How to spend 4 days in New York City with Itinerary

New York, New York…the city I can’t get enough of.

Seriously, every year I want to “pop” over the pond for a long weekend of shopping, eating and pretending I am Carrie Bradshaw. I love the buzz of the city.

The city that never sleeps is always evolving and there is always something new to do and see, it can be tricky deciding how to maximise your time. I believe that in four days you can tick a lot of bucket list items off and still have room to wander the less beaten tracks. 

The best way to navigate your way around NYC is to break up your days into Neighbourhoods and spend each day in and around these areas to maximise the most of your time.

Source | Roxy Hotel

Source | Roxy Hotel

The Roxy Hotel | Tribeca 

I love Jazz, and this hotel has all the feels, with live Jazz every night in their underground bar called The Django. Complimentary Champagne on arrival and even a pet goldfish if you're missing home. In the Top 20 Hotels in NYC on Trip Advisor and at $200 a night, now that's affordable luxury! 


Day 1 - New York Itinerary

Midtown and Central Park 

The first day is all about ticking off the iconic New York attractions, well those in Midtown and near to Central Park anyway. Depending where your hotel is, you may move the day around to suit your location better.

Times Square

I remember the first time I stood in Times Square and it felt so surreal, having watched so many films use it as a backdrop. You can have a mooch around here as it won’t be as busy as midday onwards.

Grand Central Station

Again, a precious staple of Hollywood. I was lucky to get the train from Westport into Grand Central Station which was extra special. Take a moment to look around the amazing architecture and you can even have incredible Oysters here.

New York Public Library

I love heading to the library, it reminds me of Ghostbusters. Founded

You can visit as part of a guided tour for free. These leave the Astor Hall at 11am and 2pm; Monday - Saturday and 2pm on Sundays.

Rockefeller Centre

It’s hard decided which view point is better but having been up the Empire State and Rockefeller, I think Rockefeller wins.

You get the best of both worlds. Central Park and the views onto the Empire State. It’s unbelievable how huge Central Park is until you see it from above.

Tickets - $38pp for a trip to the Observation Deck. You can also get Sun & Stars package which means you can visit in the day and at night over 24 hours, costing $56.


A paradise for Italianophiles . You can shop as well as eat.

Choose between fresh pasta, seafood, antipasti and wine, so much wine. It’s the perfect spot for lunch.

Flatiron Building

Near to Eataly is the impressive Flatiron building.


The choice of museums is ridiculous. New York has so many and so many good ones at that.

My favourite is the Natural History Museum. I thoroughly enjoy whiling hours away here. The Dark Universe show was pretty spectacular.

A New York Bus Driver told me a hack for the Museums. A lot of them are suggested donations not ticketed. He said you can pay the suggest donation, a little less or even nothing. It’s up to you. For the record, I paid the suggested donation but in case your short on cash if you give something, I am sure they will be happy.

Tavern on the Park

After a long day of walking, finishing up in Central Park and having a lovely drink at the Tavern on the Park is pure bliss.

In the evening, it’s tree strewn lights, illuminate the tables and make a romantic spot to relax.

Rooftop View Drinks

If you fancy a late night, head to Bar Sixty-five for Rooftop Views of the Empire State. You can sample cocktails from NYC’s top mixologists. Cocktails will set you back $20 a glass but my god those views are worth right?

Day Two - New York Itinerary

Itinerary for Greenwich Village & Chelsea 

It's time to feel like Carrie in Sex in the City and strut your way around the Village.

I have to admit, this neighbourhood is my favourite as I feel like I have left the hustle and bustle of NYC and walked into a suburban town miles away. Plus anywhere with Brownstone and cute cafes and I’m hooked. 

Washington Square Park

The pinnacle of Greenwich is Washington Square Park. The eagled eyed 80’s film buffs will recall the Arch from When Harry Met Sally. It’s such a nice way to begin the day and it’s a great starting point for exploring the surrounding area.

Eat and Drink

  • By Chloe Cafe for Brunch

  • Jack's Wife Freda and Olio e Piu restaurant

  • Magnolia Bakery

  • Laughing Man Coffee - Hugh Jackson's nod to Coffee. I have read a many good article about his cup of Joes so cannot wait to get my mitts on one.

  • Baked - the hype around this bakery is insane. I will be off to sample a pastry or two.

  • Airs Champagne Bar and Amelie Wine Bar

  • Employees Only Speakeasy Cocktail Bar

  • Carbone for dinner

  • Little Owl for lunch

  • Spotted Pig for dinner

  • Gallow Green Cocktail Bar

  • Gansevoort and Chelsea Markets

  • Bubby's for Brunch

Chelsea Market

When I visited Chelsea Market, I was floored. I wasn’t expecting much but it turned out to be one of my favourite highlights. We visited in the Fall and the decorations were incredible.

Firstly, it’s undercover which is perfect if the heavens open and it’s full of shops, cafés and restaurants.

If you’re looking for a pick-me-up then this place will have something to end those belly groans. Jamaican, Japanese, Mexican, American, Italian, yes, you name it, they have it!

Gansevoort Market

Gansevoort Market is close to Chelsea but in terms of architectural buildings, this one is cool. Hailing back to 1884 when the first open air market opened, it has all the history and local food.

Much like Chelsea Market, it serves up delicacies from all over the worls but usually sourced locally. It’s not as big as Chelsea but with that, it means less crowds to tackle.

High Line

Want to walk amongst the high rise buildings on a disused rail track, full of view points, plants and sculptures? Who doesn’t?!

The High Line is a breath of fresh air and such a nice way of taking five from the hectic world around you. It’s 1.45 miles long so doesn’t take too long to walk. A great way to walk off food consumed at Chelsea or Gansevoort Markets.

Open 7am - 10pm daily and it’s free what a bonus.

Catch a Game

A must do, even if you do not like sport is to watch a Knicks game at Madison Square Garden. I absolutely loved it, bearing in mind, I do not follow Basketball or understand a thing (does Netball count?)

The atmosphere and the fans made it for me. I laughed, chanted and drank lots of Blue Moon and had the best evening.

Day Three - New York Itinerary

Itinerary for Soho & East Village

I cannot stress enough how much I love Lower Manhattan and hopefully by spending the past two days down town you will too.


Let’s shop til we drop! No trip to NYC could be complete without parting with some dollar, right?

Noho is my favourite part of NYC to shop as it literally has everything you can think of.

Canal Street

Broadway Street

Lafayette Street

Please Don't Tell Me Speakeasy Cocktail Bar

Egg Shop Brunch

  • Mother's Ruin

  • Macbar (Mac and Cheese Cafe)

  • Katz Deli


Day Four - New York Itinerary

Itinerary for Brooklyn and Williamsburg

Again areas I have yet to properly gandered round

  • I found Catbird last time, which has the cutest jewellery I've seen, so will be saving for a cheeky purchase here.

  • Pink Olive is a serious love of mine. I am a stationery addict! This cute Williamsburg store has brands like Rifle Paper and local artists. What more can a girl ask for.

  • Walk over Brooklyn Bridge to DUMBO

  • Dough (Doughnuts)

  • Grimaldi's Pizza

  • The Bagel Store

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