manhattan skyline then consider walking from Brooklyn back into the city.

image of Brooklyn bridge and new York

The Whitney

Even if you are not particularly interested in heading to any of the museums, make this one your exception: The Whitney. Now, even if me you are not an art buff (I have to confess a lot of art often goes over my head) however you can still really enjoy this museum. It was showing a fantastic exhibit by an artist called Laura Owens and it was so absorbing. If you are tempted to visit any of Manhattan’s culture spots, this is one that is highly recommend.

image of art in the Whitney in New York

The Highline

The Whitney is right next to the High Line and together they are the perfect combination for a wonderful day in the Meatpacking District. Depending on the weather might affect how much time you want to spend here. On a cold winter’s day, it is worth heading down for a short time. If it is a balmy, summers day then spend hours chilling here. Although make sure you get there early! The Highline was an old rail line, that they have turned into a linear elevated park – and a wonderful spot for seeing views of the Hudson and glimpses of the grid of Manhattan.

Image of the highline in New York

image of meatpacking district in New York from the highline

Uptown New York

For a wonderful afternoon spend time walking up Fifth avenue and  then ending up on the Upper East Side. It is a long and busy walk from the Lower East Side, but worth doing. And any day where you end up Uptown is a good one.

It’s a great walk, and a lengthy one, but you do pass all the necessary New York sights, the Flatiron, Washington Square Park, Empire State, Rockefeller Centre and a quick glimpse of Central Park. Obviously, it also works in the opposite direction depending on where you are staying.

image of the flatiron building in New York

image of the Chrysler building in New York

Central Park

No trip to New York would be complete without visiting Central Park. It is such a favourite place in the city. Spend a day with a picnic and wandering around here, in a much warmer climates or just wandering around and appreciate the scenes. The contrast of this huge open space with the tall buildings towering either side, is so striking. Even if you only have an hour or so in the park it is always worth it. If you are visiting in the winter seeing the lake and the Boathouse in a frozen setting is a big bucket list tick!

image of central park in new York

image of the boat house in Central Park in New York

Fan moment

A little geeky moment – but one for the Friends fans. Take a stroll into the West Village before brunch one morning to have a quick look at the famous façade. It can be found on the corner of Grove Street and Bedford Street.

image of the friends apartment building in west village in New York


One final highly recommended tip is to go and see a basketball game. If you can get tickets to see the Knicks play, the atmosphere is amazing. However, if they are not playing or if you are looking for a slightly more budget friendly option then head into Brooklyn to watch the Brooklyn Nets play. Basketball is always such a great atmosphere and even more so when the home team win. The Americans do sport well and it makes for such a great evening. It is easy to pick up the rules, I promise.

image of the Brooklyn nets in New York

The Subway

Managing to fit in all the above was busy but there were two things will make this trip easier.

Firstly get to grips with the Metro. Take a few wrong turns and there will be lots of staring at the map – but you will finally understand it. Well, as much as anyone can. It really opens up the city.

image of the subway in New York

You can have up to 4 people travelling on one Metro card, which means it is a cheap way to get around the city and it mean you can go a lot further in a day. For example, nipping to Central Park for an hour, before heading back to the Lower East Side and then out to Brooklyn.

Where to Stay

The second tip to make your trip that little bit easier, is the location of the your hotel.

Try Orchard Street Hotel in the Lower East Side. BOOK BY CLIKCING HERE

Worth it alone as this is the view from the room: Yes, you can lie in bed and see the Empire State.

image of the Empire State building from Orchard Street in New York

It is also in such a good location for so many of the bars and restaurants you will want to visit, as well as a 3 minute walk from two subway stations. Staying in the Lower East Side means it is quieter and feels a bit less touristy.  It is also well located if you want to explore both Manhattan and Brooklyn. If you are looking for something practical and accessible this is your place, I would 100% recommend.

image of Orchard Street Hotel in New York

No matter how many times you visit New York this city always has so much more has to give. In the words of Carrie Bradshaw: ‘I miss New York, take me home’.

Heading to New York? Take a look at these posts:

For where to eat and drink, have a look here.

And for my must see tips for a first visit, check out this post

If you are visiting in Winter – these tips are extremely practical! Take a look here


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quincy harley jr January 11, 2018 - 6:22 pm

😊☹️ As a native ‘New Yawker’ this made me happy and sad, because i also miss it. Though I’ve been away for almost a decade, i was born in that city and lived it for ~40 years; plenty of time for it to get under my nails, into my lungs, lodge into my heart. My path of residency triangulates ‘loisada’, to ‘the heights’, and o’er the river to ‘clinton hill’, so i’ve trod the same steps you did.

thx for the memories

charliewo207 January 11, 2018 - 6:46 pm

Thank you so much! I’m so pleased you enjoyed it, though I am sorry it made you sad. Means a lot to hear these comments from a native! It’s such a special city.

quincy harley jr January 11, 2018 - 6:54 pm


Tilly Horseman January 15, 2018 - 1:27 pm

Wow, the view from that hotel room is superb! You have me pining to visit NYC again. I’ve been twice and love it! Stayed in Mid town both times. Excellent location but v.pricy! Would love to see the highline, and the 9/11 memorial…it was still a building site when I last visited! 💚

Charlie January 15, 2018 - 7:03 pm

It really was amazing! Midtown is good for the sites, but I absolutely loved staying Downtown – it had such a great vibe. Definitely head back soon, I can’t wait until I return!

taliapeace January 20, 2018 - 10:52 am

Oh i want to go to New York so much you don’t understand! Xx Talia

Edward Zazueta April 8, 2018 - 8:36 am

Never seen but it beautiful

Natalie September 17, 2018 - 7:21 pm

Oh, I love New York too! Your images are stunning and I’ve experienced everything that you listed here (apart from the museum, as I’m not really a fan of that kind of thing either). I’ve only ever been in the summer but it always looks beautiful in winter too. I want to go at Christmas but not sure I could handle the cold!!

Charlie - Where Charlie Wanders September 17, 2018 - 8:40 pm

Thank you so much! It was beautiful, but incredibly cold! I do love New York – my favourite city!

Alicia November 17, 2018 - 10:04 pm

Hey Charlie! What a great post! I visited New York for the first time last year and was mesmerised! I have left a huge chunk of my heart in New York too, I don’t think there’s many people that don’t! Love your tips and couldn’t agree more about The High Line – we went in July so it was hot and simply beautiful! Often something I think miss out on! I would love to visit New York in winter your photographs look amazing! Heading to your eating and drinking post now to see what else I can add the list for my next visit!

Charlie - Where Charlie Wanders November 18, 2018 - 8:21 am

Hi Alicia! Thanks so much for the lovely comment. I’m so pleased you enjoyed the post 😊. It is just the most amazing city isn’t it?? I can’t wait to go back. It was beautiful in the winter, but oh so cold! Hope you enjoyed the food and drink post.

melisliving December 17, 2018 - 7:12 pm

I have only been to New York once but loved it so much – we are hoping to go back in 2019 and this is making me so excited at that prospect! Your photos are just fantastic. Melis

Charlie - Where Charlie Wanders December 19, 2018 - 7:25 am

It’s my favourite city! Hope you make it back, I might have to go for work so 🤞🏻

Stefan (Berkeley Square Barbarian) March 29, 2019 - 9:25 pm

Great post. I like that you include a lot of Brooklyn, perhaps our favourite part of NYC, especially around Williamsburg with all its eateries, bars, clubs. 🙂

Charlie - Where Charlie Wanders March 29, 2019 - 9:42 pm

It’s definitely one of my favourite parts of New York!! I think people often miss it on a first trip, so I loved going back and getting time to explore 😊

World of Lina March 30, 2019 - 10:10 am

This is such a helpful itinerary! I will definitely use it for my upcoming NYC trip ☺️

Charlie - Where Charlie Wanders March 30, 2019 - 10:42 am

Thank you! I’m so pleased you found it useful. Have the best time! It’s just the most awesome city!!


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