5 Days in New York: The ultimate guide on what to see and do!

New York, New York – the city so nice they named it twice! Gerard Kenny

New York City is definitely ‘The City that never sleeps‘ and this trendy bustling metropolis has a never-ending list of places to go and sights to see, and so how do you narrow it all down and prioritise what you want to see and do in 5 days?

We faced this dilemma when planning our girl’s trip to ‘The Big Apple’ in June 2019 and after much research this post is essentially what we prioritised to see for this trip, which was so epic, that we are already planning another trip to cover other things that we didn’t have time to do!

It can feel overwhelming deciding on what to do as there is so much choice but I feel much like London, New York is a city that will steal your heart and you will visit over and over again.


Grand Central Terminal Station

The world famous Grand Central Terminal Station with its iconic stairs, impressive high and stunning ceilings and giant clock in the main terminal are all must-sees and I would recommend grabbing a coffee and spending at least 20 minutes here, taking it all in, people watching and experiencing the buzz. It is a great starting point to sightsee from as some of the main sites are a walking distance away.

Top of the Rock at the Rockefeller Plaza

For the best views of the New York skyline head to ‘Top of the Rock’ at the Rockefeller Plaza . We experienced it during the day (we got there at around 10:00) but I imagine it is also magical during the evening. It offers better views than from the Empire State Building and so if you were choosing between the two I would go with ‘Top of the Rock.’

I was kindly gifted the New York CityPASS, which provides entry to over 100 of the city’s best attractions and tours, and is really convenient, especially if you want to cover a lot of the main sights.

Times Square

Times Square stretches from West 42nd to West 47th Streets and is known for its multitude of Broadway theatres, cinemas and electronic billboards. It is one of those places that make New York a city that never sleeps and great to experience both during the day and at night.

The Oculus

The Oculus at Westfield World Trade Center Mall replaces the PATH station that was destroyed during 9/11 in 2001. It cost 4 billion dollars, making it the most expensive train stop in the world! It represents the most integrated network of underground pedestrian connections in the city with the added bonus of 78,000 square feet of multi level state-of-the-art retail and dining. It is an architectural beauty and next to the 9/11 Memorial site so worth having a look at when planning a visit to the memorial site.

9/11 Memorial Site

I think 9/11 is firmly etched in everyone’s minds and everyone remembers that day vividly. On my last visit to New York the memorial site was still being built and so I was pleased to be able to see it completed on this trip. It is so peaceful and poignant, with a field of trees and two large, recessed pools, the footprints of the original Twin Towers, designed by Michael Arad and called “Reflecting Absence.”
The names of all the victims are inscribed around the pools and you are encouraged to touch the names. It is a really fitting tribute, a sobering experience and it is free to visit.
If you want to visit the museum you have to get tickets and the queues are really long so plan accordingly.

Staten Island Ferry

The Staten Island ferry is a 24 hour commuter ferry that shuttles back and forth from The Whitehall Terminal at the tip of Manhattan to the St. George Terminal on Staten Island, taking around 25 minutes each way, and best of all, it is free!

Avoid rush hour to have the best experience. You will be treated to views of Lower Manhattan, the Statue of Liberty and Ellis Island, Governors Island, and in the distance, Brooklyn.

 The Vessel

Taking inspiration from Indian step-wells is British designer Thomas Heatherwick’s new controversial copper giant sculpture which is undoubtedly a visual highlight at New York’s Hudson Yards, named Vessel.
Heatherwick’s idea was to invert the stepwell’s appearance into a structure that would reach skyward, and form a bowl or ‘vessel’ shape.⠀

It feels and looks like a beehive with its open air series of staircases designed in a honeycomb-like structure with a “choose your own adventure” vibe. ⠀

It consists of 154 staircases, nearly 2,500 steps and 80 different landing spaces, each providing a unique view of the structure itself and of the city. ⠀

Fun fact – it is taller than the statue of liberty, heavier than 600 yellow cabs and has more steps than the Eiffel Tower!⠀

Walk the Highline

Adjacent to The Vessel is The High Line, a disused railway track repurposed as a public park with green foliage and perfect for a stroll. There are various exits and we managed to walk all the way to Central Park after a little walk on The High Line and exiting at one of the stops.

Central Park

Central Park is one of the most stunning public parks in the world, has been featured in many a TV show or movie, and is the heart and soul of New York City. Here you can walk and see musicians performing, horse and carriages going by, wedding photo shoots in progress and dog walkers, whilst locals picnic on the side, or pause with a cup of coffee. You can rent and ride a bike through the park if you wish.

I recommend lunch at The Loeb Boathouse, the only Manhattan restaurant and bar right on a lake, for a scenic lunch. Book in advance to avoid disappointment.

Flatiron Building

One of New York’s much loved and heavily photographed landmarks, The Flatiron Building with its distinctive triangular shape was designed by Chicago architect Daniel Burnham and built in 1902, allowed it to fill the wedge-shaped property located at the intersection of Fifth Avenue and Broadway.

It’s original purposes was to serve as offices for the George A. Fuller Company, a major Chicago contracting firm.

Walk the Brooklyn Bridge

Wander down the world-famous Brooklyn Bridge to take in the breathtaking skyline of NYC. Either get yourself to Brooklyn and walk back to Manhattan or go from Manhattan to Brooklyn.

‘A slice of Brooklyn Pizza Tour’

Aside from the amazing aspect that you are eating slices of delicious Neapolitan pizza made in a coal-fired brick oven at Grimaldi’s (without waiting in the queue which is a major bonus) and L&B Spumoni Gardens for Sicilian pizza, this tour is a fantastic way to learn more about Brooklyn and to see sites where various famous scenes in movies have been shot, learn about some of the history of Brooklyn and seeing some seriously swanky houses, all with an amazing tour guide!

If you are ever in NYC and want to do a fun and interesting tour of Brooklyn, I would highly recommend this one!

As part of the tour you also also walk the iconic Coney Island Boardwalk and at the start of the tour you will get the best photo opportunity at a park near the base of Brooklyn Bridge for views of Manhattan.

I was kindly gifted this experience by A Slice of Brooklyn Bus Tours.

To find out more about their range of tours visit https://www.asliceofbrooklyn.com/

Eat at Ellen’s Stardust Diner

For the American experience I recommend eating at a Diner at least once and the most fun one is Ellen’s Stardust Diner where you can eat classic Diner food whilst listening to singing waitstaff.

Visit The Fleur Room for a Rooftop Bar experience

As dusk falls, head to one of New York’s rooftop bars for night time views of the twinkling sky line. Word of caution, after 8 many get booked for private events so make sure to check ahead of going!

We had a firm favourite – the The Fleur Room at The Moxy NYC Chelsea. The venue is stunning, views incredible, cocktails delicious and music fantastic – so good we went twice till 4am!

Ride the Subway

Cheap and easy to navigate, riding the Subway is a must! Especially to save time when sightseeing.

Try Taiyaki’s Fish-Shaped Ice Cream Cones!

Not just beautiful to look at, these Fish-Shaped Ice Cream Cones by Taiyaki in China Town, taste incredible, and a welcome respite on a hot sunny day! The cones itself (which taste like waffles) are absolutely divine, filled with red bean paste, and so make sure you eat it all.

Try the Bloody Mary at St Regis New York

Did you know the Bloody Mary was invented in 1934, by barman Fernand Petiot, who perfected the recipe for a vodka-and-tomato juice cocktail, at The St. Regis New York’s King Cole Bar. It was renamed the “Red Snapper” so as not to offend the hotel’s refined clientele, and now you can find destination specific variants at St Regis hotels around the world, my favourite being Mauritius. The New York one wasn’t the best I have had but worth a try nevertheless!

Wall Street and The Charging Bull

The Charging Bull, a bronze sculpture by artist Arturo Di Modica, can be found near Wall Street in Downtown Manhattan in the financial district. It has become the symbol of Wall Street and the Financial District and rumour has it that you get good luck if you rub it’s private bits. Leave that one up to you to decide if you want to!

Watch a Broadway Show

You may know the saying, “when in Rome…” But when in New York, seeing a Broadway show is absolutely one of the unmissable things you need to add to your plans. We watched Chicago but there are plenty of choices available. For best seats book early!

Watch a Baseball game

On a previous trip to New York we went to see a Baseball game and the experience was just so amazing I would recommend it to anyone. More than the game itself I loved the atmosphere in the audience and it was great fun!

Have you been to New York?

What are your favourite things to see and do?xx

Thanks to A Slice of Brooklyn Bus Tours for hosting us on the A slice of Brooklyn Pizza Tour and to New York CityPass for gifting us the pass. The rest of the trip was funded by us.

Foodies100 Index of UK Food Blogs


Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.


  1. Bejal wrote:

    Yes to all of these and great guide to NYC! The thing is once is never enough and even three times isn’t! I have never tried the Bloody Mary though!

    Posted 7.8.19 Reply
  2. I just can’t wait for our second trip!

    Posted 7.8.19 Reply
  3. You fit in so many amazing things! I’ve never heard of The Vessel, what an incredible piece of architecture.

    Posted 7.9.19 Reply
  4. What a fabulous list of what to do in NYC. I have been twice and done some of these things but next time I think I am going to make your post my complete wish list. Stunning photography too.

    Posted 7.9.19 Reply
  5. Neha wrote:

    Oh these New York guides are really good! Love the facts in this post. I know where to check back when I eventually go to New York. Baseball game is so on my list

    Posted 7.10.19 Reply
  6. The Purley Girly wrote:

    I love NYC so much, I last went in 2016 and I miss it terribly. So many amazing things to see and do there, I don’t think I would ever get tired of it.

    Posted 7.18.19 Reply
  7. kerry wrote:

    I loved reading this Binny. I have not been back to New York for 5 years, so this has made me excited to go again! The 9-11 memorial had been built when I last went, but not the Occulus. The tour looks fab!

    Posted 7.21.19 Reply
  8. Laura wrote:

    This has definitely made me want to go back!

    Posted 8.3.19 Reply
  9. Tammy wrote:

    As amazing as all of this is, I’m so glad you mentioned Ellen’s Stardust Diner!!! We loved the theatrics and singing!! I have not experienced night life of NYC (except Times Square) because I was with 2 teens, but I’d love to! Oh well, I guess I’ll have to go back!!! I love this post! You’ve encouraged me to want to start writing again!

    Posted 7.21.20 Reply
error: Content is protected !!